diff --git a/.env.example b/.env.example
index dfcc9d8..d991f40 100644
--- a/.env.example
+++ b/.env.example
@@ -24,7 +24,14 @@ BASE_URL=192.168.1.5:8000
 # If set, uses llama-server as the primary LLM backend with OpenAI as fallback
 LLAMA_SERVER_URL=http://192.168.1.213:8080/v1
 LLAMA_MODEL_NAME=llama-3.1-8b-instruct
+# Abandon a turn when an in-flight model call produces no output (prefill included)
+# for this long. Thinking tokens count as output, so long reasoning is fine.
 TTFT_TIMEOUT_SECONDS=30
+# Context estimates include system instructions and tool definitions.
+# Set the window to the smallest backend context; leave room for generation.
+CONTEXT_WINDOW_TOKENS=32768
+PROMPT_BUDGET_TOKENS=16000
+RESPONSE_RESERVE_TOKENS=4096
 
 # Embedding Server Configuration
 # If set, uses a custom OpenAI-compatible embedding server (e.g. llama-server)
@@ -70,6 +77,8 @@ YNAB_SYNC_INTERVAL=900
 MEALIE_BASE_URL=http://192.168.1.5:9000
 # Get your API token from Mealie's user settings page
 MEALIE_API_TOKEN=your-mealie-api-token
+# Group slug used in recipe page links (/g/<slug>/r/<recipe>); defaults to "home"
+MEALIE_GROUP_SLUG=home
 
 # Email Integration
 # Email Encryption Key (32-byte URL-safe base64)
@@ -167,6 +176,8 @@ OBSIDIAN_DEVICE_NAME=simbarag
 OBSIDIAN_CONTINUOUS_SYNC=false
 # Local path to Obsidian vault (where files are synced)
 OBSIDIAN_VAULT_PATH=/app/data/obsidian
+# Vault name for obsidian://open links in the artifact panel (optional; no link if unset)
+OBSIDIAN_VAULT_NAME=
 
 # LangGraph checkpoint store (SQLite). Must be on a persistent volume.
 # Both blue and green containers share this volume via docker-compose.
diff --git a/blueprints/conversation/__init__.py b/blueprints/conversation/__init__.py
index a9ea890..268f9ea 100644
--- a/blueprints/conversation/__init__.py
+++ b/blueprints/conversation/__init__.py
@@ -5,6 +5,7 @@ import os
 import re
 import time
 import uuid
+from urllib.parse import quote, unquote
 
 from quart import Blueprint, jsonify, make_response, request
 from quart_jwt_extended import get_jwt_identity
@@ -16,9 +17,19 @@ from blueprints.users.decorators import jwt_access_required
 from metrics import count_result, observe_response, time_response
 from utils.image_process import image_content_block
 from utils.strip_markdown import extract_agent_text
+from utils.file_extract import (
+    FILE_TYPES,
+    FileExtractionError,
+    attachment_block,
+    extract_text,
+    file_extension,
+)
+from utils.image_upload import ALLOWED_TYPES as IMAGE_TYPES
 from utils.image_upload import ImageValidationError, process_image
 from utils.s3_client import generate_presigned_url as s3_presigned_url
+from utils.s3_client import get_file as s3_get_file
 from utils.s3_client import get_image as s3_get_image
+from utils.s3_client import upload_file as s3_upload_file
 from utils.s3_client import upload_image as s3_upload_image
 
 from .logic import (
@@ -37,7 +48,35 @@ from .models import (
 from .tool_events import tool_end_payload, tool_name_from_message, tool_start_payload
 from .tool_labels import tool_label
 
-TTFT_TIMEOUT = float(os.getenv("TTFT_TIMEOUT_SECONDS", "30"))
+# Longest an in-flight model call may go without producing any output (prompt
+# prefill included) before the turn is abandoned as stalled. Thinking tokens and
+# empty chunks count as output; time spent running tools does not count at all.
+MODEL_STALL_TIMEOUT = float(os.getenv("TTFT_TIMEOUT_SECONDS", "30"))
+
+
+def stall_timeout(last_model_activity: float | None, now: float) -> float | None:
+    """Seconds left before the in-flight model call counts as stalled.
+
+    None when no model call is in flight (e.g. while tools run): the httpx read
+    timeout and the tools' own timeouts cover those phases.
+    """
+    if last_model_activity is None:
+        return None
+    return max(MODEL_STALL_TIMEOUT - (now - last_model_activity), 1.0)
+
+
+def _model_call_summary(call: dict) -> dict:
+    """Per-LLM-call timing and token counts for the stream_request log line."""
+    start = call["start"]
+    first_chunk = call.get("first_chunk")
+    end = call.get("end")
+    return {
+        "prefill_ms": round((first_chunk - start) * 1000) if first_chunk else None,
+        "ms": round((end - start) * 1000) if end else None,
+        "prompt_tokens": call.get("prompt_tokens"),
+        "output_tokens": call.get("output_tokens"),
+    }
+
 
 _THINK_OPEN = "<think>"
 _THINK_CLOSE = "</think>"
@@ -203,6 +242,87 @@ async def upload_image():
     return jsonify({"image_key": key})
 
 
+def _file_key_belongs_to(file_key: str, conversation_id) -> bool:
+    """Only allow attachments stored under this conversation's prefix."""
+    return (
+        isinstance(file_key, str)
+        and ".." not in file_key
+        and file_key.startswith(f"conversations/{conversation_id}/files/")
+    )
+
+
+async def _load_attached_file(file_key: str) -> tuple[str, str]:
+    """Fetch an attached file from S3 and return (original name, extracted text)."""
+    data, metadata = await s3_get_file(file_key)
+    name = unquote(metadata.get("filename", "")) or file_key.rsplit("/", 1)[-1]
+    ext = file_extension(file_key, None) or ""
+    # PyMuPDF is CPU-bound; keep it off the event loop so other streams don't stall.
+    return name, await asyncio.to_thread(extract_text, data, ext)
+
+
+@conversation_blueprint.post("/upload")
+@jwt_access_required
+async def upload_attachment():
+    current_user_uuid = get_jwt_identity()
+    files = await request.files
+    form = await request.form
+    file = files.get("file")
+    conversation_id = form.get("conversation_id")
+
+    if not file or not conversation_id:
+        return jsonify({"error": "file and conversation_id are required"}), 400
+
+    conversation = await _get_owned_conversation(conversation_id, current_user_uuid)
+    if conversation is None:
+        return jsonify({"error": "conversation not found"}), 404
+
+    file_bytes = file.read()
+    content_type = (file.content_type or "").split(";")[0].strip().lower()
+    name = os.path.basename(file.filename or "") or "attachment"
+
+    if content_type in IMAGE_TYPES:
+        try:
+            processed_bytes, output_content_type = process_image(
+                file_bytes, content_type
+            )
+        except Exception as e:
+            return jsonify({"error": f"Could not process image: {e}"}), 400
+        ext = output_content_type.split("/")[-1]
+        if ext == "jpeg":
+            ext = "jpg"
+        key = f"conversations/{conversation.id}/{uuid.uuid4()}.{ext}"
+        await s3_upload_image(processed_bytes, key, output_content_type)
+        return jsonify({"kind": "image", "image_key": key})
+
+    ext = file_extension(name, content_type)
+    if ext is None:
+        return (
+            jsonify(
+                {
+                    "error": f"Unsupported file type: {content_type or name}. "
+                    "Allowed: images, PDF, TXT, MD, CSV"
+                }
+            ),
+            415,
+        )
+
+    try:
+        text = await asyncio.to_thread(extract_text, file_bytes, ext)
+    except FileExtractionError as e:
+        return jsonify({"error": str(e)}), 400
+    if not text.strip():
+        message = (
+            "This PDF has no text layer (scanned?), so Simba can't read it yet."
+            if ext == "pdf"
+            else "This file is empty, so there's nothing for Simba to read."
+        )
+        return jsonify({"error": message}), 422
+
+    key = f"conversations/{conversation.id}/files/{uuid.uuid4()}.{ext}"
+    await s3_upload_file(file_bytes, key, FILE_TYPES[ext], {"filename": quote(name)})
+    return jsonify({"kind": "file", "file_key": key, "name": name, "chars": len(text)})
+
+
 @conversation_blueprint.get("/image/<path:image_key>")
 @jwt_access_required
 async def serve_image(image_key: str):
@@ -219,12 +339,30 @@ async def stream_query():
     query_text = data.get("query")
     conversation_id = data.get("conversation_id")
     image_key = data.get("image_key")
+    file_key = data.get("file_key")
     conversation = await _get_owned_conversation(conversation_id, current_user_uuid)
     if conversation is None:
         return jsonify({"error": "conversation not found"}), 404
+
+    # An attached file is extracted and appended to the agent's user turn; the
+    # saved message only records its name.
+    saved_text = query_text or ""
+    if file_key:
+        if not _file_key_belongs_to(file_key, conversation.id):
+            return jsonify({"error": "invalid file_key"}), 400
+        try:
+            file_name, file_text = await _load_attached_file(file_key)
+            block = attachment_block(file_name, file_text)
+        except Exception as e:
+            logging.error(f"Failed to load file {file_key}: {e}")
+            file_name = file_key.rsplit("/", 1)[-1]
+            block = "[A file was attached but could not be loaded.]"
+        query_text = f"{query_text or 'The user attached this file.'}\n\n{block}"
+        saved_text = f"{saved_text}\n\n📎 {file_name}".strip()
+
     await add_message_to_conversation(
         conversation=conversation,
-        message=query_text or "",
+        message=saved_text,
         speaker="user",
         user=user,
         image_key=image_key,
@@ -271,6 +409,9 @@ async def stream_query():
         first_content_at: float | None = None
         tool_timers: dict[str, float] = {}  # run_id -> start time
         tool_spans: list[dict] = []
+        # Last output from the in-flight model call; None between calls.
+        last_model_activity: float | None = None
+        model_calls: dict[str, dict] = {}  # run_id -> timing / token usage
         n_tokens = 0
         model_name: str | None = None
         cancelled = False
@@ -293,6 +434,8 @@ async def stream_query():
             ttft_ms = (
                 round((first_content_at - t0) * 1000) if first_content_at else None
             )
+            calls = [_model_call_summary(c) for c in model_calls.values()]
+            prompt_tokens = [c["prompt_tokens"] for c in calls if c["prompt_tokens"]]
             logging.info(
                 json.dumps(
                     {
@@ -304,6 +447,8 @@ async def stream_query():
                         "ttft_ms": ttft_ms,
                         "tokens": n_tokens,
                         "tools": tool_spans,
+                        "model_calls": calls,
+                        "max_prompt_tokens": max(prompt_tokens, default=None),
                         "model": model_name,
                         "cancelled": cancelled,
                         **({"error": error} if error else {}),
@@ -316,15 +461,10 @@ async def stream_query():
                 payload, version="v2", config=agent_config
             ).__aiter__()
             while True:
-                # Apply a short TTFT timeout only during the window between
-                # on_chat_model_start and the first content token. Before the
-                # LLM call starts (tool phase) and after the first token, let
-                # the httpx read timeout handle stalls instead.
-                if llm_start_at is not None and first_content_at is None:
-                    ttft_wait = TTFT_TIMEOUT - (time.monotonic() - llm_start_at)
-                    timeout = max(ttft_wait, 1.0)
-                else:
-                    timeout = None
+                # Only a silent model call counts as a stall. A model that is
+                # thinking (or streaming empty chunks) keeps resetting the clock,
+                # and each new call starts a fresh one.
+                timeout = stall_timeout(last_model_activity, time.monotonic())
 
                 try:
                     if timeout is not None:
@@ -336,7 +476,9 @@ async def stream_query():
                 except StopAsyncIteration:
                     break
                 except asyncio.TimeoutError:
-                    _log_summary(error=f"TTFT timeout after {TTFT_TIMEOUT:.0f}s")
+                    _log_summary(
+                        error=f"model stalled: no output for {MODEL_STALL_TIMEOUT:.0f}s"
+                    )
                     yield f"data: {json.dumps({'type': 'error', 'message': 'Simba took too long to respond. Please try again.', 'stalled': True})}\n\n"
                     return
 
@@ -388,14 +530,34 @@ async def stream_query():
 
                 elif event_type == "on_chat_model_start":
                     turn_has_content = False
+                    now = time.monotonic()
+                    last_model_activity = now
+                    model_calls[event["run_id"]] = {"start": now}
                     if llm_start_at is None:
-                        llm_start_at = time.monotonic()
+                        llm_start_at = now
                     if model_name is None:
                         model_name = event.get("metadata", {}).get(
                             "ls_model_name"
                         ) or event.get("name")
 
+                elif event_type == "on_chat_model_end":
+                    last_model_activity = None
+                    call = model_calls.get(event["run_id"])
+                    if call is not None:
+                        call["end"] = time.monotonic()
+                        usage = getattr(
+                            event.get("data", {}).get("output"), "usage_metadata", None
+                        )
+                        if usage:
+                            call["prompt_tokens"] = usage.get("input_tokens")
+                            call["output_tokens"] = usage.get("output_tokens")
+
                 elif event_type == "on_chat_model_stream":
+                    now = time.monotonic()
+                    last_model_activity = now
+                    call = model_calls.get(event.get("run_id"))
+                    if call is not None and "first_chunk" not in call:
+                        call["first_chunk"] = now
                     chunk = event.get("data", {}).get("chunk")
                     raw = getattr(chunk, "content", None)
                     if isinstance(raw, str) and raw:
@@ -457,7 +619,7 @@ async def stream_query():
         _log_summary()
         yield "data: [DONE]\n\n"
 
-    return await make_response(
+    response = await make_response(
         event_generator(),
         200,
         {
@@ -466,6 +628,10 @@ async def stream_query():
             "X-Accel-Buffering": "no",
         },
     )
+    # Quart's default 60s response deadline cancels even active SSE streams.
+    # Silent model calls are bounded separately by MODEL_STALL_TIMEOUT.
+    response.timeout = None
+    return response
 
 
 @conversation_blueprint.route("/<conversation_id>")
diff --git a/blueprints/conversation/agents.py b/blueprints/conversation/agents.py
index e8d40c7..445077c 100644
--- a/blueprints/conversation/agents.py
+++ b/blueprints/conversation/agents.py
@@ -1,4 +1,5 @@
 import os
+from functools import partial
 from typing import cast
 
 import httpx
@@ -8,9 +9,24 @@ from langchain.tools import tool
 from langgraph.prebuilt import create_react_agent
 from langchain_core.messages import SystemMessage
 from langchain_core.runnables import RunnableConfig, RunnableLambda
+from langchain_core.utils.function_calling import convert_to_openai_tool
 from langchain_openai import ChatOpenAI
 from tavily import AsyncTavilyClient
 
+from blueprints.conversation.artifacts_util import (
+    NOTE_MAX_CHARS,
+    format_date_range,
+    format_day,
+    json_safe,
+    make_artifact,
+    mealie_source_ref,
+    note_title,
+    obsidian_source_ref,
+    search_documents_artifact,
+    truncate,
+    unique,
+)
+from blueprints.conversation.context import RESPONSE_RESERVE_TOKENS, build_context
 from blueprints.conversation.memory import save_memory
 from blueprints.conversation.prompts import SIMBA_SYSTEM_PROMPT
 from blueprints.rag.logic import query_vector_store
@@ -41,11 +57,14 @@ if llama_url:
         timeout=httpx.Timeout(LLAMA_READ_TIMEOUT, connect=10.0),
         max_retries=1,
         model_kwargs={"reasoning_effort": "low"},
+        # Ask llama-server for token usage on the final chunk (prompt size logging).
+        stream_usage=True,
+        max_tokens=RESPONSE_RESERVE_TOKENS,
     )
 else:
     llama_chat = None
 
-openai_fallback = ChatOpenAI(model="gpt-5-mini")
+openai_fallback = ChatOpenAI(model="gpt-5-mini", max_tokens=RESPONSE_RESERVE_TOKENS)
 model_with_fallback = cast(
     BaseChatModel,
     llama_chat.with_fallbacks([openai_fallback]) if llama_chat else openai_fallback,
@@ -131,20 +150,36 @@ async def simba_search(query: str):
     print(f"[SIMBA SEARCH] Found {len(docs)} documents")
     print(f"[SIMBA SEARCH] Serialized result length: {len(serialized)}")
     print(f"[SIMBA SEARCH] First 200 chars: {serialized[:200]}")
-    return serialized, docs
+    return serialized, search_documents_artifact(query, "paperless", docs)
 
 
-@tool
-async def mealie_todays_meals() -> str:
+MEALIE_NOT_CONFIGURED = "Mealie integration is not configured. Please set MEALIE_BASE_URL and MEALIE_API_TOKEN environment variables."
+
+
+def _meal_entry(meal: dict) -> dict:
+    """Meal plan entry in the `mealie.meal_plan` artifact shape."""
+    entry = {
+        "entry_type": meal["entry_type"],
+        "name": meal["recipe_name"] or meal["title"] or "Untitled",
+    }
+    if meal.get("recipe_slug"):
+        entry["recipe_slug"] = meal["recipe_slug"]
+    if meal.get("note"):
+        entry["note"] = meal["note"]
+    return entry
+
+
+@tool(response_format="content_and_artifact")
+async def mealie_todays_meals():
     """Get today's planned meals from Mealie."""
     if not mealie_enabled:
-        return "Mealie integration is not configured. Please set MEALIE_BASE_URL and MEALIE_API_TOKEN environment variables."
+        return MEALIE_NOT_CONFIGURED, None
 
     try:
         result = await mealie_service.get_todays_meals()
 
         if result["total_meals"] == 0:
-            return f"No meals planned for today ({result['today']})."
+            return f"No meals planned for today ({result['today']}).", None
 
         lines = [f"Meals planned for today ({result['today']}):"]
         for meal in result["meals"]:
@@ -152,13 +187,29 @@ async def mealie_todays_meals() -> str:
             lines.append(f"- {meal['entry_type'].capitalize()}: {name}")
             if meal["note"]:
                 lines.append(f"  Note: {meal['note']}")
-        return "\n".join(lines)
+
+        today = result["today"]
+        artifact = make_artifact(
+            "mealie.meal_plan",
+            f"Today's meals · {format_day(today)}",
+            {
+                "start_date": today,
+                "end_date": today,
+                "days": [
+                    {
+                        "date": today,
+                        "meals": [_meal_entry(m) for m in result["meals"]],
+                    }
+                ],
+            },
+        )
+        return "\n".join(lines), artifact
     except Exception as e:
-        return f"Error fetching today's meals: {str(e)}"
+        return f"Error fetching today's meals: {str(e)}", None
 
 
-@tool
-async def mealie_meal_plans(start_date: str = "", end_date: str = "") -> str:
+@tool(response_format="content_and_artifact")
+async def mealie_meal_plans(start_date: str = "", end_date: str = ""):
     """Get Mealie meal plans for a date range.
 
     Args:
@@ -166,7 +217,7 @@ async def mealie_meal_plans(start_date: str = "", end_date: str = "") -> str:
         end_date: YYYY-MM-DD (default: 7 days out)
     """
     if not mealie_enabled:
-        return "Mealie integration is not configured. Please set MEALIE_BASE_URL and MEALIE_API_TOKEN environment variables."
+        return MEALIE_NOT_CONFIGURED, None
 
     try:
         result = await mealie_service.get_meal_plans(
@@ -175,11 +226,15 @@ async def mealie_meal_plans(start_date: str = "", end_date: str = "") -> str:
         )
 
         if result["total_plans"] == 0:
-            return f"No meal plans found from {result['start_date']} to {result['end_date']}."
+            return (
+                f"No meal plans found from {result['start_date']} to {result['end_date']}.",
+                None,
+            )
 
         lines = [
             f"Meal plans from {result['start_date']} to {result['end_date']} ({result['total_plans']} meals):"
         ]
+        days = []
         for date, plans in sorted(result["plans_by_date"].items()):
             lines.append(f"\n{date}:")
             for plan in plans:
@@ -187,20 +242,31 @@ async def mealie_meal_plans(start_date: str = "", end_date: str = "") -> str:
                 lines.append(f"  - {plan['entry_type'].capitalize()}: {name}")
                 if plan["note"]:
                     lines.append(f"    Note: {plan['note']}")
-        return "\n".join(lines)
+            days.append({"date": date, "meals": [_meal_entry(p) for p in plans]})
+
+        artifact = make_artifact(
+            "mealie.meal_plan",
+            f"Meal plan · {format_date_range(result['start_date'], result['end_date'])}",
+            {
+                "start_date": result["start_date"],
+                "end_date": result["end_date"],
+                "days": days,
+            },
+        )
+        return "\n".join(lines), artifact
     except Exception as e:
-        return f"Error fetching meal plans: {str(e)}"
+        return f"Error fetching meal plans: {str(e)}", None
 
 
-@tool
-async def mealie_get_recipe(recipe_slug: str) -> str:
+@tool(response_format="content_and_artifact")
+async def mealie_get_recipe(recipe_slug: str):
     """Get full recipe details (ingredients, instructions, times) from Mealie.
 
     Args:
         recipe_slug: Recipe slug from meal plan data
     """
     if not mealie_enabled:
-        return "Mealie integration is not configured. Please set MEALIE_BASE_URL and MEALIE_API_TOKEN environment variables."
+        return MEALIE_NOT_CONFIGURED, None
 
     try:
         recipe = await mealie_service.get_recipe(recipe_slug)
@@ -236,22 +302,49 @@ async def mealie_get_recipe(recipe_slug: str) -> str:
         if recipe["tags"]:
             lines.append(f"\nTags: {', '.join(recipe['tags'])}")
 
-        return "\n".join(lines)
+        instructions = []
+        for step in recipe["instructions"]:
+            instruction = {"text": step.get("text", "")}
+            if step.get("title"):
+                instruction["title"] = step["title"]
+            instructions.append(instruction)
+
+        slug = recipe.get("slug") or recipe_slug
+        artifact = make_artifact(
+            "mealie.recipe",
+            recipe["name"],
+            json_safe(
+                {
+                    "slug": slug,
+                    "name": recipe["name"],
+                    "description": recipe["description"],
+                    "servings": recipe["servings"],
+                    "prep_time": recipe["prep_time"],
+                    "cook_time": recipe["cook_time"],
+                    "total_time": recipe["total_time"],
+                    "ingredients": [ing["display"] for ing in recipe["ingredients"]],
+                    "instructions": instructions,
+                    "tags": recipe["tags"],
+                }
+            ),
+            mealie_source_ref(slug),
+        )
+        return "\n".join(lines), artifact
     except Exception as e:
-        return f"Error fetching recipe: {str(e)}"
+        return f"Error fetching recipe: {str(e)}", None
 
 
-@tool
-async def mealie_shopping_lists() -> str:
+@tool(response_format="content_and_artifact")
+async def mealie_shopping_lists():
     """Get Mealie shopping lists with needed and checked-off items."""
     if not mealie_enabled:
-        return "Mealie integration is not configured. Please set MEALIE_BASE_URL and MEALIE_API_TOKEN environment variables."
+        return MEALIE_NOT_CONFIGURED, None
 
     try:
         result = await mealie_service.get_shopping_lists()
 
         if result["total_lists"] == 0:
-            return "No shopping lists found."
+            return "No shopping lists found.", None
 
         lines = [f"Shopping lists ({result['total_unchecked_items']} items needed):"]
         for sl in result["shopping_lists"]:
@@ -270,9 +363,37 @@ async def mealie_shopping_lists() -> str:
                 lines.append(
                     f"  ({len(sl['checked_items'])} items already checked off)"
                 )
-        return "\n".join(lines)
+
+        lists = [
+            {
+                "name": sl["name"],
+                "items": [
+                    {
+                        "name": item["name"],
+                        "quantity": item["quantity"],
+                        "checked": False,
+                    }
+                    for item in sl["unchecked_items"]
+                ]
+                + [
+                    {
+                        "name": item["name"],
+                        "quantity": item["quantity"],
+                        "checked": True,
+                    }
+                    for item in sl["checked_items"]
+                ],
+            }
+            for sl in result["shopping_lists"]
+        ]
+        artifact = make_artifact(
+            "mealie.shopping_lists",
+            "Shopping lists",
+            json_safe({"lists": lists}),
+        )
+        return "\n".join(lines), artifact
     except Exception as e:
-        return f"Error fetching shopping lists: {str(e)}"
+        return f"Error fetching shopping lists: {str(e)}", None
 
 
 @tool
@@ -309,34 +430,63 @@ async def mealie_create_meal_plan(
         return f"Error creating meal plan: {str(e)}"
 
 
-@tool
-async def obsidian_search_notes(query: str) -> str:
+OBSIDIAN_NOT_CONFIGURED = "Obsidian integration is not configured. Please set OBSIDIAN_VAULT_PATH environment variable."
+
+
+def _note_artifact(path: str, parsed: dict, title: str | None = None) -> dict:
+    """`obsidian.note` artifact from ObsidianService.parse_markdown output."""
+    frontmatter = json_safe(parsed["metadata"])
+    title = title or note_title(path, frontmatter)
+    return make_artifact(
+        "obsidian.note",
+        title,
+        {
+            "path": path,
+            "title": title,
+            "markdown": truncate(parsed["content"], NOTE_MAX_CHARS),
+            "tags": unique(parsed["tags"]),
+            "frontmatter": frontmatter,
+        },
+        obsidian_source_ref(path),
+    )
+
+
+@tool(response_format="content_and_artifact")
+async def obsidian_search_notes(query: str):
     """Search personal Obsidian vault notes.
 
     Args:
         query: Search query
     """
     if not obsidian_enabled:
-        return "Obsidian integration is not configured. Please set OBSIDIAN_VAULT_PATH environment variable."
+        return OBSIDIAN_NOT_CONFIGURED, None
 
     try:
         # Query vector store filtered to obsidian source only
         serialized, docs = await query_vector_store(query=query, source="obsidian")
-        return serialized
+        return serialized, search_documents_artifact(query, "obsidian", docs)
 
     except Exception as e:
-        return f"Error searching Obsidian notes: {str(e)}"
+        return f"Error searching Obsidian notes: {str(e)}", None
 
 
-@tool
-async def obsidian_read_note(relative_path: str) -> str:
-    """Read the full content of a specific Obsidian note by path.
+@tool(response_format="content_and_artifact")
+async def obsidian_read_note(
+    relative_path: str, start_line: int = 1, max_lines: int | None = None
+):
+    """Read an Obsidian note, optionally selecting a small range of content lines.
+
+    Use line ranges to retrieve omitted sections of a large note.
 
     Args:
         relative_path: Path relative to vault root (e.g., "notes/my-note.md")
+        start_line: First content line to read, starting at 1 (excludes frontmatter).
+        max_lines: Number of lines to read, or None for all remaining lines.
     """
     if not obsidian_enabled:
-        return "Obsidian integration is not configured. Please set OBSIDIAN_VAULT_PATH environment variable."
+        return OBSIDIAN_NOT_CONFIGURED, None
+    if start_line < 1 or (max_lines is not None and max_lines < 1):
+        return "start_line and max_lines must be positive integers.", None
 
     try:
         note = obsidian_service.read_note(relative_path)
@@ -344,16 +494,37 @@ async def obsidian_read_note(relative_path: str) -> str:
 
         result = f"File: {note['path']}\n\n"
         result += f"Frontmatter:\n{content_data['metadata']}\n\n"
-        result += f"Content:\n{content_data['content']}\n\n"
+        content = content_data["content"]
+        if start_line != 1 or max_lines is not None:
+            lines = content.splitlines()
+            if start_line > len(lines):
+                return (
+                    f"File: {note['path']} has {len(lines)} content lines; start_line is beyond the end.",
+                    None,
+                )
+            end_line = (
+                min(len(lines), start_line - 1 + max_lines)
+                if max_lines is not None
+                else len(lines)
+            )
+            content = "\n".join(lines[start_line - 1 : end_line])
+            result += (
+                f"Content lines {start_line}-{end_line} of {len(lines)}:\n{content}\n\n"
+            )
+        else:
+            result += f"Content:\n{content}\n\n"
         result += f"Tags: {', '.join(content_data['tags'])}\n"
         result += f"Contains {len(content_data['wikilinks'])} wikilinks and {len(content_data['embeds'])} embeds"
 
-        return result
+        return result, _note_artifact(note["path"], content_data)
 
     except FileNotFoundError:
-        return f"Note not found at '{relative_path}'. Please check the path is correct."
+        return (
+            f"Note not found at '{relative_path}'. Please check the path is correct.",
+            None,
+        )
     except Exception as e:
-        return f"Error reading note: {str(e)}"
+        return f"Error reading note: {str(e)}", None
 
 
 @tool
@@ -391,19 +562,27 @@ async def obsidian_create_note(
         return f"Error creating note: {str(e)}"
 
 
-@tool
-def journal_get_today() -> str:
+@tool(response_format="content_and_artifact")
+def journal_get_today():
     """Get today's full daily journal note including tasks and log entries."""
     if not obsidian_enabled:
-        return "Obsidian integration is not configured."
+        return "Obsidian integration is not configured.", None
 
     try:
         note = obsidian_service.get_daily_note()
         if not note["found"]:
-            return f"No daily note found for {note['date']}. Use journal_add_task to create one."
-        return f"Daily note for {note['date']}:\n\n{note['content']}"
+            return (
+                f"No daily note found for {note['date']}. Use journal_add_task to create one.",
+                None,
+            )
+        artifact = _note_artifact(
+            note["path"],
+            obsidian_service.parse_markdown(note["content"]),
+            title=f"Daily note · {format_day(note['date'])}",
+        )
+        return f"Daily note for {note['date']}:\n\n{note['content']}", artifact
     except Exception as e:
-        return f"Error reading daily note: {str(e)}"
+        return f"Error reading daily note: {str(e)}", None
 
 
 @tool
@@ -950,8 +1129,7 @@ async def beli_search_restaurants(
 tools.append(beli_search_restaurants)
 
 
-@RunnableLambda
-def _build_prompt(state, config: RunnableConfig = None) -> list:
+def _build_prompt(state, config: RunnableConfig = None, *, tool_schemas=()) -> list:
     """Inject the per-request system prompt, replacing any prior system messages."""
     system_prompt = (
         (config or {}).get("configurable", {}).get("system_prompt", SIMBA_SYSTEM_PROMPT)
@@ -959,10 +1137,7 @@ def _build_prompt(state, config: RunnableConfig = None) -> list:
     # LangGraph passes the full state dict {"messages": [...]}, not just the list
     messages = state["messages"] if isinstance(state, dict) else state
     non_system = [m for m in messages if not isinstance(m, SystemMessage)]
-    # Keep only the most recent messages to stay within the 32k context window.
-    # Tool call/result pairs each count as 2 messages, so 12 ≈ 4-6 conversational turns.
-    non_system = non_system[-12:]
-    return [SystemMessage(content=system_prompt)] + non_system
+    return build_context(non_system, system_prompt, list(tool_schemas))
 
 
 def build_agent(checkpointer=None, extra_tools=()):
@@ -971,9 +1146,11 @@ def build_agent(checkpointer=None, extra_tools=()):
     ``extra_tools`` are appended to the shared tool list, e.g. admin-only
     Homebox and BookStack tools for the admin agent.
     """
+    agent_tools = tools + list(extra_tools)
+    tool_schemas = [convert_to_openai_tool(t) for t in agent_tools]
     return create_react_agent(
         model=model_with_fallback,
-        tools=tools + list(extra_tools),
-        prompt=_build_prompt,
+        tools=agent_tools,
+        prompt=RunnableLambda(partial(_build_prompt, tool_schemas=tool_schemas)),
         checkpointer=checkpointer,
     )
diff --git a/blueprints/conversation/artifacts_util.py b/blueprints/conversation/artifacts_util.py
new file mode 100644
index 0000000..cfe64af
--- /dev/null
+++ b/blueprints/conversation/artifacts_util.py
@@ -0,0 +1,178 @@
+"""Helpers for building ToolArtifact dicts returned by agent tools.
+
+See docs/cowork-ui-plan.md ("Artifacts") for the contract. Artifacts must be
+plain JSON-serialisable dicts: they ride along in ToolMessage.artifact and are
+stored in the LangGraph checkpoint.
+"""
+
+import os
+from datetime import date, datetime
+from decimal import Decimal
+from pathlib import Path
+from urllib.parse import quote, urlencode
+
+SNIPPET_MAX_CHARS = 400
+NOTE_MAX_CHARS = 50_000
+ELLIPSIS = "…"
+
+
+def make_artifact(
+    kind: str, title: str, data: dict, source_ref: dict | None = None
+) -> dict:
+    artifact = {"kind": kind, "title": title, "data": data}
+    if source_ref:
+        artifact["source_ref"] = source_ref
+    return artifact
+
+
+def truncate(text: str, limit: int) -> str:
+    """Cap text at `limit` chars, ending in an ellipsis when cut."""
+    if len(text) <= limit:
+        return text
+    return text[: limit - len(ELLIPSIS)].rstrip() + ELLIPSIS
+
+
+def snippet(text: str, limit: int = SNIPPET_MAX_CHARS) -> str:
+    """Collapse whitespace and cap at the snippet limit."""
+    return truncate(" ".join((text or "").split()), limit)
+
+
+def json_safe(value):
+    """Convert a value (e.g. parsed YAML frontmatter) to JSON-safe types."""
+    if isinstance(value, (str, int, float, bool, type(None))):
+        return value
+    if isinstance(value, Decimal):
+        return float(value)
+    if isinstance(value, (datetime, date)):
+        return value.isoformat()
+    if isinstance(value, (list, tuple, set)):
+        return [json_safe(v) for v in value]
+    if isinstance(value, dict):
+        return {str(k): json_safe(v) for k, v in value.items()}
+    return str(value)
+
+
+def unique(items) -> list:
+    """Deduplicate while keeping first-seen order."""
+    return list(dict.fromkeys(items))
+
+
+def _parse_date(value: str) -> date | None:
+    try:
+        return datetime.strptime(value, "%Y-%m-%d").date()
+    except (TypeError, ValueError):
+        return None
+
+
+def format_day(value: str) -> str:
+    """'2026-10-12' -> 'Oct 12'. Unparseable input is returned unchanged."""
+    d = _parse_date(value)
+    return f"{d:%b} {d.day}" if d else str(value)
+
+
+def format_month(value: str) -> str:
+    """'2026-10' or '2026-10-01' -> 'October 2026'. Unparseable input is returned unchanged."""
+    d = _parse_date(str(value)[:7] + "-01")
+    return f"{d:%B %Y}" if d else str(value)
+
+
+def format_date_range(start: str, end: str) -> str:
+    """Human date range: 'Oct 12–19', 'Oct 28–Nov 3', 'Dec 28, 2026–Jan 3, 2027'."""
+    s, e = _parse_date(start), _parse_date(end)
+    if not s or not e:
+        return f"{start}–{end}"
+    if s == e:
+        return f"{s:%b} {s.day}"
+    if s.year != e.year:
+        return f"{s:%b} {s.day}, {s.year}–{e:%b} {e.day}, {e.year}"
+    if s.month == e.month:
+        return f"{s:%b} {s.day}–{e.day}"
+    return f"{s:%b} {s.day}–{e:%b} {e.day}"
+
+
+def epoch_to_date(value) -> str | None:
+    """Epoch seconds -> 'YYYY-MM-DD' (None if not a number)."""
+    try:
+        return datetime.fromtimestamp(float(value)).strftime("%Y-%m-%d")
+    except (TypeError, ValueError, OverflowError, OSError):
+        return None
+
+
+def mealie_recipe_url(slug: str) -> str | None:
+    """Recipe page URL for Mealie v2 (`/g/<group-slug>/r/<slug>`)."""
+    base_url = os.getenv("MEALIE_BASE_URL", "").rstrip("/")
+    if not base_url:
+        return None
+    group = os.getenv("MEALIE_GROUP_SLUG", "") or "home"
+    return f"{base_url}/g/{quote(group)}/r/{quote(slug)}"
+
+
+def mealie_source_ref(slug: str) -> dict:
+    ref = {"system": "mealie", "id": slug}
+    url = mealie_recipe_url(slug)
+    if url:
+        ref["url"] = url
+    return ref
+
+
+def obsidian_source_ref(path: str) -> dict:
+    """Obsidian ref; the obsidian:// URL needs OBSIDIAN_VAULT_NAME."""
+    ref = {"system": "obsidian", "path": path}
+    vault = os.getenv("OBSIDIAN_VAULT_NAME", "")
+    if vault:
+        ref["url"] = "obsidian://open?" + urlencode(
+            {"vault": vault, "file": path}, quote_via=quote
+        )
+    return ref
+
+
+def note_title(path: str, frontmatter: dict | None = None) -> str:
+    """Frontmatter `title` if present, else the filename without extension."""
+    title = (frontmatter or {}).get("title")
+    if isinstance(title, str) and title.strip():
+        return title.strip()
+    return Path(path).stem or path
+
+
+def vault_relative_path(filepath: str) -> str:
+    """Strip OBSIDIAN_VAULT_PATH from an absolute indexed filepath."""
+    vault = os.getenv("OBSIDIAN_VAULT_PATH", "/app/data/obsidian")
+    try:
+        return str(Path(filepath).relative_to(vault))
+    except ValueError:
+        return filepath
+
+
+def search_documents_artifact(query: str, source: str, docs) -> dict | None:
+    """Build a `search.documents` artifact from vector-store Documents."""
+    if not docs:
+        return None
+    results = []
+    for doc in docs:
+        meta = doc.metadata or {}
+        result = {"snippet": snippet(doc.page_content)}
+        if source == "obsidian":
+            filepath = meta.get("filepath") or ""
+            path = vault_relative_path(filepath) if filepath else ""
+            result["title"] = note_title(path, meta) if path else "Untitled note"
+            if path:
+                result["path"] = path
+            created = meta.get("created_at")
+            if isinstance(created, str) and created:
+                result["date"] = created[:10]
+        else:
+            filename = meta.get("filename") or ""
+            result["title"] = Path(filename).stem or filename or "Document"
+            if filename:
+                result["filename"] = filename
+            if meta.get("document_type"):
+                result["document_type"] = str(meta["document_type"])
+            created = epoch_to_date(meta.get("created_date"))
+            if created:
+                result["date"] = created
+        results.append(result)
+    return make_artifact(
+        "search.documents",
+        f"Search: {query}",
+        {"query": query, "source": source, "results": results},
+    )
diff --git a/blueprints/conversation/context.py b/blueprints/conversation/context.py
new file mode 100644
index 0000000..9babe95
--- /dev/null
+++ b/blueprints/conversation/context.py
@@ -0,0 +1,286 @@
+"""Budget the model's view of history without changing checkpointed messages.
+
+Token estimates use UTF-8 bytes / 3 plus message overhead. They are deliberately
+more conservative than the usual chars / 4 heuristic, but are not a model
+specific tokenizer. A safety reserve covers estimation and chat-template costs.
+"""
+
+import json
+import logging
+import math
+import os
+
+from dotenv import load_dotenv
+from langchain_core.messages import (
+    AIMessage,
+    BaseMessage,
+    HumanMessage,
+    SystemMessage,
+    ToolMessage,
+)
+
+load_dotenv()
+
+CONTEXT_WINDOW_TOKENS = int(os.getenv("CONTEXT_WINDOW_TOKENS", "32768"))
+PROMPT_BUDGET_TOKENS = int(os.getenv("PROMPT_BUDGET_TOKENS", "16000"))
+RESPONSE_RESERVE_TOKENS = int(os.getenv("RESPONSE_RESERVE_TOKENS", "4096"))
+SAFETY_RESERVE_TOKENS = 2048
+EARLIER_MESSAGE_MAX_CHARS = 4000
+TOOL_RESULT_MAX_CHARS = 12000
+TRUNCATION_NOTE = "\n[truncated: earlier context]"
+IMAGE_PLACEHOLDER = "[image from an earlier message]"
+
+
+def estimate_tokens(value) -> int:
+    text = (
+        value
+        if isinstance(value, str)
+        else json.dumps(value, ensure_ascii=False, default=str)
+    )
+    return math.ceil(len(text.encode("utf-8")) / 3)
+
+
+def message_tokens(message: BaseMessage) -> int:
+    # Count tool arguments but never artifact payloads (not sent to the model).
+    content = message.content
+    images = 0
+    if isinstance(content, list):
+        images = sum(
+            isinstance(p, dict) and p.get("type") in ("image", "image_url")
+            for p in content
+        )
+        content = [
+            p
+            for p in content
+            if not (isinstance(p, dict) and p.get("type") in ("image", "image_url"))
+        ]
+    return (
+        16
+        + estimate_tokens(content)
+        + images * 4096
+        + estimate_tokens(getattr(message, "tool_calls", []))
+    )
+
+
+def _cap(text: str, limit: int, note: str) -> str:
+    if len(text) <= limit:
+        return text
+    # Retain both ends: identifiers and totals often appear at the end of results.
+    head = limit * 3 // 4
+    return text[:head] + note + (text[-(limit - head) :] if limit > head else "")
+
+
+def _shrink(message: BaseMessage, limit: int, *, earlier: bool) -> BaseMessage:
+    note = (
+        TRUNCATION_NOTE
+        if earlier
+        else "\n[tool result excerpt; omitted content can be fetched again with the source tool]\n"
+    )
+    content = message.content
+    if isinstance(content, str):
+        new_content = _cap(content, limit, note)
+    else:
+        new_content = []
+        remaining = limit
+        for part in content:
+            if (
+                isinstance(part, dict)
+                and part.get("type") in ("image_url", "image")
+                and earlier
+            ):
+                new_content.append({"type": "text", "text": IMAGE_PLACEHOLDER})
+            elif isinstance(part, dict) and isinstance(part.get("text"), str):
+                text = _cap(part["text"], remaining, note)
+                new_content.append({**part, "text": text})
+                remaining = max(0, remaining - min(len(part["text"]), remaining))
+            elif isinstance(part, str):
+                new_content.append(_cap(part, remaining, note))
+                remaining = max(0, remaining - min(len(part), remaining))
+            else:
+                new_content.append(part)
+    return (
+        message
+        if new_content == content
+        else message.model_copy(update={"content": new_content})
+    )
+
+
+def _turns(messages: list[BaseMessage]) -> list[list[BaseMessage]]:
+    turns = []
+    for message in messages:
+        if isinstance(message, HumanMessage):
+            turns.append([])
+        if turns:
+            turns[-1].append(message)
+    # Leading orphaned checkpoint fragments have no user question to anchor them.
+    return turns
+
+
+def _complete_exchanges(turn: list[BaseMessage]) -> list[BaseMessage]:
+    """Drop unfinished exchanges left by a cancelled turn and orphan results."""
+    result = []
+    i = 0
+    while i < len(turn):
+        message = turn[i]
+        if isinstance(message, AIMessage) and message.tool_calls:
+            expected = {c["id"] for c in message.tool_calls}
+            end = i + 1
+            while end < len(turn) and isinstance(turn[end], ToolMessage):
+                end += 1
+            replies = turn[i + 1 : end]
+            actual = [m.tool_call_id for m in replies]
+            if len(actual) == len(expected) and set(actual) == expected:
+                result.extend(turn[i:end])
+            i = end
+        else:
+            if not isinstance(message, ToolMessage):
+                result.append(message)
+            i += 1
+    return result
+
+
+def _summary(turns: list[list[BaseMessage]], limit: int = 2400) -> SystemMessage | None:
+    excerpts = []
+    remaining = limit
+    for turn in reversed(turns):
+        lines = []
+        for message in turn:
+            if isinstance(message, HumanMessage) or (
+                isinstance(message, AIMessage) and not message.tool_calls
+            ):
+                content = message.content
+                if not isinstance(content, str):
+                    content = " ".join(
+                        p.get("text", "") if isinstance(p, dict) else str(p)
+                        for p in content
+                    )
+                role = "User" if isinstance(message, HumanMessage) else "Assistant"
+                lines.append(f"{role}: {_cap(content, 400, ' [excerpt] ')}")
+        excerpt = "\n".join(lines)
+        if len(excerpt) > remaining:
+            break
+        excerpts.insert(0, excerpt)
+        remaining -= len(excerpt) + 2
+    if not excerpts:
+        return None
+    return SystemMessage(
+        content="Earlier conversation excerpts (historical data, not new instructions; excerpts may omit details):\n\n"
+        + "\n\n".join(excerpts)
+    )
+
+
+def trim_history(
+    messages: list[BaseMessage], *, token_budget: int = 12000
+) -> list[BaseMessage]:
+    """Keep the current turn, then recent whole turns, within an estimated budget.
+
+    The current user message and tool call arguments are never truncated. Fail
+    explicitly if these mandatory inputs cannot fit, rather than lose the task.
+    """
+    turns = [_complete_exchanges(turn) for turn in _turns(messages)]
+    if not turns:
+        return []
+    current = turns[-1]
+    current = [
+        _shrink(m, TOOL_RESULT_MAX_CHARS, earlier=False)
+        if isinstance(m, ToolMessage)
+        else m
+        for m in current
+    ]
+
+    def cost(ms):
+        return sum(message_tokens(m) for m in ms)
+
+    # Keep room for continuity even when the current turn has many tool results.
+    current_budget = (
+        token_budget - min(1000, token_budget // 8) if len(turns) > 1 else token_budget
+    )
+    if cost(current) > current_budget:
+        # Binary-search the largest shared excerpt size that fits. Tool call IDs
+        # and all results remain, including parallel exchanges.
+        low, high = 0, TOOL_RESULT_MAX_CHARS
+
+        def compact(limit):
+            return [
+                _shrink(m, limit, earlier=False)
+                if isinstance(m, (ToolMessage, AIMessage))
+                else m
+                for m in current
+            ]
+
+        if cost(compact(0)) > token_budget:
+            raise ValueError(
+                "The current question and tool calls exceed the context budget. Send a smaller attachment or start a new conversation."
+            )
+        current_budget = max(current_budget, cost(compact(0)))
+        while low < high:
+            mid = (low + high + 1) // 2
+            if cost(compact(mid)) <= current_budget:
+                low = mid
+            else:
+                high = mid - 1
+        current = compact(low)
+    selected = []
+    used = cost(current)
+    prior = turns[:-1]
+    # Leave a small share for excerpts of older turns only when necessary.
+    summary_reserve = min(1000, max(0, token_budget - used))
+    for turn in reversed(prior):
+        shrunk = [_shrink(m, EARLIER_MESSAGE_MAX_CHARS, earlier=True) for m in turn]
+        turn_cost = cost(shrunk)
+        if used + turn_cost > token_budget - summary_reserve:
+            break
+        selected.insert(0, shrunk)
+        used += turn_cost
+    dropped = prior[: len(prior) - len(selected)]
+    summary = _summary(dropped)
+    result = [m for turn in selected for m in turn] + current
+    if summary and used + message_tokens(summary) <= token_budget:
+        result.insert(0, summary)
+    logging.info(
+        json.dumps(
+            {
+                "event": "context_budget",
+                "budget_tokens": token_budget,
+                "estimated_tokens": cost(result),
+                "input_messages": len(messages),
+                "output_messages": len(result),
+                "dropped_turns": len(dropped),
+                "summary_included": bool(
+                    result and isinstance(result[0], SystemMessage)
+                ),
+            }
+        )
+    )
+    return result
+
+
+def build_context(
+    messages: list[BaseMessage], system_prompt: str, tool_schemas: list[dict]
+) -> list[BaseMessage]:
+    limit = min(
+        PROMPT_BUDGET_TOKENS,
+        CONTEXT_WINDOW_TOKENS - RESPONSE_RESERVE_TOKENS - SAFETY_RESERVE_TOKENS,
+    )
+    system = SystemMessage(content=system_prompt)
+    budget = limit - message_tokens(system) - estimate_tokens(tool_schemas)
+    if budget <= 0:
+        raise ValueError(
+            "System instructions and tool definitions exceed the configured prompt budget."
+        )
+    history = trim_history(messages, token_budget=budget)
+    logging.info(
+        json.dumps(
+            {
+                "event": "prompt_budget",
+                "limit_tokens": limit,
+                "system_tokens": message_tokens(system),
+                "tool_schema_tokens": estimate_tokens(tool_schemas),
+                "estimated_prompt_tokens": message_tokens(system)
+                + estimate_tokens(tool_schemas)
+                + sum(message_tokens(m) for m in history),
+                "response_reserve_tokens": RESPONSE_RESERVE_TOKENS,
+            }
+        )
+    )
+    return [system] + history
diff --git a/blueprints/conversation/memory.py b/blueprints/conversation/memory.py
index 5db37b5..06d4656 100644
--- a/blueprints/conversation/memory.py
+++ b/blueprints/conversation/memory.py
@@ -1,5 +1,8 @@
 from .models import UserMemory
 from .prompts import SIMBA_SYSTEM_PROMPT
+from .context import estimate_tokens
+
+MEMORY_BUDGET_TOKENS = 1000
 
 
 async def get_memories_for_user(user_id: str) -> list[str]:
@@ -12,7 +15,16 @@ async def build_system_prompt_with_memories(user_id: str) -> str:
     memories = await get_memories_for_user(user_id)
     if not memories:
         return SIMBA_SYSTEM_PROMPT
-    block = "\n".join(f"- {m}" for m in memories)
+    selected = []
+    used = 0
+    for memory in memories:
+        cost = estimate_tokens(f"- {memory}\n")
+        if used + cost <= MEMORY_BUDGET_TOKENS:
+            selected.append(memory)
+            used += cost
+    block = "\n".join(f"- {m}" for m in selected)
+    if len(selected) < len(memories):
+        block += "\n[Additional saved memories omitted from this prompt.]"
     return f"{SIMBA_SYSTEM_PROMPT}\n\nUSER MEMORIES (facts the user has asked you to remember):\n{block}"
 
 
diff --git a/blueprints/ynab/tools.py b/blueprints/ynab/tools.py
index c2272bc..469b5d4 100644
--- a/blueprints/ynab/tools.py
+++ b/blueprints/ynab/tools.py
@@ -14,6 +14,13 @@ from zoneinfo import ZoneInfo
 from langchain.tools import tool
 from tortoise import connections
 
+from blueprints.conversation.artifacts_util import (
+    format_date_range,
+    format_month,
+    json_safe,
+    make_artifact,
+)
+
 from .sync import ensure_fresh
 
 logger = logging.getLogger(__name__)
@@ -23,6 +30,8 @@ NOT_SYNCED = "YNAB data is unavailable: the budget has not been synced yet."
 # Keep in step with TOOL_RESULT_MAX_CHARS in blueprints/conversation/logic.py;
 # longer results get truncated there anyway and crowd the 32k context.
 MAX_TRANSACTIONS = 40
+# Rows in the ynab.transactions artifact (the side panel, not the LLM)
+ARTIFACT_MAX_TRANSACTIONS = 500
 
 # ynab_recent_changes accepts the names it prints as well as stored types
 ENTITY_TYPE_ALIASES = {
@@ -64,6 +73,19 @@ def ynab_tool_errors(fn):
     return wrapper
 
 
+def ynab_artifact_tool(fn):
+    """For content_and_artifact tools: errors become (text, None), and bare
+    strings (not-synced, bad input, empty results) get no artifact."""
+    wrapped = ynab_tool_errors(fn)
+
+    @functools.wraps(fn)
+    async def wrapper(*args, **kwargs):
+        result = await wrapped(*args, **kwargs)
+        return (result, None) if isinstance(result, str) else result
+
+    return wrapper
+
+
 # Every transaction line, with split transactions expanded into their
 # subtransactions so category/payee filters see the real allocation.
 LINES_CTE = """
@@ -114,6 +136,11 @@ def _usd(value: Decimal | float | None) -> str:
     return f"{sign}${abs(value):,.2f}"
 
 
+def _amount(value: Decimal | float | None) -> float:
+    """Dollar amount for artifacts (JSON has no Decimal)."""
+    return float(value or 0)
+
+
 def _parse_date(value: str, default: date | None) -> date | None:
     return date.fromisoformat(value) if value else default
 
@@ -128,9 +155,9 @@ async def _query(sql: str, *params) -> list[dict]:
     return await connections.get("default").execute_query_dict(sql, list(params))
 
 
-@tool
-@ynab_tool_errors
-async def ynab_budget_summary(month: str = "") -> str:
+@tool(response_format="content_and_artifact")
+@ynab_artifact_tool
+async def ynab_budget_summary(month: str = ""):
     """Get YNAB budget overview for a month: Ready to Assign, income, assigned, spent, age of money, overspent categories, and net worth.
 
     Args:
@@ -191,12 +218,29 @@ async def ynab_budget_summary(month: str = "") -> str:
         )
     else:
         lines.append("No overspent categories.")
+    net_worth = sum(by_budget.values(), Decimal(0))
     lines.append(
-        f"Net worth: {_usd(sum(by_budget.values(), Decimal(0)))} "
+        f"Net worth: {_usd(net_worth)} "
         f"(budget accounts {_usd(by_budget.get(True))}, "
         f"tracking accounts {_usd(by_budget.get(False))})"
     )
-    return "\n".join(lines)
+    data = {
+        "month": f"{start:%Y-%m}",
+        "ready_to_assign": _amount(m["to_be_budgeted"]),
+        "income": _amount(m["income"]),
+        "assigned": _amount(m["budgeted"]),
+        "spent": _amount(spent[0]["spent"]),
+        "net_worth": _amount(net_worth),
+        "overspent": [
+            {"name": r["name"], "available": _amount(r["balance"])} for r in overspent
+        ],
+    }
+    if m["age_of_money"] is not None:
+        data["age_of_money"] = m["age_of_money"]
+    artifact = make_artifact(
+        "ynab.summary", f"Budget · {format_month(data['month'])}", json_safe(data)
+    )
+    return "\n".join(lines), artifact
 
 
 @tool
@@ -230,8 +274,8 @@ async def ynab_account_balances(include_closed: bool = False) -> str:
     return "\n".join(lines) + f"\n\nNet worth (open accounts): {_usd(total)}"
 
 
-@tool
-@ynab_tool_errors
+@tool(response_format="content_and_artifact")
+@ynab_artifact_tool
 async def ynab_search_transactions(
     start_date: str = "",
     end_date: str = "",
@@ -242,7 +286,7 @@ async def ynab_search_transactions(
     min_amount: float = 0,
     max_amount: float = 0,
     limit: int = 20,
-) -> str:
+):
     """Search YNAB transactions. Split transactions are expanded into their category lines.
 
     Args:
@@ -305,12 +349,16 @@ async def ynab_search_transactions(
         return f"No transactions found from {range_text}."
 
     limit = min(max(1, limit), MAX_TRANSACTIONS)
-    rows = await _query(
+    # One query feeds both the text (first `limit` rows) and the artifact; the
+    # id tie-break keeps the order stable regardless of LIMIT.
+    all_rows = await _query(
         f"""{LINES_CTE}
             SELECT * FROM lines l WHERE {where}
-            ORDER BY l.date DESC, abs(l.amount) DESC LIMIT {limit}""",
+            ORDER BY l.date DESC, abs(l.amount) DESC, l.id
+            LIMIT {ARTIFACT_MAX_TRANSACTIONS}""",
         *params,
     )
+    rows = all_rows[:limit]
     lines = [
         f"Found {count} transactions from {range_text}. "
         f"Outflows {_usd(totals[0]['outflow'])}, inflows {_usd(totals[0]['inflow'])}."
@@ -327,11 +375,38 @@ async def ynab_search_transactions(
         lines.append(line)
     if count > len(rows):
         lines.append(f"(Showing {len(rows)} most recent of {count})")
-    return "\n".join(lines)
+
+    transactions = []
+    for r in all_rows:
+        txn = {
+            "date": r["date"],
+            "payee": r["payee_name"] or "Unknown payee",
+            "category": r["category_name"] or "Uncategorized",
+            "account": r["account_name"],
+            "amount": _amount(r["amount"]),
+        }
+        if r["memo"]:
+            txn["memo"] = r["memo"]
+        transactions.append(txn)
+    title_range = format_date_range(str(start), str(end)) if start else f"through {end}"
+    artifact = make_artifact(
+        "ynab.transactions",
+        f"Transactions · {title_range}",
+        json_safe(
+            {
+                "start_date": start,
+                "end_date": end,
+                "count": count,
+                "total": _amount(totals[0]["outflow"] + totals[0]["inflow"]),
+                "transactions": transactions,
+            }
+        ),
+    )
+    return "\n".join(lines), artifact
 
 
-@tool
-@ynab_tool_errors
+@tool(response_format="content_and_artifact")
+@ynab_artifact_tool
 async def ynab_spending_report(
     group_by: str = "category",
     start_date: str = "",
@@ -339,7 +414,7 @@ async def ynab_spending_report(
     category: str = "",
     payee: str = "",
     top: int = 15,
-) -> str:
+):
     """Total YNAB spending grouped by category, category_group, payee, account, or month. Use group_by='month' for trends over time.
 
     Args:
@@ -377,7 +452,7 @@ async def ynab_spending_report(
             JOIN ynab_accounts a ON a.id = l.account_id
             LEFT JOIN ynab_categories c ON c.id = l.category_id
             LEFT JOIN ynab_category_groups g ON g.id = c.category_group_id
-            WHERE {' AND '.join(conditions)}
+            WHERE {" AND ".join(conditions)}
             GROUP BY 1 ORDER BY {order}""",
         *params,
     )
@@ -392,7 +467,7 @@ async def ynab_spending_report(
             FROM lines l
             JOIN ynab_accounts a ON a.id = l.account_id
             LEFT JOIN ynab_categories c ON c.id = l.category_id
-            WHERE {' AND '.join(conditions)}""",
+            WHERE {" AND ".join(conditions)}""",
         *params,
     )
     outflows, inflows = totals[0]["outflows"], totals[0]["inflows"]
@@ -409,12 +484,29 @@ async def ynab_spending_report(
         lines.append(f"- {len(rows) - len(shown)} others: {_usd(rest)}")
     if group_by == "month" and len(rows) > 1:
         lines.append(f"Monthly average: {_usd(outflows / len(rows))}")
-    return "\n".join(lines)
+    artifact = make_artifact(
+        "ynab.spending_report",
+        f"Spending by {group_by.replace('_', ' ')} · "
+        f"{format_date_range(str(start), str(end))}",
+        json_safe(
+            {
+                "start_date": start,
+                "end_date": end,
+                "group_by": group_by,
+                "rows": [
+                    {"key": r["key"], "amount": _amount(r["spent"]), "count": r["n"]}
+                    for r in rows
+                ],
+                "total": _amount(outflows),
+            }
+        ),
+    )
+    return "\n".join(lines), artifact
 
 
-@tool
-@ynab_tool_errors
-async def ynab_category_budget(month: str = "", category_group: str = "") -> str:
+@tool(response_format="content_and_artifact")
+@ynab_artifact_tool
+async def ynab_category_budget(month: str = "", category_group: str = ""):
     """Get YNAB categories for a month grouped by category group: assigned, activity (negative = spent), available, and goal target. Flags overspending.
 
     Args:
@@ -447,12 +539,23 @@ async def ynab_category_budget(month: str = "", category_group: str = "") -> str
 
     lines = [f"Categories for {start:%Y-%m}:"]
     current = None
+    groups = []
     for r in rows:
         if not (r["budgeted"] or r["activity"] or r["balance"]):
             continue
         if r["group_name"] != current:
             current = r["group_name"]
             lines.append(f"\n{current}")
+            groups.append({"name": current, "categories": []})
+        category = {
+            "name": r["name"],
+            "assigned": _amount(r["budgeted"]),
+            "activity": _amount(r["activity"]),
+            "available": _amount(r["balance"]),
+        }
+        if r["goal_target"]:
+            category["goal_target"] = _amount(r["goal_target"])
+        groups[-1]["categories"].append(category)
         line = (
             f"  {r['name']}: assigned {_usd(r['budgeted'])}, "
             f"activity {_usd(r['activity'])}, available {_usd(r['balance'])}"
@@ -462,7 +565,14 @@ async def ynab_category_budget(month: str = "", category_group: str = "") -> str
         if r["balance"] < 0:
             line += " [OVERSPENT]"
         lines.append(line)
-    return "\n".join(lines)
+    artifact = None
+    if groups:
+        artifact = make_artifact(
+            "ynab.category_budget",
+            f"Category budget · {format_month(f'{start:%Y-%m}')}",
+            json_safe({"month": f"{start:%Y-%m}", "groups": groups}),
+        )
+    return "\n".join(lines), artifact
 
 
 @tool
diff --git a/desktop/src-tauri/src/lib.rs b/desktop/src-tauri/src/lib.rs
index 79d5e4a..8c10adc 100644
--- a/desktop/src-tauri/src/lib.rs
+++ b/desktop/src-tauri/src/lib.rs
@@ -146,6 +146,8 @@ pub fn run() {
                 .title("Simba")
                 .inner_size(1200.0, 820.0)
                 .min_inner_size(420.0, 520.0)
+                // Let HTML5 drag-and-drop reach the webview (file drop in chat).
+                .disable_drag_drop_handler()
                 .build()?;
             build_tray(app.handle())?;
             register_hotkey(app.handle())?;
diff --git a/docker-compose.yml b/docker-compose.yml
index ff46df1..59bde2f 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -27,6 +27,7 @@ x-raggr-common: &raggr-common
     - YNAB_SYNC_INTERVAL=${YNAB_SYNC_INTERVAL:-900}
     - MEALIE_BASE_URL=${MEALIE_BASE_URL}
     - MEALIE_API_TOKEN=${MEALIE_API_TOKEN}
+    - MEALIE_GROUP_SLUG=${MEALIE_GROUP_SLUG:-home}
     - TWILIO_ACCOUNT_SID=${TWILIO_ACCOUNT_SID}
     - TWILIO_AUTH_TOKEN=${TWILIO_AUTH_TOKEN}
     - TWILIO_WHATSAPP_NUMBER=${TWILIO_WHATSAPP_NUMBER}
@@ -40,6 +41,7 @@ x-raggr-common: &raggr-common
     - OBSIDIAN_DEVICE_NAME=${OBSIDIAN_DEVICE_NAME}
     - OBSIDIAN_CONTINUOUS_SYNC=${OBSIDIAN_CONTINUOUS_SYNC:-false}
     - OBSIDIAN_VAULT_PATH=${OBSIDIAN_VAULT_PATH:-/app/data/obsidian}
+    - OBSIDIAN_VAULT_NAME=${OBSIDIAN_VAULT_NAME:-}
     - S3_ENDPOINT_URL=${S3_ENDPOINT_URL}
     - S3_ACCESS_KEY_ID=${S3_ACCESS_KEY_ID}
     - S3_SECRET_ACCESS_KEY=${S3_SECRET_ACCESS_KEY}
diff --git a/docs/context-management.md b/docs/context-management.md
new file mode 100644
index 0000000..9a60960
--- /dev/null
+++ b/docs/context-management.md
@@ -0,0 +1,43 @@
+# Conversation context management
+
+The LangGraph checkpoint retains original messages and artifacts. Each model
+call constructs a bounded view; compaction never rewrites the checkpoint.
+
+The prompt budget includes system instructions, saved memories, tool schemas
+(including admin tools), message content and tool arguments. The default target
+is 16,000 estimated tokens. A 4,096-token generation limit and 2,048-token safety
+reserve also constrain the budget against the configured 32,768-token window.
+
+Estimates use UTF-8 bytes divided by three, message overhead, and a fixed image
+allowance. These are estimates rather than model-specific tokenizer counts.
+Compare `prompt_budget.estimated_prompt_tokens` with actual `stream_request`
+model-call usage and adjust the target/window for the deployed backend.
+
+The current user request is always retained. Oversized tool results become
+marked excerpts preserving their beginning and end; all tool IDs and arguments
+remain. If necessary, intermediate assistant text is also shortened. If the
+mandatory request and exchange structure cannot fit, the request fails with an
+explicit error rather than silently dropping the question.
+
+Recent history is selected as complete turns. Older user messages, assistant
+answers and tool results are capped; earlier images become placeholders.
+Incomplete tool exchanges from cancelled calls and orphan results are removed
+from the prompt. A small budget is reserved for bounded question/answer excerpts
+from older turns. These excerpts are not an LLM-generated rolling summary and do
+not guarantee retention of every historical decision. No extra model call is
+added to the request path. Saved memories use a separate 1,000-token estimated
+budget, preferring recent entries without deleting omitted memories.
+
+Obsidian reads accept `start_line` (one-based content line, excluding frontmatter)
+and `max_lines`, allowing focused follow-up reads. Full artifact content remains
+available to the interface and checkpoint.
+
+Configuration:
+
+- `CONTEXT_WINDOW_TOKENS`: smallest supported context window across backends.
+- `PROMPT_BUDGET_TOKENS`: prompt target, including fixed instructions and tools.
+- `RESPONSE_RESERVE_TOKENS`: maximum generated tokens and reserved answer space.
+
+`context_budget` logs history estimates, message counts, dropped turns and excerpt
+inclusion. `prompt_budget` logs fixed overhead and the complete prompt estimate.
+Neither log includes message content.
diff --git a/raggr-frontend/src/App.css b/raggr-frontend/src/App.css
index 9670d2e..6f368e7 100644
--- a/raggr-frontend/src/App.css
+++ b/raggr-frontend/src/App.css
@@ -202,3 +202,11 @@ body {
   box-shadow: 0 1px 3px rgba(0,0,0,0.15);
 }
 .toggle-track.checked .toggle-thumb { transform: translateX(16px); }
+
+@keyframes sheet-in {
+  from { transform: translateY(100%); }
+  to   { transform: translateY(0); }
+}
+.animate-sheet-in {
+  animation: sheet-in 0.25s ease-out;
+}
diff --git a/raggr-frontend/src/api/artifactService.ts b/raggr-frontend/src/api/artifactService.ts
new file mode 100644
index 0000000..3d2c707
--- /dev/null
+++ b/raggr-frontend/src/api/artifactService.ts
@@ -0,0 +1,36 @@
+import { userService } from "./userService";
+import type { Artifact, ArtifactRef } from "./artifactTypes";
+
+/** A list entry from `GET /api/artifacts`: the ref plus where it came from. */
+export type ArtifactListItem = ArtifactRef & {
+  tool: string;
+  message_id: string | null;
+  created_at: string;
+};
+
+class ArtifactService {
+  private baseUrl = "/api/artifacts";
+
+  async listArtifacts(conversationId: string): Promise<ArtifactListItem[]> {
+    const qs = new URLSearchParams({ conversation_id: conversationId });
+    const response = await userService.fetchWithAuth(`${this.baseUrl}?${qs}`);
+    if (!response.ok) {
+      throw new Error("Failed to list artifacts");
+    }
+    return await response.json();
+  }
+
+  async getArtifact(id: string): Promise<Artifact> {
+    const response = await userService.fetchWithAuth(
+      `${this.baseUrl}/${encodeURIComponent(id)}`,
+    );
+    if (!response.ok) {
+      throw new Error(
+        response.status === 404 ? "Artifact not found" : "Failed to load artifact",
+      );
+    }
+    return await response.json();
+  }
+}
+
+export const artifactService = new ArtifactService();
diff --git a/raggr-frontend/src/api/artifactTypes.ts b/raggr-frontend/src/api/artifactTypes.ts
new file mode 100644
index 0000000..b3db843
--- /dev/null
+++ b/raggr-frontend/src/api/artifactTypes.ts
@@ -0,0 +1,37 @@
+// Artifact types shared by the activity timeline and the artifact panel.
+// Shapes follow the contract in docs/cowork-ui-plan.md.
+
+export type ArtifactKind =
+  | "mealie.recipe"
+  | "mealie.meal_plan"
+  | "mealie.shopping_lists"
+  | "obsidian.note"
+  | "search.documents"
+  | "ynab.summary"
+  | "ynab.transactions"
+  | "ynab.spending_report"
+  | "ynab.category_budget";
+
+/** Lightweight reference carried by `tool_end` events and tool messages. */
+export type ArtifactRef = {
+  id: string;
+  kind: ArtifactKind;
+  title: string;
+};
+
+export type ArtifactSourceRef = {
+  system: "mealie" | "obsidian" | "paperless" | "ynab" | "web";
+  id?: string;
+  path?: string;
+  url?: string;
+};
+
+/** Full artifact as returned by `GET /api/artifacts/<id>`. */
+export type Artifact = ArtifactRef & {
+  data: object;
+  source_ref: ArtifactSourceRef | null;
+  tool: string;
+  conversation_id: string;
+  message_id: string | null;
+  created_at: string;
+};
diff --git a/raggr-frontend/src/api/conversationService.ts b/raggr-frontend/src/api/conversationService.ts
index 66bbc98..d47cacb 100644
--- a/raggr-frontend/src/api/conversationService.ts
+++ b/raggr-frontend/src/api/conversationService.ts
@@ -1,10 +1,29 @@
 import { userService } from "./userService";
+import type { ArtifactRef } from "./artifactTypes";
+
+export type ToolInput = Record<string, string | number | boolean>;
 
 export type SSEEvent =
   | { type: "thinking" }
   | { type: "thinking_delta"; delta: string }
-  | { type: "tool_start"; tool: string }
-  | { type: "tool_end"; tool: string }
+  // v2 servers send run_id/label/input and run_id/label/status/ms/artifact;
+  // older servers send only `tool`, so everything else is optional here.
+  | {
+      type: "tool_start";
+      tool: string;
+      run_id?: string;
+      label?: string;
+      input?: ToolInput;
+    }
+  | {
+      type: "tool_end";
+      tool: string;
+      run_id?: string;
+      label?: string;
+      status?: "ok" | "error";
+      ms?: number;
+      artifact?: ArtifactRef | null;
+    }
   | { type: "content"; delta: string }
   | { type: "response"; message: string }
   | { type: "error"; message: string; stalled?: boolean };
@@ -17,6 +36,10 @@ interface Message {
   speaker: "user" | "simba" | "tool";
   created_at: string;
   image_key?: string | null;
+  // Tool messages only (v2 servers).
+  tool?: string;
+  label?: string;
+  artifact?: ArtifactRef | null;
 }
 
 interface Conversation {
@@ -28,6 +51,12 @@ interface Conversation {
   user_id?: string;
 }
 
+export type UploadResult =
+  | { kind: "image"; image_key: string }
+  | { kind: "file"; file_key: string; name: string; chars: number };
+
+export class UploadError extends Error {}
+
 interface QueryResponse {
   response: string;
 }
@@ -159,16 +188,16 @@ class ConversationService {
     return await response.json();
   }
 
-  async uploadImage(
+  async uploadAttachment(
     file: File,
     conversationId: string,
-  ): Promise<{ image_key: string }> {
+  ): Promise<UploadResult> {
     const formData = new FormData();
     formData.append("file", file);
     formData.append("conversation_id", conversationId);
 
     const response = await userService.fetchWithAuth(
-      `${this.conversationBaseUrl}/upload-image`,
+      `${this.conversationBaseUrl}/upload`,
       {
         method: "POST",
         body: formData,
@@ -177,8 +206,8 @@ class ConversationService {
     );
 
     if (!response.ok) {
-      const data = await response.json();
-      throw new Error(data.error || "Failed to upload image");
+      const data = await response.json().catch(() => ({}));
+      throw new UploadError(data.error || "Failed to upload file");
     }
 
     return await response.json();
@@ -201,11 +230,15 @@ class ConversationService {
     onEvent: SSEEventCallback,
     signal?: AbortSignal,
     imageKey?: string,
+    fileKey?: string,
   ): Promise<void> {
     const body: Record<string, string> = { query, conversation_id };
     if (imageKey) {
       body.image_key = imageKey;
     }
+    if (fileKey) {
+      body.file_key = fileKey;
+    }
 
     const response = await userService.fetchWithAuth(
       `${this.conversationBaseUrl}/stream-query`,
diff --git a/raggr-frontend/src/components/ActivityTimeline.tsx b/raggr-frontend/src/components/ActivityTimeline.tsx
new file mode 100644
index 0000000..1734fa6
--- /dev/null
+++ b/raggr-frontend/src/components/ActivityTimeline.tsx
@@ -0,0 +1,242 @@
+import React, { useEffect, useId, useState } from "react";
+import {
+  BookOpen,
+  CalendarDays,
+  Cat,
+  Check,
+  ChefHat,
+  ChevronDown,
+  Clock,
+  Globe,
+  Library,
+  LoaderCircle,
+  Mail,
+  NotebookPen,
+  Package,
+  PanelRightOpen,
+  PawPrint,
+  Utensils,
+  Wallet,
+  Wrench,
+  X,
+  type LucideIcon,
+} from "lucide-react";
+import { cn } from "../lib/utils";
+import type { ArtifactRef } from "../api/artifactTypes";
+import type { ToolInput } from "../api/conversationService";
+import type { ToolMessage } from "../hooks/useChat";
+
+// Checked in order, so longer prefixes (simbakit_) come before shorter ones.
+const TOOL_ICONS: [prefix: string, icon: LucideIcon][] = [
+  ["mealie", ChefHat],
+  ["ynab", Wallet],
+  ["obsidian", NotebookPen],
+  ["journal", BookOpen],
+  ["simbakit", PawPrint],
+  ["simba_search", Cat],
+  ["web_search", Globe],
+  ["homebox", Package],
+  ["bookstack", Library],
+  ["gmail", Mail],
+  ["beli", Utensils],
+  ["get_current_date", Clock],
+];
+
+// Calendar tools are verb-first (get_calendar_events, create_calendar_event),
+// so they match anywhere in the name rather than by prefix.
+const iconFor = (tool: string): LucideIcon =>
+  tool.includes("calendar")
+    ? CalendarDays
+    : (TOOL_ICONS.find(([prefix]) => tool.startsWith(prefix))?.[1] ?? Wrench);
+
+const MAX_VALUE_CHARS = 40;
+
+/** `month: 2026-10 · group_by: category`, with long values clipped. */
+export const summariseInput = (input?: ToolInput): string =>
+  Object.entries(input ?? {})
+    .filter(([, value]) => value !== "" && value !== null && value !== undefined)
+    .map(([key, value]) => {
+      const text = String(value).replace(/\s+/g, " ");
+      return `${key}: ${text.length > MAX_VALUE_CHARS ? `${text.slice(0, MAX_VALUE_CHARS)}…` : text}`;
+    })
+    .join(" · ");
+
+export const formatDuration = (ms: number): string =>
+  ms < 1000 ? `${Math.round(ms)} ms` : `${(ms / 1000).toFixed(1)} s`;
+
+/**
+ * Wall-clock span of the block when the client timed it (parallel calls
+ * overlap, so summing would overcount); otherwise the sum of server
+ * durations. Restored conversations have neither.
+ */
+const totalDuration = (rows: ToolMessage[]): number | null => {
+  const starts = rows.map((r) => r.startedAt);
+  const ends = rows.map((r) => r.endedAt);
+  if (starts.every((t) => t != null) && ends.every((t) => t != null)) {
+    return Math.max(...(ends as number[])) - Math.min(...(starts as number[]));
+  }
+  const timed = rows.filter((r) => r.ms != null);
+  return timed.length ? timed.reduce((sum, r) => sum + (r.ms ?? 0), 0) : null;
+};
+
+type ActivityTimelineProps = {
+  rows: ToolMessage[];
+  /** True while this block belongs to the in-flight turn. */
+  active: boolean;
+  onOpenArtifact: (ref: ArtifactRef) => void;
+};
+
+export const ActivityTimeline = React.memo(
+  ({ rows, active, onOpenArtifact }: ActivityTimelineProps) => {
+    const working = active || rows.some((r) => r.status === "running");
+    // null = follow the turn (open while working, collapsed when done).
+    const [userExpanded, setUserExpanded] = useState<boolean | null>(null);
+    const listId = useId();
+
+    // Collapse once the turn finishes, even if the user toggled mid-run.
+    useEffect(() => {
+      if (!working) setUserExpanded(null);
+    }, [working]);
+
+    const expanded = userExpanded ?? working;
+    const failed = rows.filter((r) => r.status === "error").length;
+    const total = totalDuration(rows);
+
+    const summary = [
+      "Simba worked",
+      `${rows.length} ${rows.length === 1 ? "step" : "steps"}`,
+      total != null ? formatDuration(total) : null,
+      failed ? `${failed} failed` : null,
+    ]
+      .filter(Boolean)
+      .join(" · ");
+
+    return (
+      <div className="flex justify-center message-enter">
+        <div className="w-full max-w-2xl">
+          <button
+            type="button"
+            onClick={() => setUserExpanded(!expanded)}
+            aria-expanded={expanded}
+            aria-controls={listId}
+            className={cn(
+              "w-full flex items-center justify-between gap-2",
+              "px-3 py-1.5 rounded-xl",
+              "bg-leaf-pale border border-leaf-light/50",
+              "text-xs text-leaf-dark",
+              "hover:bg-leaf-light/20 transition-colors cursor-pointer",
+            )}
+          >
+            <span className="flex items-center gap-1.5 min-w-0">
+              {working ? (
+                <LoaderCircle size={13} className="animate-spin shrink-0" />
+              ) : failed ? (
+                <X size={13} className="text-red-500 shrink-0" />
+              ) : (
+                <Check size={13} className="shrink-0" />
+              )}
+              <span className={cn("truncate", working && "italic")}>
+                {working ? "Simba is working…" : summary}
+              </span>
+            </span>
+            <ChevronDown
+              size={13}
+              className={cn(
+                "text-leaf-dark/60 transition-transform duration-200 shrink-0",
+                expanded && "rotate-180",
+              )}
+            />
+          </button>
+
+          {expanded && (
+            <ul
+              id={listId}
+              className={cn(
+                "mt-1 rounded-xl overflow-hidden",
+                "bg-warm-white border border-sand-light",
+                "divide-y divide-sand-light/60",
+              )}
+            >
+              {rows.map((row) => (
+                <TimelineRow
+                  key={row.run_id}
+                  row={row}
+                  onOpenArtifact={onOpenArtifact}
+                />
+              ))}
+            </ul>
+          )}
+        </div>
+      </div>
+    );
+  },
+);
+
+const TimelineRow = ({
+  row,
+  onOpenArtifact,
+}: {
+  row: ToolMessage;
+  onOpenArtifact: (ref: ArtifactRef) => void;
+}) => {
+  const Icon = iconFor(row.tool);
+  const inputSummary = summariseInput(row.input);
+  const artifact = row.artifact;
+
+  return (
+    <li className="flex items-center gap-2.5 px-3 py-2">
+      <span
+        className="w-6 h-6 shrink-0 rounded-lg bg-leaf-pale text-leaf-dark flex items-center justify-center"
+        title={row.tool}
+      >
+        <Icon size={13} />
+      </span>
+
+      <div className="min-w-0 flex-1">
+        <div className="text-[13px] text-charcoal truncate">{row.label}</div>
+        {inputSummary && (
+          <div
+            className="text-[11px] text-warm-gray font-mono truncate"
+            title={inputSummary}
+          >
+            {inputSummary}
+          </div>
+        )}
+      </div>
+
+      {artifact && (
+        <button
+          type="button"
+          onClick={() => onOpenArtifact(artifact)}
+          title={artifact.title}
+          aria-label={`Open ${artifact.title}`}
+          className={cn(
+            "shrink-0 inline-flex items-center gap-1 px-2 py-0.5 rounded-full",
+            "bg-amber-pale border border-amber-soft/70 text-[11px] font-medium text-amber-dark",
+            "hover:bg-amber-soft/40 transition-colors cursor-pointer",
+          )}
+        >
+          <PanelRightOpen size={11} />
+          Open
+        </button>
+      )}
+
+      <span className="shrink-0 flex items-center gap-1.5 text-[11px] text-warm-gray tabular-nums">
+        {row.ms != null && row.status !== "running" && (
+          <span>{formatDuration(row.ms)}</span>
+        )}
+        {row.status === "running" ? (
+          <LoaderCircle
+            size={14}
+            className="animate-spin text-leaf"
+            aria-label="Running"
+          />
+        ) : row.status === "error" ? (
+          <X size={14} className="text-red-500" aria-label="Failed" />
+        ) : (
+          <Check size={14} className="text-leaf" aria-label="Done" />
+        )}
+      </span>
+    </li>
+  );
+};
diff --git a/raggr-frontend/src/components/ChatScreen.tsx b/raggr-frontend/src/components/ChatScreen.tsx
index dbc95d9..05add45 100644
--- a/raggr-frontend/src/components/ChatScreen.tsx
+++ b/raggr-frontend/src/components/ChatScreen.tsx
@@ -1,17 +1,21 @@
 import React, { useCallback, useState, useRef } from "react";
-import { useNavigate } from "react-router-dom";
-import { PanelLeftOpen, Menu, X } from "lucide-react";
+import { useMatch, useNavigate } from "react-router-dom";
+import { Library, PanelLeftOpen, Menu, X } from "lucide-react";
 import { QuestionBubble } from "./QuestionBubble";
 import { AnswerBubble } from "./AnswerBubble";
-import { ToolBubble } from "./ToolBubble";
+import { ActivityTimeline } from "./ActivityTimeline";
 import { ThinkingBubble } from "./ThinkingBubble";
 import { MessageInput } from "./MessageInput";
+import { DropOverlay } from "./DropOverlay";
 import { SidebarContent } from "./SidebarContent";
 import { AdminPanel } from "./AdminPanel";
 import { ScheduledMessagesPanel } from "./ScheduledMessagesPanel";
+import { ArtifactPanel } from "./artifacts/ArtifactPanel";
+import { AUTO_OPEN_MIN_WIDTH, useArtifactPanel } from "./artifacts/useArtifactPanel";
 import { cn } from "../lib/utils";
 import { useConversations } from "../hooks/useConversations";
-import { useChat } from "../hooks/useChat";
+import { useChat, type ToolMessage } from "../hooks/useChat";
+import type { ArtifactRef } from "../api/artifactTypes";
 import catIcon from "../assets/cat.png";
 
 type ChatScreenProps = {
@@ -50,14 +54,42 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
 
   const onSessionExpired = useCallback(() => setAuthenticated(false), [setAuthenticated]);
 
+  const conversationId = useMatch("/c/:conversationId")?.params.conversationId;
+  const conversationIdRef = useRef(conversationId);
+  conversationIdRef.current = conversationId;
+
+  const artifactPanel = useArtifactPanel(conversationId);
+  // Opens an artifact in the panel; the timeline's "Open" chip calls this.
+  const openArtifact = artifactPanel.open;
+
+  // Auto-open on wide windows; newest wins. Narrower windows rely on the
+  // timeline chip or the header's Artifacts button.
+  const handleArtifact = useCallback(
+    (ref: ArtifactRef, turnConversationId: string) => {
+      if (turnConversationId !== conversationIdRef.current) return;
+      if (window.innerWidth < AUTO_OPEN_MIN_WIDTH) return;
+      openArtifact(ref, { auto: true });
+    },
+    [openArtifact],
+  );
+
+  const toggleArtifacts = useCallback(() => {
+    const p = artifactPanel;
+    if (p.isOpen && (p.view === "library" || !p.active)) p.collapse();
+    else p.showLibrary();
+  }, [artifactPanel]);
+
   const {
     messages,
     isLoading,
     streaming,
     thinking,
     messagesLoading,
-    pendingImage,
-    setPendingImage,
+    pendingAttachment,
+    attachFile,
+    clearAttachment,
+    attachmentError,
+    clearAttachmentError,
     sendMessage,
     stopGeneration,
     error,
@@ -71,6 +103,7 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
     refreshConversations,
     onSessionExpired,
     scrollToBottom,
+    onArtifact: handleArtifact,
   });
 
   // Keep ref in sync for scrollToBottom behavior
@@ -112,9 +145,6 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
     [deleteConversation],
   );
 
-  const handleImageSelect = useCallback((file: File) => setPendingImage(file), [setPendingImage]);
-  const handleClearImage = useCallback(() => setPendingImage(null), [setPendingImage]);
-
   const handleLogout = () => {
     localStorage.removeItem("access_token");
     localStorage.removeItem("refresh_token");
@@ -194,7 +224,8 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
       {showAdminPanel && <AdminPanel onClose={() => setShowAdminPanel(false)} />}
       {showScheduler && <ScheduledMessagesPanel onClose={() => setShowScheduler(false)} />}
 
-      <div className="flex-1 flex flex-col h-full overflow-hidden min-w-0">
+      <div className="relative flex-1 flex flex-col h-full overflow-hidden min-w-0">
+        <DropOverlay onDrop={attachFile} />
         <header className="md:hidden flex items-center justify-between px-4 py-3 bg-warm-white border-b border-sand-light/60">
           <div className="flex items-center gap-2">
             <img src={catIcon} alt="Simba" className="w-12 h-12" />
@@ -205,15 +236,52 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
               asksimba
             </h1>
           </div>
-          <button
-            className="w-8 h-8 rounded-xl flex items-center justify-center text-warm-gray hover:text-charcoal hover:bg-cream-dark transition-all cursor-pointer"
-            onClick={() => setShowConversations(true)}
-            aria-label="Open menu"
-          >
-            <Menu size={16} />
-          </button>
+          <div className="flex items-center gap-1">
+            {conversationId && (
+              <button
+                className="w-8 h-8 rounded-xl flex items-center justify-center text-warm-gray hover:text-charcoal hover:bg-cream-dark transition-all cursor-pointer"
+                onClick={toggleArtifacts}
+                aria-label="Artifacts"
+              >
+                <Library size={16} />
+              </button>
+            )}
+            <button
+              className="w-8 h-8 rounded-xl flex items-center justify-center text-warm-gray hover:text-charcoal hover:bg-cream-dark transition-all cursor-pointer"
+              onClick={() => setShowConversations(true)}
+              aria-label="Open menu"
+            >
+              <Menu size={16} />
+            </button>
+          </div>
         </header>
 
+        {conversationId && (
+          <header className="hidden md:flex items-center justify-between gap-3 px-4 py-2 border-b border-sand-light/40">
+            <h2 className="min-w-0 truncate text-sm font-semibold text-warm-gray">
+              {selectedConversation?.title}
+            </h2>
+            <button
+              onClick={toggleArtifacts}
+              aria-pressed={artifactPanel.isOpen}
+              className={cn(
+                "inline-flex shrink-0 items-center gap-1.5 rounded-xl px-3 py-1.5 text-xs font-semibold transition-all cursor-pointer",
+                artifactPanel.isOpen
+                  ? "bg-leaf-pale text-leaf-dark"
+                  : "text-warm-gray hover:text-charcoal hover:bg-cream-dark",
+              )}
+            >
+              <Library size={14} />
+              Artifacts
+              {artifactPanel.tabs.length > 0 && (
+                <span className="rounded-full bg-leaf/15 px-1.5 text-[10px] text-leaf-dark">
+                  {artifactPanel.tabs.length}
+                </span>
+              )}
+            </button>
+          </header>
+        )}
+
         {messages.length === 0 && !messagesLoading ? (
           <div className="flex-1 flex flex-col items-center justify-center px-4 gap-6">
             <div className="relative">
@@ -236,9 +304,11 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
                 onToggleSimbaMode={handleToggleSimbaMode}
                 isLoading={isLoading}
                 onStop={stopGeneration}
-                pendingImage={pendingImage}
-                onImageSelect={handleImageSelect}
-                onClearImage={handleClearImage}
+                pendingAttachment={pendingAttachment}
+                onAttach={attachFile}
+                onClearAttachment={clearAttachment}
+                attachmentError={attachmentError}
+                onDismissAttachmentError={clearAttachmentError}
                 autoFocus
               />
             </div>
@@ -248,6 +318,29 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
             <div className="flex-1 overflow-y-auto px-4 py-6">
               <div className="max-w-3xl mx-auto flex flex-col gap-6">
                 {messages.map((msg, index) => {
+                  if (msg.speaker === "tool") {
+                    // Consecutive tool calls render as one timeline block,
+                    // emitted at the first row of the run.
+                    if (index > 0 && messages[index - 1].speaker === "tool") {
+                      return null;
+                    }
+                    let end = index;
+                    while (end < messages.length && messages[end].speaker === "tool") {
+                      end++;
+                    }
+                    const rows = messages.slice(index, end) as ToolMessage[];
+                    return (
+                      <ActivityTimeline
+                        key={`tools-${rows[0].run_id}`}
+                        rows={rows}
+                        // The trailing block of an in-flight turn stays
+                        // "working" until the answer starts streaming.
+                        active={isLoading && end === messages.length}
+                        onOpenArtifact={openArtifact}
+                      />
+                    );
+                  }
+
                   // When the model has been thinking and content is now streaming,
                   // render ThinkingBubble just before the streaming simba message
                   // so it appears above the answer rather than below it.
@@ -259,9 +352,7 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
                     msg.speaker === "simba";
 
                   const bubble =
-                    msg.speaker === "tool" ? (
-                      <ToolBubble key={index} text={msg.text} />
-                    ) : msg.speaker === "simba" ? (
+                    msg.speaker === "simba" ? (
                       <AnswerBubble key={index} text={msg.text} />
                     ) : (
                       <QuestionBubble key={index} text={msg.text} image_key={msg.image_key} />
@@ -291,7 +382,12 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
                   />
                 )}
 
-                {((isLoading && !streaming && !thinking) || messagesLoading) && (
+                {/* Placeholder dots, unless the activity timeline already shows progress */}
+                {((isLoading &&
+                  !streaming &&
+                  !thinking &&
+                  messages[messages.length - 1]?.speaker !== "tool") ||
+                  messagesLoading) && (
                   <AnswerBubble text="" loading={true} />
                 )}
 
@@ -339,15 +435,19 @@ export const ChatScreen = ({ setAuthenticated, isAdmin }: ChatScreenProps) => {
                   onToggleSimbaMode={handleToggleSimbaMode}
                   isLoading={isLoading}
                   onStop={stopGeneration}
-                  pendingImage={pendingImage}
-                  onImageSelect={handleImageSelect}
-                  onClearImage={handleClearImage}
+                  pendingAttachment={pendingAttachment}
+                  onAttach={attachFile}
+                  onClearAttachment={clearAttachment}
+                  attachmentError={attachmentError}
+                  onDismissAttachmentError={clearAttachmentError}
                 />
               </div>
             </footer>
           </>
         )}
       </div>
+
+      <ArtifactPanel panel={artifactPanel} conversationId={conversationId} />
     </div>
   );
 };
diff --git a/raggr-frontend/src/components/DropOverlay.tsx b/raggr-frontend/src/components/DropOverlay.tsx
new file mode 100644
index 0000000..3b22971
--- /dev/null
+++ b/raggr-frontend/src/components/DropOverlay.tsx
@@ -0,0 +1,87 @@
+import { useEffect, useRef, useState } from "react";
+import { Paperclip } from "lucide-react";
+
+const hasFiles = (e: DragEvent) =>
+  Array.from(e.dataTransfer?.types ?? []).includes("Files");
+
+type DropOverlayProps = {
+  onDrop: (file: File) => void;
+};
+
+/**
+ * Listens for file drags anywhere in the window and covers its positioned
+ * parent (the chat column, beside the artifact panel) with a "Drop to attach"
+ * target. Below lg the panel is a full-screen sheet, so it covers the window
+ * and sits above the sheet. Drags without files (text, links)
+ * are ignored so they keep their normal behaviour.
+ */
+export const DropOverlay = ({ onDrop }: DropOverlayProps) => {
+  const [active, setActive] = useState(false);
+  // dragenter/dragleave fire for every element crossed; count to know when
+  // the drag has really left the window.
+  const depthRef = useRef(0);
+  const onDropRef = useRef(onDrop);
+  onDropRef.current = onDrop;
+
+  useEffect(() => {
+    const handleEnter = (e: DragEvent) => {
+      if (!hasFiles(e)) return;
+      e.preventDefault();
+      depthRef.current += 1;
+      setActive(true);
+    };
+    const handleOver = (e: DragEvent) => {
+      if (!hasFiles(e)) return;
+      // Required for the drop event to fire (and to stop the browser
+      // navigating to the file).
+      e.preventDefault();
+      if (e.dataTransfer) e.dataTransfer.dropEffect = "copy";
+    };
+    const handleLeave = (e: DragEvent) => {
+      if (!hasFiles(e)) return;
+      depthRef.current = Math.max(0, depthRef.current - 1);
+      if (depthRef.current === 0) setActive(false);
+    };
+    const handleDrop = (e: DragEvent) => {
+      if (!hasFiles(e)) return;
+      e.preventDefault();
+      depthRef.current = 0;
+      setActive(false);
+      const file = e.dataTransfer?.files?.[0];
+      if (file) onDropRef.current(file);
+    };
+
+    window.addEventListener("dragenter", handleEnter);
+    window.addEventListener("dragover", handleOver);
+    window.addEventListener("dragleave", handleLeave);
+    window.addEventListener("drop", handleDrop);
+    return () => {
+      window.removeEventListener("dragenter", handleEnter);
+      window.removeEventListener("dragover", handleOver);
+      window.removeEventListener("dragleave", handleLeave);
+      window.removeEventListener("drop", handleDrop);
+    };
+  }, []);
+
+  if (!active) return null;
+
+  return (
+    <div
+      className="pointer-events-none fixed lg:absolute inset-0 z-[45] flex items-center justify-center bg-cream/80 backdrop-blur-sm p-3 md:p-5"
+      data-testid="drop-overlay"
+    >
+      <div className="w-full h-full rounded-3xl border-2 border-dashed border-amber-glow/50 bg-amber-pale/70 flex flex-col items-center justify-center gap-3 message-enter">
+        <div className="w-14 h-14 rounded-2xl bg-warm-white border border-sand shadow-md shadow-sand/30 text-amber-glow flex items-center justify-center">
+          <Paperclip size={24} />
+        </div>
+        <p
+          className="text-lg font-bold text-charcoal"
+          style={{ fontFamily: "var(--font-display)" }}
+        >
+          Drop to attach
+        </p>
+        <p className="text-xs text-warm-gray">Images, PDF, TXT, MD or CSV · up to 10 MB</p>
+      </div>
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/MessageInput.tsx b/raggr-frontend/src/components/MessageInput.tsx
index 67883e2..2dd2f43 100644
--- a/raggr-frontend/src/components/MessageInput.tsx
+++ b/raggr-frontend/src/components/MessageInput.tsx
@@ -1,6 +1,12 @@
 import React, { useEffect, useMemo, useRef } from "react";
-import { ArrowUp, ImagePlus, Square, X } from "lucide-react";
+import { ArrowUp, FileSpreadsheet, FileText, Paperclip, Square, X } from "lucide-react";
 import { cn } from "../lib/utils";
+import {
+  ATTACHMENT_ACCEPT,
+  attachmentKind,
+  fileExtension,
+  formatBytes,
+} from "../lib/attachments";
 import { Textarea } from "./ui/textarea";
 
 type MessageInputProps = {
@@ -12,9 +18,11 @@ type MessageInputProps = {
   query: string;
   isLoading: boolean;
   onStop: () => void;
-  pendingImage: File | null;
-  onImageSelect: (file: File) => void;
-  onClearImage: () => void;
+  pendingAttachment: File | null;
+  onAttach: (file: File) => void;
+  onClearAttachment: () => void;
+  attachmentError: string | null;
+  onDismissAttachmentError: () => void;
   autoFocus?: boolean;
 };
 
@@ -28,15 +36,23 @@ export const MessageInput = React.memo(
     onToggleSimbaMode,
     isLoading,
     onStop,
-    pendingImage,
-    onImageSelect,
-    onClearImage,
+    pendingAttachment,
+    onAttach,
+    onClearAttachment,
+    attachmentError,
+    onDismissAttachmentError,
     autoFocus,
   }: MessageInputProps) => {
     const fileInputRef = useRef<HTMLInputElement>(null);
     const textareaRef = useRef<HTMLTextAreaElement>(null);
 
-    // Create blob URL once per file, revoke on cleanup
+    const pendingImage =
+      pendingAttachment && attachmentKind(pendingAttachment) === "image"
+        ? pendingAttachment
+        : null;
+    const pendingFile = pendingAttachment && !pendingImage ? pendingAttachment : null;
+
+    // Create blob URL once per image, revoke on cleanup
     const previewUrl = useMemo(
       () => (pendingImage ? URL.createObjectURL(pendingImage) : null),
       [pendingImage],
@@ -59,7 +75,7 @@ export const MessageInput = React.memo(
     const handleFileChange = (e: React.ChangeEvent<HTMLInputElement>) => {
       const file = e.target.files?.[0];
       if (file) {
-        onImageSelect(file);
+        onAttach(file);
       }
       // Reset so the same file can be re-selected
       e.target.value = "";
@@ -69,19 +85,21 @@ export const MessageInput = React.memo(
       if (isLoading) return;
       const items = e.clipboardData?.items;
       if (!items) return;
-      for (const item of items) {
+      for (const item of Array.from(items)) {
         if (item.type.startsWith("image/")) {
           const file = item.getAsFile();
           if (file) {
             e.preventDefault();
-            onImageSelect(file);
+            onAttach(file);
             return;
           }
         }
       }
     };
 
-    const canSend = !isLoading && Boolean(query.trim() || pendingImage);
+    const canSend = !isLoading && Boolean(query.trim() || pendingAttachment);
+    const FileIcon =
+      pendingFile && fileExtension(pendingFile.name) === "csv" ? FileSpreadsheet : FileText;
 
     return (
       <div
@@ -102,7 +120,8 @@ export const MessageInput = React.memo(
               />
               <button
                 type="button"
-                onClick={onClearImage}
+                onClick={onClearAttachment}
+                aria-label="Remove attachment"
                 className="absolute -top-1.5 -right-1.5 w-5 h-5 rounded-full bg-charcoal text-white flex items-center justify-center hover:bg-charcoal/80 transition-colors cursor-pointer"
               >
                 <X size={12} />
@@ -111,6 +130,56 @@ export const MessageInput = React.memo(
           </div>
         )}
 
+        {/* File chip */}
+        {pendingFile && (
+          <div className="px-3 pt-3">
+            <div
+              className="relative inline-flex items-center gap-2.5 max-w-full rounded-xl border border-sand bg-cream pl-2 pr-7 py-2 message-enter"
+              data-testid="attachment-chip"
+            >
+              <div className="w-8 h-8 shrink-0 rounded-lg bg-amber-pale text-amber-dark flex items-center justify-center">
+                <FileIcon size={16} />
+              </div>
+              <div className="min-w-0">
+                <div className="text-xs font-medium text-charcoal truncate max-w-[14rem] sm:max-w-xs">
+                  {pendingFile.name}
+                </div>
+                <div className="text-[11px] text-warm-gray">
+                  {fileExtension(pendingFile.name).toUpperCase() || "File"} ·{" "}
+                  {formatBytes(pendingFile.size)}
+                </div>
+              </div>
+              <button
+                type="button"
+                onClick={onClearAttachment}
+                aria-label="Remove attachment"
+                className="absolute top-1.5 right-1.5 w-5 h-5 rounded-full text-warm-gray flex items-center justify-center hover:text-charcoal hover:bg-cream-dark transition-colors cursor-pointer"
+              >
+                <X size={12} />
+              </button>
+            </div>
+          </div>
+        )}
+
+        {attachmentError && (
+          <div className="px-3 pt-3">
+            <div
+              role="alert"
+              className="inline-flex items-center gap-2 px-3 py-1.5 rounded-full bg-red-50 border border-red-200 text-xs text-red-600 message-enter"
+            >
+              <span>{attachmentError}</span>
+              <button
+                type="button"
+                onClick={onDismissAttachmentError}
+                className="text-red-400 hover:text-red-600 transition-colors cursor-pointer"
+                aria-label="Dismiss error"
+              >
+                <X size={13} />
+              </button>
+            </div>
+          </div>
+        )}
+
         {/* Textarea */}
         <Textarea
           ref={textareaRef}
@@ -128,7 +197,7 @@ export const MessageInput = React.memo(
         <input
           ref={fileInputRef}
           type="file"
-          accept="image/*"
+          accept={ATTACHMENT_ACCEPT}
           onChange={handleFileChange}
           className="hidden"
         />
@@ -150,11 +219,13 @@ export const MessageInput = React.memo(
               </span>
             </button>
 
-            {/* Image attach button */}
+            {/* Attach button */}
             <button
               type="button"
               onClick={() => fileInputRef.current?.click()}
               disabled={isLoading}
+              aria-label="Attach a file"
+              title="Attach an image, PDF, TXT, MD or CSV"
               className={cn(
                 "w-7 h-7 rounded-lg flex items-center justify-center transition-all cursor-pointer",
                 isLoading
@@ -162,7 +233,7 @@ export const MessageInput = React.memo(
                   : "text-warm-gray hover:text-charcoal hover:bg-cream-dark",
               )}
             >
-              <ImagePlus size={16} />
+              <Paperclip size={16} />
             </button>
           </div>
 
diff --git a/raggr-frontend/src/components/QuestionBubble.tsx b/raggr-frontend/src/components/QuestionBubble.tsx
index fc90973..666a3ce 100644
--- a/raggr-frontend/src/components/QuestionBubble.tsx
+++ b/raggr-frontend/src/components/QuestionBubble.tsx
@@ -1,5 +1,7 @@
 import React from "react";
+import { FileSpreadsheet, FileText } from "lucide-react";
 import { cn } from "../lib/utils";
+import { fileExtension, splitAttachedFile } from "../lib/attachments";
 import { usePresignedUrl } from "../hooks/usePresignedUrl";
 
 type QuestionBubbleProps = {
@@ -9,6 +11,8 @@ type QuestionBubbleProps = {
 
 export const QuestionBubble = React.memo(({ text, image_key }: QuestionBubbleProps) => {
   const { imageUrl, imageError } = usePresignedUrl(image_key);
+  const { body, fileName } = splitAttachedFile(text);
+  const FileIcon = fileName && fileExtension(fileName) === "csv" ? FileSpreadsheet : FileText;
 
   return (
     <div className="flex justify-end message-enter">
@@ -32,7 +36,21 @@ export const QuestionBubble = React.memo(({ text, image_key }: QuestionBubblePro
             className="max-w-full rounded-xl mb-2"
           />
         )}
-        {text}
+        {fileName && (
+          <div
+            className={cn(
+              "flex items-center gap-1.5 w-fit max-w-full rounded-lg",
+              "bg-warm-white/70 border border-leaf-light/70 px-2 py-1",
+              "text-xs text-leaf-dark",
+              body && "mb-2",
+            )}
+            data-testid="message-attachment"
+          >
+            <FileIcon size={13} className="shrink-0" />
+            <span className="truncate">{fileName}</span>
+          </div>
+        )}
+        {body}
       </div>
     </div>
   );
diff --git a/raggr-frontend/src/components/ToolBubble.tsx b/raggr-frontend/src/components/ToolBubble.tsx
deleted file mode 100644
index 213ef47..0000000
--- a/raggr-frontend/src/components/ToolBubble.tsx
+++ /dev/null
@@ -1,19 +0,0 @@
-import React from "react";
-import { cn } from "../lib/utils";
-
-export const ToolBubble = React.memo(
-  ({ text, pulse = false }: { text: string; pulse?: boolean }) => (
-    <div className="flex justify-center message-enter">
-      <div
-        className={cn(
-          "inline-flex items-center gap-1.5 px-3 py-1 rounded-full",
-          "bg-leaf-pale border border-leaf-light/50",
-          "text-xs text-leaf-dark italic",
-          pulse && "animate-pulse",
-        )}
-      >
-        {text}
-      </div>
-    </div>
-  ),
-);
diff --git a/raggr-frontend/src/components/artifacts/ArtifactPanel.tsx b/raggr-frontend/src/components/artifacts/ArtifactPanel.tsx
new file mode 100644
index 0000000..fb65e5f
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/ArtifactPanel.tsx
@@ -0,0 +1,384 @@
+import { type ReactNode, useCallback, useEffect, useRef, useState, useSyncExternalStore } from "react";
+import {
+  Library,
+  LoaderCircle,
+  PanelRightClose,
+  PanelRightOpen,
+  RotateCw,
+  TriangleAlert,
+  X,
+} from "lucide-react";
+import { artifactService, type ArtifactListItem } from "../../api/artifactService";
+import type { ArtifactRef } from "../../api/artifactTypes";
+import { cn } from "../../lib/utils";
+import { ArtifactRenderer, kindIcon } from "./renderers";
+import { formatDate } from "./renderers/format";
+import type { ArtifactPanelState } from "./useArtifactPanel";
+
+const DESKTOP_QUERY = "(min-width: 1024px)"; // Tailwind `lg`
+
+function useMediaQuery(query: string): boolean {
+  const subscribe = useCallback(
+    (onChange: () => void) => {
+      const mql = window.matchMedia(query);
+      mql.addEventListener("change", onChange);
+      return () => mql.removeEventListener("change", onChange);
+    },
+    [query],
+  );
+  return useSyncExternalStore(subscribe, () => window.matchMedia(query).matches);
+}
+
+const iconButton =
+  "w-8 h-8 shrink-0 rounded-xl flex items-center justify-center text-warm-gray hover:text-charcoal hover:bg-cream-dark transition-all cursor-pointer";
+
+type ArtifactPanelProps = {
+  panel: ArtifactPanelState;
+  conversationId: string | undefined;
+};
+
+/**
+ * Right-hand artifact pane (lg and up) or bottom sheet (below lg). Renders
+ * nothing until something opens it.
+ */
+export const ArtifactPanel = ({ panel, conversationId }: ArtifactPanelProps) => {
+  const isDesktop = useMediaQuery(DESKTOP_QUERY);
+  const { isOpen, tabs } = panel;
+
+  // Escape closes the mobile sheet.
+  useEffect(() => {
+    if (isDesktop || !isOpen) return;
+    const onKey = (e: KeyboardEvent) => e.key === "Escape" && panel.collapse();
+    window.addEventListener("keydown", onKey);
+    return () => window.removeEventListener("keydown", onKey);
+  }, [isDesktop, isOpen, panel.collapse]);
+
+  if (isDesktop) {
+    if (!isOpen) {
+      if (tabs.length === 0) return null;
+      return <CollapsedRail panel={panel} />;
+    }
+    return (
+      <aside
+        className="w-[440px] shrink-0 flex flex-col h-full border-l border-sand-light/70 bg-warm-white"
+        aria-label="Artifacts"
+      >
+        <PanelHeader panel={panel} closeIcon={<PanelRightClose size={16} />} closeLabel="Collapse panel" />
+        <PanelBody panel={panel} conversationId={conversationId} />
+      </aside>
+    );
+  }
+
+  if (!isOpen) return null;
+  return (
+    <div className="fixed inset-0 z-40 flex flex-col justify-end" role="dialog" aria-label="Artifacts">
+      <div className="absolute inset-0 bg-charcoal/40 backdrop-blur-sm" onClick={panel.collapse} />
+      <div className="relative flex h-[85dvh] flex-col overflow-hidden rounded-t-2xl bg-warm-white shadow-2xl animate-sheet-in">
+        <div className="flex justify-center pt-2">
+          <span className="h-1 w-10 rounded-full bg-sand" />
+        </div>
+        <PanelHeader panel={panel} closeIcon={<X size={16} />} closeLabel="Close artifacts" />
+        <PanelBody panel={panel} conversationId={conversationId} />
+      </div>
+    </div>
+  );
+};
+
+const CollapsedRail = ({ panel }: { panel: ArtifactPanelState }) => (
+  <aside className="w-12 shrink-0 flex flex-col items-center gap-2 py-3 h-full border-l border-sand-light/70 bg-warm-white">
+    <button onClick={panel.expand} className={iconButton} aria-label="Expand artifacts panel">
+      <PanelRightOpen size={16} />
+    </button>
+    <div className="h-px w-6 bg-sand-light" />
+    {panel.tabs.map((tab) => {
+      const Icon = kindIcon(tab.kind);
+      return (
+        <button
+          key={tab.id}
+          onClick={() => panel.open(tab)}
+          title={tab.title}
+          aria-label={`Show ${tab.title}`}
+          className={cn(iconButton, panel.active?.id === tab.id && "text-leaf-dark bg-leaf-pale")}
+        >
+          <Icon size={15} />
+        </button>
+      );
+    })}
+  </aside>
+);
+
+const PanelHeader = ({
+  panel,
+  closeIcon,
+  closeLabel,
+}: {
+  panel: ArtifactPanelState;
+  closeIcon: ReactNode;
+  closeLabel: string;
+}) => {
+  const libraryActive = panel.view === "library" || !panel.active;
+  const stripRef = useRef<HTMLDivElement>(null);
+
+  // Keep the active tab visible when the strip overflows.
+  const activeId = panel.active?.id;
+  useEffect(() => {
+    // The wrapper, so the tab's close button is in view too.
+    stripRef.current
+      ?.querySelector('[aria-selected="true"]')
+      ?.parentElement?.scrollIntoView({ block: "nearest", inline: "nearest" });
+  }, [activeId, libraryActive, panel.tabs.length]);
+
+  return (
+    <div className="flex items-center gap-1 border-b border-sand-light/70 px-2 py-2">
+      <div
+        ref={stripRef}
+        className="flex min-w-0 flex-1 gap-1 overflow-x-auto [scrollbar-width:none]"
+        role="tablist"
+      >
+        {panel.tabs.length === 0 && (
+          <span className="px-2 text-sm font-bold text-charcoal" style={{ fontFamily: "var(--font-display)" }}>
+            Artifacts
+          </span>
+        )}
+        {panel.tabs.map((tab) => (
+          <Tab
+            key={tab.id}
+            tab={tab}
+            selected={!libraryActive && panel.active?.id === tab.id}
+            onSelect={() => panel.open(tab)}
+            onClose={() => panel.close(tab.id)}
+          />
+        ))}
+      </div>
+      <button
+        onClick={() => (libraryActive && panel.active ? panel.setView("tab") : panel.showLibrary())}
+        className={cn(iconButton, libraryActive && "text-leaf-dark bg-leaf-pale")}
+        aria-label="All artifacts in this conversation"
+        aria-pressed={libraryActive}
+        title="All artifacts"
+      >
+        <Library size={16} />
+      </button>
+      <button onClick={panel.collapse} className={iconButton} aria-label={closeLabel} title={closeLabel}>
+        {closeIcon}
+      </button>
+    </div>
+  );
+};
+
+const Tab = ({
+  tab,
+  selected,
+  onSelect,
+  onClose,
+}: {
+  tab: ArtifactRef;
+  selected: boolean;
+  onSelect: () => void;
+  onClose: () => void;
+}) => {
+  const Icon = kindIcon(tab.kind);
+  return (
+    <div
+      className={cn(
+        "group flex min-w-[96px] max-w-[200px] shrink items-center rounded-lg border text-xs transition-colors",
+        selected
+          ? "border-leaf-light bg-leaf-pale text-leaf-dark"
+          : "border-transparent text-warm-gray hover:bg-cream-dark hover:text-charcoal",
+      )}
+    >
+      <button
+        role="tab"
+        aria-selected={selected}
+        onClick={onSelect}
+        title={tab.title}
+        className="flex min-w-0 flex-1 items-center gap-1.5 py-1 pl-2 pr-1 font-semibold cursor-pointer"
+      >
+        <Icon size={13} className="shrink-0" />
+        <span className="truncate">{tab.title}</span>
+      </button>
+      <button
+        onClick={onClose}
+        aria-label={`Close ${tab.title}`}
+        className="mr-1 flex h-5 w-5 shrink-0 items-center justify-center rounded-md opacity-60 hover:bg-sand-light hover:opacity-100 cursor-pointer"
+      >
+        <X size={11} />
+      </button>
+    </div>
+  );
+};
+
+const PanelBody = ({
+  panel,
+  conversationId,
+}: {
+  panel: ArtifactPanelState;
+  conversationId: string | undefined;
+}) => {
+  const { active, activeEntry } = panel;
+  if (panel.view === "library" || !active || !activeEntry) {
+    return (
+      <div className="flex-1 overflow-y-auto px-4 py-4">
+        <ArtifactLibrary conversationId={conversationId} panel={panel} />
+      </div>
+    );
+  }
+
+  return (
+    <div className="flex-1 overflow-y-auto px-4 py-4">
+      {activeEntry.status === "loading" && (
+        <div className="flex flex-col items-center justify-center gap-2 py-16 text-warm-gray">
+          <LoaderCircle size={22} className="animate-spin text-leaf" />
+          <span className="text-sm">Loading {active.title}…</span>
+        </div>
+      )}
+      {activeEntry.status === "error" && (
+        <div className="flex flex-col items-center justify-center gap-3 py-16 text-center">
+          <TriangleAlert size={22} className="text-amber-dark" />
+          <div>
+            <p className="text-sm font-semibold text-charcoal">Couldn&apos;t load this artifact</p>
+            <p className="text-xs text-warm-gray">{activeEntry.error}</p>
+          </div>
+          <button
+            onClick={() => panel.retry(active.id)}
+            className="inline-flex items-center gap-1.5 rounded-xl border border-sand px-3 py-1.5 text-xs font-semibold text-warm-gray hover:bg-cream-dark hover:text-charcoal cursor-pointer"
+          >
+            <RotateCw size={12} /> Retry
+          </button>
+        </div>
+      )}
+      {activeEntry.status === "ready" && (
+        <article key={active.id} className="message-enter">
+          <h2
+            className="mb-3 text-lg font-bold leading-snug text-charcoal"
+            style={{ fontFamily: "var(--font-display)" }}
+          >
+            {activeEntry.artifact.title}
+          </h2>
+          <ArtifactRenderer artifact={activeEntry.artifact} />
+        </article>
+      )}
+    </div>
+  );
+};
+
+type LibraryState =
+  | { status: "loading" }
+  | { status: "error" }
+  | { status: "ready"; items: ArtifactListItem[] };
+
+/** Every artifact in the conversation, newest first, so earlier ones can be reopened. */
+const ArtifactLibrary = ({
+  conversationId,
+  panel,
+}: {
+  conversationId: string | undefined;
+  panel: ArtifactPanelState;
+}) => {
+  const [state, setState] = useState<LibraryState>({ status: "loading" });
+  const [attempt, setAttempt] = useState(0);
+
+  useEffect(() => {
+    if (!conversationId) {
+      setState({ status: "ready", items: [] });
+      return;
+    }
+    let cancelled = false;
+    setState({ status: "loading" });
+    artifactService
+      .listArtifacts(conversationId)
+      .then((items) => {
+        if (cancelled) return;
+        const sorted = [...items].sort((a, b) => b.created_at.localeCompare(a.created_at));
+        setState({ status: "ready", items: sorted });
+      })
+      .catch((err) => {
+        console.error("Failed to list artifacts:", err);
+        if (!cancelled) setState({ status: "error" });
+      });
+    return () => {
+      cancelled = true;
+    };
+  }, [conversationId, attempt]);
+
+  if (state.status === "loading") {
+    return (
+      <ul className="flex flex-col gap-2" aria-busy="true">
+        {[0, 1, 2].map((i) => (
+          <li key={i} className="h-14 rounded-xl bg-sand-light/50 animate-pulse" />
+        ))}
+      </ul>
+    );
+  }
+
+  if (state.status === "error") {
+    return (
+      <div className="flex flex-col items-center gap-3 py-12 text-center">
+        <TriangleAlert size={22} className="text-amber-dark" />
+        <p className="text-sm text-charcoal">Couldn&apos;t load this conversation&apos;s artifacts.</p>
+        <button
+          onClick={() => setAttempt((n) => n + 1)}
+          className="inline-flex items-center gap-1.5 rounded-xl border border-sand px-3 py-1.5 text-xs font-semibold text-warm-gray hover:bg-cream-dark hover:text-charcoal cursor-pointer"
+        >
+          <RotateCw size={12} /> Retry
+        </button>
+      </div>
+    );
+  }
+
+  if (state.items.length === 0) {
+    return (
+      <div className="flex flex-col items-center gap-2 py-12 text-center">
+        <div className="flex h-11 w-11 items-center justify-center rounded-2xl bg-amber-pale text-amber-dark">
+          <Library size={20} />
+        </div>
+        <p className="text-sm font-semibold text-charcoal">No artifacts yet</p>
+        <p className="max-w-[260px] text-xs leading-relaxed text-warm-gray">
+          When Simba pulls up a recipe, a budget, a note or some documents, it shows up here.
+        </p>
+      </div>
+    );
+  }
+
+  const openIds = new Set(panel.tabs.map((t) => t.id));
+  return (
+    <div className="flex flex-col gap-2">
+      <p className="text-[11px] font-bold uppercase tracking-wider text-warm-gray">
+        In this conversation · {state.items.length}
+      </p>
+      <ul className="flex flex-col gap-1.5">
+        {state.items.map((item) => {
+          const Icon = kindIcon(item.kind);
+          return (
+            <li key={item.id}>
+              <button
+                onClick={() => panel.open({ id: item.id, kind: item.kind, title: item.title })}
+                className="flex w-full items-center gap-3 rounded-xl border border-sand-light bg-warm-white px-3 py-2.5 text-left hover:border-leaf-light hover:bg-leaf-pale/50 transition-colors cursor-pointer"
+              >
+                <span className="flex h-8 w-8 shrink-0 items-center justify-center rounded-lg bg-cream-dark text-leaf-dark">
+                  <Icon size={16} />
+                </span>
+                <span className="min-w-0 flex-1">
+                  <span className="block truncate text-sm font-semibold text-charcoal">{item.title}</span>
+                  <span className="block truncate text-[11px] text-warm-gray">
+                    {formatDate(item.created_at, {
+                      month: "short",
+                      day: "numeric",
+                      hour: "numeric",
+                      minute: "2-digit",
+                    })}
+                    {" · "}
+                    {item.tool}
+                  </span>
+                </span>
+                {openIds.has(item.id) && (
+                  <span className="shrink-0 text-[10px] font-bold uppercase tracking-wide text-leaf-dark">Open</span>
+                )}
+              </button>
+            </li>
+          );
+        })}
+      </ul>
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/MealieMealPlan.tsx b/raggr-frontend/src/components/artifacts/renderers/MealieMealPlan.tsx
new file mode 100644
index 0000000..b667545
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/MealieMealPlan.tsx
@@ -0,0 +1,63 @@
+import { formatDate, formatRange } from "./format";
+import { EmptyNote, Subtle } from "./shared";
+import type { MealieMealPlanData, RendererProps } from "./types";
+
+const todayIso = () => {
+  const d = new Date();
+  return `${d.getFullYear()}-${String(d.getMonth() + 1).padStart(2, "0")}-${String(d.getDate()).padStart(2, "0")}`;
+};
+
+export const MealieMealPlan = ({ data }: RendererProps<MealieMealPlanData>) => {
+  const days = [...(data.days ?? [])].sort((a, b) => a.date.localeCompare(b.date));
+  const today = todayIso();
+  return (
+    <div className="flex flex-col gap-3">
+      <Subtle>{formatRange(data.start_date, data.end_date)}</Subtle>
+      {days.length === 0 ? (
+        <EmptyNote>Nothing planned.</EmptyNote>
+      ) : (
+        <ol className="flex flex-col gap-2">
+          {days.map((day) => (
+            <li
+              key={day.date}
+              className={
+                day.date === today
+                  ? "rounded-xl border border-leaf-light bg-leaf-pale/60 px-3 py-2.5"
+                  : "rounded-xl border border-sand-light bg-warm-white px-3 py-2.5"
+              }
+            >
+              <div className="mb-1.5 flex items-baseline gap-2">
+                <span className="text-sm font-bold text-charcoal">
+                  {formatDate(day.date, { weekday: "long" })}
+                </span>
+                <span className="text-xs text-warm-gray">
+                  {formatDate(day.date, { month: "short", day: "numeric" })}
+                </span>
+                {day.date === today && (
+                  <span className="text-[10px] font-bold uppercase tracking-wide text-leaf-dark">Today</span>
+                )}
+              </div>
+              {day.meals.length === 0 ? (
+                <p className="text-xs italic text-warm-gray">Nothing planned</p>
+              ) : (
+                <ul className="flex flex-col gap-1">
+                  {day.meals.map((meal, i) => (
+                    <li key={i} className="flex items-baseline gap-2 text-sm">
+                      <span className="w-[4.5rem] shrink-0 text-[11px] font-semibold uppercase tracking-wide text-amber-dark">
+                        {meal.entry_type}
+                      </span>
+                      <span className="min-w-0">
+                        <span className="text-charcoal">{meal.name}</span>
+                        {meal.note && <span className="block text-xs text-warm-gray">{meal.note}</span>}
+                      </span>
+                    </li>
+                  ))}
+                </ul>
+              )}
+            </li>
+          ))}
+        </ol>
+      )}
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/MealieRecipe.tsx b/raggr-frontend/src/components/artifacts/renderers/MealieRecipe.tsx
new file mode 100644
index 0000000..6ba9a7e
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/MealieRecipe.tsx
@@ -0,0 +1,116 @@
+import { useState } from "react";
+import { Clock, Users } from "lucide-react";
+import { cn } from "../../../lib/utils";
+import { Chip, OpenExternal, SectionTitle } from "./shared";
+import type { MealieRecipeData, RendererProps } from "./types";
+
+export const MealieRecipe = ({ data, sourceRef }: RendererProps<MealieRecipeData>) => {
+  const [ticked, setTicked] = useState<Set<number>>(new Set());
+  const [imageFailed, setImageFailed] = useState(false);
+  const ingredients = data.ingredients ?? [];
+  const instructions = data.instructions ?? [];
+
+  const toggle = (i: number) =>
+    setTicked((prev) => {
+      const next = new Set(prev);
+      if (next.has(i)) next.delete(i);
+      else next.add(i);
+      return next;
+    });
+
+  const times = [
+    ["Prep", data.prep_time],
+    ["Cook", data.cook_time],
+    ["Total", data.total_time],
+  ].filter(([, v]) => v) as [string, string][];
+
+  return (
+    <div className="flex flex-col gap-5">
+      <header className="flex flex-col gap-3">
+        {data.image_url && !imageFailed && (
+          <img
+            src={data.image_url}
+            alt={data.name}
+            onError={() => setImageFailed(true)}
+            className="aspect-[16/9] w-full rounded-xl object-cover border border-sand-light"
+          />
+        )}
+        {/* The panel already titles the artifact with the recipe name. */}
+        {data.description && <p className="text-sm leading-relaxed text-warm-gray">{data.description}</p>}
+        <div className="flex flex-wrap gap-1.5">
+          {times.map(([label, value]) => (
+            <Chip key={label} icon={<Clock size={12} />}>
+              {label} {value}
+            </Chip>
+          ))}
+          {data.servings != null && data.servings !== "" && (
+            <Chip icon={<Users size={12} />}>Serves {data.servings}</Chip>
+          )}
+        </div>
+        {(data.tags?.length ?? 0) > 0 && (
+          <div className="flex flex-wrap gap-1.5">
+            {data.tags.map((t) => (
+              <Chip key={t} tone="leaf">
+                {t}
+              </Chip>
+            ))}
+          </div>
+        )}
+        {sourceRef?.url && (
+          <div>
+            <OpenExternal href={sourceRef.url} label="Open in Mealie" />
+          </div>
+        )}
+      </header>
+
+      {ingredients.length > 0 && (
+        <section>
+          <SectionTitle>
+            Ingredients
+            {ticked.size > 0 && (
+              <span className="ml-1.5 normal-case tracking-normal font-medium">
+                · {ticked.size}/{ingredients.length}
+              </span>
+            )}
+          </SectionTitle>
+          <ul className="flex flex-col gap-0.5">
+            {ingredients.map((ing, i) => (
+              <li key={i}>
+                <label className="flex cursor-pointer items-start gap-2.5 rounded-lg px-2 py-1.5 text-sm hover:bg-cream-dark/60">
+                  <input
+                    type="checkbox"
+                    checked={ticked.has(i)}
+                    onChange={() => toggle(i)}
+                    className="mt-0.5 h-4 w-4 shrink-0 accent-leaf cursor-pointer"
+                  />
+                  <span className={cn(ticked.has(i) ? "text-warm-gray line-through" : "text-charcoal")}>
+                    {ing}
+                  </span>
+                </label>
+              </li>
+            ))}
+          </ul>
+        </section>
+      )}
+
+      {instructions.length > 0 && (
+        <section>
+          <SectionTitle>Steps</SectionTitle>
+          <ol className="flex flex-col gap-3">
+            {instructions.map((step, i) => (
+              <li key={i} className="flex gap-3">
+                <span className="flex h-6 w-6 shrink-0 items-center justify-center rounded-full bg-amber-pale text-xs font-bold text-amber-dark">
+                  {i + 1}
+                </span>
+                <div className="pt-0.5 text-sm leading-relaxed text-charcoal">
+                  {step.title && <div className="font-semibold">{step.title}</div>}
+                  {step.text}
+                </div>
+              </li>
+            ))}
+          </ol>
+        </section>
+      )}
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/MealieShoppingLists.tsx b/raggr-frontend/src/components/artifacts/renderers/MealieShoppingLists.tsx
new file mode 100644
index 0000000..17285dc
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/MealieShoppingLists.tsx
@@ -0,0 +1,51 @@
+import { Check } from "lucide-react";
+import { cn } from "../../../lib/utils";
+import { EmptyNote } from "./shared";
+import type { MealieShoppingListsData, RendererProps } from "./types";
+
+export const MealieShoppingLists = ({ data }: RendererProps<MealieShoppingListsData>) => {
+  const lists = data.lists ?? [];
+  if (lists.length === 0) return <EmptyNote>No shopping lists.</EmptyNote>;
+  return (
+    <div className="flex flex-col gap-4">
+      {lists.map((list) => {
+        const done = list.items.filter((i) => i.checked).length;
+        return (
+          <section key={list.name} className="rounded-xl border border-sand-light bg-warm-white">
+            <header className="flex items-baseline justify-between border-b border-sand-light px-3 py-2">
+              <h3 className="text-sm font-bold text-charcoal">{list.name}</h3>
+              <span className="text-xs text-warm-gray">
+                {done}/{list.items.length} done
+              </span>
+            </header>
+            {list.items.length === 0 ? (
+              <p className="px-3 py-3 text-xs italic text-warm-gray">Empty list</p>
+            ) : (
+              <ul className="divide-y divide-sand-light/60">
+                {list.items.map((item, i) => (
+                  <li key={i} className="flex items-center gap-2.5 px-3 py-1.5 text-sm">
+                    <span
+                      className={cn(
+                        "flex h-4 w-4 shrink-0 items-center justify-center rounded border",
+                        item.checked ? "border-leaf bg-leaf text-white" : "border-sand",
+                      )}
+                    >
+                      {item.checked && <Check size={11} strokeWidth={3} />}
+                    </span>
+                    <span className={cn("flex-1", item.checked ? "text-warm-gray line-through" : "text-charcoal")}>
+                      {item.name}
+                    </span>
+                    {/* Like the tool's text, quantities of 0/1 aren't worth showing. */}
+                    {item.quantity != null && item.quantity !== "" && Number(item.quantity) !== 0 && Number(item.quantity) !== 1 && (
+                      <span className="text-xs tabular-nums text-warm-gray">{item.quantity}</span>
+                    )}
+                  </li>
+                ))}
+              </ul>
+            )}
+          </section>
+        );
+      })}
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/ObsidianNote.tsx b/raggr-frontend/src/components/artifacts/renderers/ObsidianNote.tsx
new file mode 100644
index 0000000..0c413a0
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/ObsidianNote.tsx
@@ -0,0 +1,30 @@
+import ReactMarkdown from "react-markdown";
+import remarkGfm from "remark-gfm";
+import { Chip, OpenExternal, Subtle } from "./shared";
+import type { ObsidianNoteData, RendererProps } from "./types";
+
+export const ObsidianNote = ({ data, sourceRef }: RendererProps<ObsidianNoteData>) => (
+  <div className="flex flex-col gap-4">
+    <header className="flex flex-col gap-2">
+      <Subtle className="font-mono break-all">{data.path}</Subtle>
+      {(data.tags?.length ?? 0) > 0 && (
+        <div className="flex flex-wrap gap-1.5">
+          {data.tags.map((t) => (
+            <Chip key={t} tone="leaf">
+              #{t}
+            </Chip>
+          ))}
+        </div>
+      )}
+      {sourceRef?.url && (
+        <div>
+          <OpenExternal href={sourceRef.url} label="Open in Obsidian" />
+        </div>
+      )}
+    </header>
+    {/* Tailwind's preflight strips list markers; notes need them back. */}
+    <div className="markdown-content text-[15px] leading-relaxed text-charcoal [&_ul]:list-disc [&_ol]:list-decimal [&_ul.contains-task-list]:list-none [&_ul.contains-task-list]:pl-1">
+      <ReactMarkdown remarkPlugins={[remarkGfm]}>{data.markdown ?? ""}</ReactMarkdown>
+    </div>
+  </div>
+);
diff --git a/raggr-frontend/src/components/artifacts/renderers/SearchDocuments.tsx b/raggr-frontend/src/components/artifacts/renderers/SearchDocuments.tsx
new file mode 100644
index 0000000..730cf62
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/SearchDocuments.tsx
@@ -0,0 +1,48 @@
+import { FileText } from "lucide-react";
+import { formatDate } from "./format";
+import { EmptyNote, Subtle } from "./shared";
+import type { RendererProps, SearchDocumentsData } from "./types";
+
+export const SearchDocuments = ({ data }: RendererProps<SearchDocumentsData>) => {
+  const results = data.results ?? [];
+  return (
+    <div className="flex flex-col gap-3">
+      <Subtle>
+        “{data.query}” in {data.source} · {results.length} result{results.length === 1 ? "" : "s"}
+      </Subtle>
+      {results.length === 0 ? (
+        <EmptyNote>No matching documents.</EmptyNote>
+      ) : (
+        <ul className="flex flex-col gap-2">
+          {results.map((r, i) => {
+            const location = r.filename ?? r.path;
+            return (
+              <li key={i} className="rounded-xl border border-sand-light bg-warm-white px-3 py-2.5">
+                <div className="flex items-start justify-between gap-2">
+                  <h4 className="text-sm font-bold leading-snug text-charcoal">{r.title}</h4>
+                  {r.document_type && (
+                    <span className="shrink-0 rounded-full bg-amber-pale px-2 py-0.5 text-[10px] font-semibold text-amber-dark">
+                      {r.document_type}
+                    </span>
+                  )}
+                </div>
+                <p className="mt-1 text-[13px] leading-relaxed text-charcoal/80 line-clamp-4">{r.snippet}</p>
+                {(location || r.date) && (
+                  <div className="mt-1.5 flex items-center gap-2 text-[11px] text-warm-gray">
+                    {location && (
+                      <span className="flex min-w-0 items-center gap-1">
+                        <FileText size={11} className="shrink-0" />
+                        <span className="truncate font-mono">{location}</span>
+                      </span>
+                    )}
+                    {r.date && <span className="ml-auto shrink-0">{formatDate(r.date)}</span>}
+                  </div>
+                )}
+              </li>
+            );
+          })}
+        </ul>
+      )}
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/UnknownArtifact.tsx b/raggr-frontend/src/components/artifacts/renderers/UnknownArtifact.tsx
new file mode 100644
index 0000000..5800298
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/UnknownArtifact.tsx
@@ -0,0 +1,12 @@
+import { Subtle } from "./shared";
+
+export const UnknownArtifact = ({ kind, data }: { kind: string; data: unknown }) => (
+  <div className="flex flex-col gap-2">
+    <Subtle>
+      No viewer for <code className="font-mono">{kind}</code> yet; showing the raw data.
+    </Subtle>
+    <pre className="overflow-x-auto rounded-xl bg-charcoal p-3 text-xs leading-relaxed text-cream-dark">
+      {JSON.stringify(data, null, 2)}
+    </pre>
+  </div>
+);
diff --git a/raggr-frontend/src/components/artifacts/renderers/YnabCategoryBudget.tsx b/raggr-frontend/src/components/artifacts/renderers/YnabCategoryBudget.tsx
new file mode 100644
index 0000000..c27b73c
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/YnabCategoryBudget.tsx
@@ -0,0 +1,83 @@
+import { cn } from "../../../lib/utils";
+import { formatMoney, formatMonth, moneyTone } from "./format";
+import { EmptyNote } from "./shared";
+import type { RendererProps, YnabCategoryBudgetData } from "./types";
+
+type Category = YnabCategoryBudgetData["groups"][number]["categories"][number];
+
+/** Available as a share of assigned; full when nothing was assigned but money is available. */
+function availableShare(c: Category): number {
+  if (c.available <= 0) return 0;
+  if (c.assigned <= 0) return 1;
+  return Math.min(1, c.available / c.assigned);
+}
+
+const sum = (cats: Category[], key: "assigned" | "activity" | "available") =>
+  cats.reduce((acc, c) => acc + (c[key] ?? 0), 0);
+
+export const YnabCategoryBudget = ({ data }: RendererProps<YnabCategoryBudgetData>) => {
+  const groups = (data.groups ?? []).filter((g) => g.categories?.length);
+  if (groups.length === 0) return <EmptyNote>No categories for this month.</EmptyNote>;
+
+  return (
+    <div className="flex flex-col gap-3">
+      <p className="text-sm text-warm-gray">{formatMonth(data.month)}</p>
+      <div className="overflow-x-auto rounded-xl border border-sand-light bg-warm-white">
+        <table className="w-full text-xs tabular-nums">
+          <thead>
+            <tr className="border-b border-sand-light text-[11px] uppercase tracking-wide text-warm-gray">
+              <th className="px-3 py-2 text-left font-semibold">Category</th>
+              <th className="px-2 py-2 text-right font-semibold">Assigned</th>
+              <th className="px-2 py-2 text-right font-semibold">Activity</th>
+              <th className="px-3 py-2 text-right font-semibold">Available</th>
+            </tr>
+          </thead>
+          {groups.map((group) => (
+            <tbody key={group.name}>
+              <tr className="bg-sand-light/50 font-bold text-charcoal">
+                <td className="px-3 py-1.5">{group.name}</td>
+                <td className="px-2 py-1.5 text-right">{formatMoney(sum(group.categories, "assigned"))}</td>
+                <td className="px-2 py-1.5 text-right">{formatMoney(sum(group.categories, "activity"), { signed: true })}</td>
+                <td className={cn("px-3 py-1.5 text-right", moneyTone(sum(group.categories, "available")))}>
+                  {formatMoney(sum(group.categories, "available"))}
+                </td>
+              </tr>
+              {group.categories.map((c) => {
+                const overspent = c.available < 0;
+                return (
+                  <tr
+                    key={c.name}
+                    className={cn("border-t border-sand-light/60", overspent && "bg-red-50")}
+                  >
+                    <td className="px-3 py-1.5 align-top">
+                      <div className={cn("truncate max-w-[150px]", overspent ? "text-red-700 font-semibold" : "text-charcoal")}>
+                        {c.name}
+                      </div>
+                      <div className="mt-1 h-1.5 w-full max-w-[150px] rounded-full bg-sand-light overflow-hidden">
+                        <div
+                          className={cn(
+                            "h-full rounded-full",
+                            overspent ? "bg-red-400 w-full" : "bg-leaf",
+                          )}
+                          style={overspent ? undefined : { width: `${availableShare(c) * 100}%` }}
+                        />
+                      </div>
+                    </td>
+                    <td className="px-2 py-1.5 text-right align-top text-charcoal">{formatMoney(c.assigned)}</td>
+                    <td className={cn("px-2 py-1.5 text-right align-top", c.activity < 0 ? "text-warm-gray" : "text-leaf-dark")}>
+                      {formatMoney(c.activity, { signed: true })}
+                    </td>
+                    <td className={cn("px-3 py-1.5 text-right align-top font-semibold", overspent ? "text-red-600" : "text-leaf-dark")}>
+                      {formatMoney(c.available)}
+                    </td>
+                  </tr>
+                );
+              })}
+            </tbody>
+          ))}
+        </table>
+      </div>
+      <p className="text-[11px] text-warm-gray">Bar: available as a share of assigned. Red rows are overspent.</p>
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/YnabSpendingReport.tsx b/raggr-frontend/src/components/artifacts/renderers/YnabSpendingReport.tsx
new file mode 100644
index 0000000..39db77c
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/YnabSpendingReport.tsx
@@ -0,0 +1,104 @@
+import { formatDate, formatMoney, formatRange } from "./format";
+import { EmptyNote, Subtle } from "./shared";
+import type { RendererProps, YnabSpendingReportData } from "./types";
+
+type Row = YnabSpendingReportData["rows"][number];
+
+/** "2026-08" → "Aug" (or "Aug 26" when the rows span years); anything else as-is. */
+const monthLabel = (key: string, withYear: boolean) =>
+  /^\d{4}-\d{2}/.test(key)
+    ? formatDate(key, withYear ? { month: "short", year: "2-digit" } : { month: "short" })
+    : key;
+
+const MonthBars = ({ rows }: { rows: Row[] }) => {
+  const ordered = [...rows].sort((a, b) => a.key.localeCompare(b.key));
+  const withYear = new Set(ordered.map((r) => r.key.slice(0, 4))).size > 1;
+  const label = (key: string) => monthLabel(key, withYear);
+  const max = Math.max(...ordered.map((r) => r.amount), 1);
+  return (
+    <div className="rounded-xl border border-sand-light bg-warm-white px-3 pt-4 pb-2">
+      <div className="flex h-44 items-end gap-1.5">
+        {ordered.map((r) => (
+          <div
+            key={r.key}
+            className="group flex h-full min-w-0 flex-1 flex-col items-center justify-end gap-1"
+            title={`${monthLabel(r.key, true)}: ${formatMoney(r.amount)}`}
+          >
+            <span className="text-[10px] font-semibold tabular-nums text-warm-gray opacity-0 group-hover:opacity-100 transition-opacity whitespace-nowrap">
+              {formatMoney(r.amount).replace(/\.\d\d$/, "")}
+            </span>
+            <div
+              className="w-full max-w-10 rounded-t-md bg-amber-glow/80 group-hover:bg-amber-dark transition-colors"
+              style={{ height: `${Math.max(2, (Math.max(0, r.amount) / max) * 100)}%` }}
+            />
+          </div>
+        ))}
+      </div>
+      <div className="mt-1.5 flex gap-1.5 border-t border-sand-light pt-1.5">
+        {ordered.map((r) => (
+          <span key={r.key} className="min-w-0 flex-1 truncate text-center text-[10px] text-warm-gray">
+            {label(r.key)}
+          </span>
+        ))}
+      </div>
+    </div>
+  );
+};
+
+const HorizontalBars = ({ rows }: { rows: Row[] }) => {
+  // Amounts are positive spending; a net refund (negative) sorts last with no bar.
+  const ordered = [...rows].sort((a, b) => b.amount - a.amount);
+  const max = Math.max(...ordered.map((r) => r.amount), 1);
+  return (
+    <ul className="flex flex-col gap-2.5">
+      {ordered.map((r) => (
+        <li key={r.key}>
+          <div className="flex items-baseline justify-between gap-3 text-sm">
+            <span className="truncate text-charcoal">{r.key}</span>
+            <span className={`shrink-0 font-semibold tabular-nums ${r.amount < 0 ? "text-leaf-dark" : "text-charcoal"}`}>
+              {formatMoney(r.amount)}
+            </span>
+          </div>
+          <div className="mt-1 flex items-center gap-2">
+            <div className="h-2 flex-1 rounded-full bg-sand-light/70 overflow-hidden">
+              <div
+                className="h-full rounded-full bg-leaf"
+                style={{ width: `${(Math.max(0, r.amount) / max) * 100}%` }}
+              />
+            </div>
+            {r.count != null && (
+              <span className="w-12 shrink-0 text-right text-[11px] text-warm-gray">
+                {r.count} txn{r.count === 1 ? "" : "s"}
+              </span>
+            )}
+          </div>
+        </li>
+      ))}
+    </ul>
+  );
+};
+
+export const YnabSpendingReport = ({ data }: RendererProps<YnabSpendingReportData>) => {
+  const rows = data.rows ?? [];
+  return (
+    <div className="flex flex-col gap-4">
+      <div className="flex items-end justify-between gap-3">
+        <div>
+          <Subtle>{formatRange(data.start_date, data.end_date)}</Subtle>
+          <Subtle>Grouped by {data.group_by?.replace(/_/g, " ")}</Subtle>
+        </div>
+        <div className="text-right">
+          <div className="text-[11px] font-semibold uppercase tracking-wide text-warm-gray">Total</div>
+          <div className="text-xl font-bold tabular-nums text-charcoal">{formatMoney(data.total)}</div>
+        </div>
+      </div>
+      {rows.length === 0 ? (
+        <EmptyNote>No spending in this period.</EmptyNote>
+      ) : data.group_by === "month" ? (
+        <MonthBars rows={rows} />
+      ) : (
+        <HorizontalBars rows={rows} />
+      )}
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/YnabSummary.tsx b/raggr-frontend/src/components/artifacts/renderers/YnabSummary.tsx
new file mode 100644
index 0000000..07bce9a
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/YnabSummary.tsx
@@ -0,0 +1,48 @@
+import { formatMoney, formatMonth } from "./format";
+import { EmptyNote, SectionTitle, StatTile } from "./shared";
+import type { RendererProps, YnabSummaryData } from "./types";
+
+export const YnabSummary = ({ data }: RendererProps<YnabSummaryData>) => {
+  const overspent = data.overspent ?? [];
+  return (
+    <div className="flex flex-col gap-5">
+      <p className="text-sm text-warm-gray">{formatMonth(data.month)}</p>
+      <div className="grid grid-cols-2 gap-2">
+        <StatTile
+          label="Ready to assign"
+          value={formatMoney(data.ready_to_assign)}
+          tone={data.ready_to_assign < 0 ? "bad" : "good"}
+        />
+        <StatTile label="Income" value={formatMoney(data.income)} />
+        <StatTile label="Assigned" value={formatMoney(data.assigned)} />
+        {/* Positive for spending, like the spending report. */}
+        <StatTile label="Spent" value={formatMoney(data.spent)} />
+        <StatTile
+          label="Net worth"
+          value={formatMoney(data.net_worth)}
+          tone={data.net_worth < 0 ? "bad" : "default"}
+        />
+        {data.age_of_money != null && (
+          <StatTile label="Age of money" value={`${data.age_of_money} days`} />
+        )}
+      </div>
+      <section>
+        <SectionTitle>Overspent ({overspent.length})</SectionTitle>
+        {overspent.length === 0 ? (
+          <EmptyNote>Nothing overspent this month.</EmptyNote>
+        ) : (
+          <ul className="divide-y divide-red-100 rounded-xl border border-red-200 bg-red-50/60">
+            {overspent.map((c) => (
+              <li key={c.name} className="flex items-center justify-between px-3 py-2 text-sm">
+                <span className="text-charcoal">{c.name}</span>
+                <span className="font-semibold tabular-nums text-red-600">
+                  {formatMoney(c.available)}
+                </span>
+              </li>
+            ))}
+          </ul>
+        )}
+      </section>
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/YnabTransactions.tsx b/raggr-frontend/src/components/artifacts/renderers/YnabTransactions.tsx
new file mode 100644
index 0000000..1c418c4
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/YnabTransactions.tsx
@@ -0,0 +1,118 @@
+import { useMemo, useState } from "react";
+import { ArrowDown, ArrowUp, ArrowUpDown } from "lucide-react";
+import { cn } from "../../../lib/utils";
+import { formatDate, formatMoney, formatRange } from "./format";
+import { EmptyNote, Subtle } from "./shared";
+import type { RendererProps, YnabTransactionsData } from "./types";
+
+type SortKey = "date" | "payee" | "category" | "amount";
+type Sort = { key: SortKey; dir: "asc" | "desc" };
+
+const COLUMNS: { key: SortKey; label: string; align: "left" | "right" }[] = [
+  { key: "date", label: "Date", align: "left" },
+  { key: "payee", label: "Payee", align: "left" },
+  { key: "category", label: "Category", align: "left" },
+  { key: "amount", label: "Amount", align: "right" },
+];
+
+export const YnabTransactions = ({ data }: RendererProps<YnabTransactionsData>) => {
+  const [sort, setSort] = useState<Sort>({ key: "date", dir: "desc" });
+  const transactions = data.transactions ?? [];
+
+  const sorted = useMemo(() => {
+    const factor = sort.dir === "asc" ? 1 : -1;
+    return [...transactions].sort((a, b) => {
+      const cmp =
+        sort.key === "amount"
+          ? a.amount - b.amount
+          : String(a[sort.key] ?? "").localeCompare(String(b[sort.key] ?? ""));
+      return cmp * factor;
+    });
+  }, [transactions, sort]);
+
+  const toggle = (key: SortKey) =>
+    setSort((s) =>
+      s.key === key
+        ? { key, dir: s.dir === "asc" ? "desc" : "asc" }
+        : { key, dir: key === "date" || key === "amount" ? "desc" : "asc" },
+    );
+
+  if (transactions.length === 0) return <EmptyNote>No matching transactions.</EmptyNote>;
+
+  return (
+    <div className="flex flex-col gap-3">
+      <Subtle>
+        {formatRange(data.start_date, data.end_date)} · {data.count} transaction
+        {data.count === 1 ? "" : "s"}
+        {data.count > transactions.length && ` (showing ${transactions.length})`}
+      </Subtle>
+      <div className="overflow-x-auto rounded-xl border border-sand-light bg-warm-white">
+        <table className="w-full text-xs">
+          <thead>
+            <tr className="border-b border-sand-light">
+              {COLUMNS.map((col) => {
+                const activeCol = sort.key === col.key;
+                const Icon = !activeCol ? ArrowUpDown : sort.dir === "asc" ? ArrowUp : ArrowDown;
+                return (
+                  <th
+                    key={col.key}
+                    className={cn("px-2 py-2 first:pl-3 last:pr-3", col.align === "right" ? "text-right" : "text-left")}
+                    aria-sort={activeCol ? (sort.dir === "asc" ? "ascending" : "descending") : "none"}
+                  >
+                    <button
+                      onClick={() => toggle(col.key)}
+                      className={cn(
+                        "inline-flex items-center gap-1 text-[11px] font-semibold uppercase tracking-wide cursor-pointer hover:text-charcoal",
+                        activeCol ? "text-charcoal" : "text-warm-gray",
+                      )}
+                    >
+                      {col.label}
+                      <Icon size={11} className={activeCol ? "" : "opacity-40"} />
+                    </button>
+                  </th>
+                );
+              })}
+            </tr>
+          </thead>
+          <tbody>
+            {sorted.map((t, i) => (
+              <tr key={i} className="border-t border-sand-light/60 align-top">
+                <td className="whitespace-nowrap py-1.5 pl-3 pr-2 text-warm-gray">
+                  {formatDate(t.date, { month: "short", day: "numeric" })}
+                </td>
+                <td className="px-2 py-1.5">
+                  <div className="text-charcoal">{t.payee}</div>
+                  {t.memo && <div className="text-[11px] text-warm-gray">{t.memo}</div>}
+                </td>
+                <td className="px-2 py-1.5 text-warm-gray">{t.category}</td>
+                <td
+                  className={cn(
+                    "whitespace-nowrap py-1.5 pl-2 pr-3 text-right font-semibold tabular-nums",
+                    t.amount < 0 ? "text-charcoal" : "text-leaf-dark",
+                  )}
+                >
+                  {formatMoney(t.amount, { signed: true })}
+                </td>
+              </tr>
+            ))}
+          </tbody>
+          <tfoot>
+            <tr className="border-t-2 border-sand bg-sand-light/40 font-bold">
+              <td className="py-2 pl-3 pr-2 text-charcoal" colSpan={3}>
+                Total
+              </td>
+              <td
+                className={cn(
+                  "whitespace-nowrap py-2 pl-2 pr-3 text-right tabular-nums",
+                  data.total < 0 ? "text-charcoal" : "text-leaf-dark",
+                )}
+              >
+                {formatMoney(data.total, { signed: true })}
+              </td>
+            </tr>
+          </tfoot>
+        </table>
+      </div>
+    </div>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/format.ts b/raggr-frontend/src/components/artifacts/renderers/format.ts
new file mode 100644
index 0000000..d276391
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/format.ts
@@ -0,0 +1,51 @@
+const usd = new Intl.NumberFormat("en-US", {
+  style: "currency",
+  currency: "USD",
+  minimumFractionDigits: 2,
+  maximumFractionDigits: 2,
+});
+
+/**
+ * USD with an explicit sign: "−$12.50" for negatives and, when `signed`,
+ * "+$12.50" for positives. Amounts are dollars, not YNAB milliunits.
+ */
+export function formatMoney(amount: number, { signed = false } = {}): string {
+  const value = Number.isFinite(amount) ? amount : 0;
+  const abs = usd.format(Math.abs(value));
+  if (value < 0) return `−${abs}`;
+  if (signed && value > 0) return `+${abs}`;
+  return abs;
+}
+
+/** Tailwind text colour for a money value: red when negative. */
+export function moneyTone(amount: number): string {
+  return amount < 0 ? "text-red-600" : "text-charcoal";
+}
+
+/** Parse a bare "YYYY-MM[-DD]" as a local date (avoids the UTC off-by-one). */
+function parseDate(value: string): Date | null {
+  const m = /^(\d{4})-(\d{2})(?:-(\d{2}))?$/.exec(value);
+  if (m) return new Date(Number(m[1]), Number(m[2]) - 1, Number(m[3] ?? 1));
+  const d = new Date(value);
+  return Number.isNaN(d.getTime()) ? null : d;
+}
+
+export function formatDate(
+  value: string | null | undefined,
+  options: Intl.DateTimeFormatOptions = { month: "short", day: "numeric", year: "numeric" },
+): string {
+  if (!value) return "";
+  const d = parseDate(value);
+  return d ? d.toLocaleDateString("en-US", options) : value;
+}
+
+/** "2026-10" or "2026-10-01" → "October 2026". */
+export function formatMonth(value: string | null | undefined): string {
+  return formatDate(value, { month: "long", year: "numeric" });
+}
+
+export function formatRange(start?: string | null, end?: string | null): string {
+  if (start && end) return `${formatDate(start)} – ${formatDate(end)}`;
+  if (end) return `Through ${formatDate(end)}`;
+  return start ? `From ${formatDate(start)}` : "";
+}
diff --git a/raggr-frontend/src/components/artifacts/renderers/index.tsx b/raggr-frontend/src/components/artifacts/renderers/index.tsx
new file mode 100644
index 0000000..eab1d51
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/index.tsx
@@ -0,0 +1,84 @@
+import React from "react";
+import {
+  CalendarDays,
+  ChartColumn,
+  ChefHat,
+  NotebookText,
+  PiggyBank,
+  Receipt,
+  Search,
+  Shapes,
+  ShoppingCart,
+  Wallet,
+  type LucideIcon,
+} from "lucide-react";
+import type { Artifact } from "../../../api/artifactTypes";
+import { MealieMealPlan } from "./MealieMealPlan";
+import { MealieRecipe } from "./MealieRecipe";
+import { MealieShoppingLists } from "./MealieShoppingLists";
+import { ObsidianNote } from "./ObsidianNote";
+import { SearchDocuments } from "./SearchDocuments";
+import { UnknownArtifact } from "./UnknownArtifact";
+import { YnabCategoryBudget } from "./YnabCategoryBudget";
+import { YnabSpendingReport } from "./YnabSpendingReport";
+import { YnabSummary } from "./YnabSummary";
+import { YnabTransactions } from "./YnabTransactions";
+import type { RendererProps } from "./types";
+
+// biome-ignore lint/suspicious/noExplicitAny: each renderer narrows its own data shape
+const RENDERERS: Record<string, React.ComponentType<RendererProps<any>>> = {
+  "ynab.summary": YnabSummary,
+  "ynab.category_budget": YnabCategoryBudget,
+  "ynab.spending_report": YnabSpendingReport,
+  "ynab.transactions": YnabTransactions,
+  "mealie.recipe": MealieRecipe,
+  "mealie.meal_plan": MealieMealPlan,
+  "mealie.shopping_lists": MealieShoppingLists,
+  "obsidian.note": ObsidianNote,
+  "search.documents": SearchDocuments,
+};
+
+const KIND_ICONS: Record<string, LucideIcon> = {
+  "ynab.summary": PiggyBank,
+  "ynab.category_budget": Wallet,
+  "ynab.spending_report": ChartColumn,
+  "ynab.transactions": Receipt,
+  "mealie.recipe": ChefHat,
+  "mealie.meal_plan": CalendarDays,
+  "mealie.shopping_lists": ShoppingCart,
+  "obsidian.note": NotebookText,
+  "search.documents": Search,
+};
+
+export const kindIcon = (kind: string): LucideIcon => KIND_ICONS[kind] ?? Shapes;
+
+/** Falls back to the raw JSON if a renderer throws on an unexpected payload. */
+class RenderBoundary extends React.Component<
+  { kind: string; data: unknown; children: React.ReactNode },
+  { failed: boolean }
+> {
+  state = { failed: false };
+
+  static getDerivedStateFromError() {
+    return { failed: true };
+  }
+
+  componentDidCatch(error: unknown) {
+    console.error(`Artifact renderer for ${this.props.kind} failed:`, error);
+  }
+
+  render() {
+    if (this.state.failed) return <UnknownArtifact kind={this.props.kind} data={this.props.data} />;
+    return this.props.children;
+  }
+}
+
+export const ArtifactRenderer = ({ artifact }: { artifact: Artifact }) => {
+  const Renderer = RENDERERS[artifact.kind];
+  if (!Renderer) return <UnknownArtifact kind={artifact.kind} data={artifact.data} />;
+  return (
+    <RenderBoundary key={artifact.id} kind={artifact.kind} data={artifact.data}>
+      <Renderer data={artifact.data} sourceRef={artifact.source_ref} />
+    </RenderBoundary>
+  );
+};
diff --git a/raggr-frontend/src/components/artifacts/renderers/shared.tsx b/raggr-frontend/src/components/artifacts/renderers/shared.tsx
new file mode 100644
index 0000000..09c8364
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/shared.tsx
@@ -0,0 +1,77 @@
+import type React from "react";
+import { ExternalLink } from "lucide-react";
+import { cn } from "../../../lib/utils";
+
+export const SectionTitle = ({ children }: { children: React.ReactNode }) => (
+  <h3 className="text-[11px] font-bold uppercase tracking-wider text-warm-gray mb-2">
+    {children}
+  </h3>
+);
+
+export const Subtle = ({ children, className }: { children: React.ReactNode; className?: string }) => (
+  <p className={cn("text-xs text-warm-gray", className)}>{children}</p>
+);
+
+export const Chip = ({
+  icon,
+  children,
+  tone = "sand",
+}: {
+  icon?: React.ReactNode;
+  children: React.ReactNode;
+  tone?: "sand" | "leaf" | "amber";
+}) => (
+  <span
+    className={cn(
+      "inline-flex items-center gap-1 rounded-full px-2.5 py-0.5 text-xs font-medium",
+      tone === "sand" && "bg-sand-light/70 text-charcoal",
+      tone === "leaf" && "bg-leaf-pale text-leaf-dark border border-leaf-light/50",
+      tone === "amber" && "bg-amber-pale text-amber-dark",
+    )}
+  >
+    {icon}
+    {children}
+  </span>
+);
+
+export const StatTile = ({
+  label,
+  value,
+  tone = "default",
+}: {
+  label: string;
+  value: React.ReactNode;
+  tone?: "default" | "good" | "bad";
+}) => (
+  <div className="rounded-xl border border-sand-light bg-warm-white px-3 py-2.5">
+    <div className="text-[11px] font-semibold uppercase tracking-wide text-warm-gray">{label}</div>
+    <div
+      className={cn(
+        "mt-0.5 text-lg font-bold tabular-nums",
+        tone === "default" && "text-charcoal",
+        tone === "good" && "text-leaf-dark",
+        tone === "bad" && "text-red-600",
+      )}
+    >
+      {value}
+    </div>
+  </div>
+);
+
+export const OpenExternal = ({ href, label }: { href: string; label: string }) => (
+  <a
+    href={href}
+    target="_blank"
+    rel="noreferrer"
+    className="inline-flex items-center gap-1.5 rounded-xl border border-sand bg-warm-white px-3 py-1.5 text-xs font-semibold text-leaf-dark hover:bg-leaf-pale hover:border-leaf-light transition-colors"
+  >
+    <ExternalLink size={13} />
+    {label}
+  </a>
+);
+
+export const EmptyNote = ({ children }: { children: React.ReactNode }) => (
+  <p className="rounded-xl border border-dashed border-sand px-3 py-4 text-center text-sm text-warm-gray">
+    {children}
+  </p>
+);
diff --git a/raggr-frontend/src/components/artifacts/renderers/types.ts b/raggr-frontend/src/components/artifacts/renderers/types.ts
new file mode 100644
index 0000000..fd7413e
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/renderers/types.ts
@@ -0,0 +1,110 @@
+// Per-kind `data` shapes (docs/cowork-ui-plan.md § V1 kinds). Renderers treat
+// them as best-effort: optional chaining guards against partial payloads.
+
+import type { ArtifactSourceRef } from "../../../api/artifactTypes";
+
+export type SourceRef = ArtifactSourceRef;
+
+export type MealieRecipeData = {
+  slug: string;
+  name: string;
+  description: string | null;
+  servings: string | number | null;
+  prep_time: string | null;
+  cook_time: string | null;
+  total_time: string | null;
+  ingredients: string[];
+  instructions: { title?: string; text: string }[];
+  tags: string[];
+  image_url?: string; // in the contract, not sent by the backend today
+};
+
+export type MealieMealPlanData = {
+  start_date: string;
+  end_date: string;
+  days: {
+    date: string;
+    meals: { entry_type: string; name: string; recipe_slug?: string; note?: string }[];
+  }[];
+};
+
+export type MealieShoppingListsData = {
+  lists: { name: string; items: { name: string; quantity: number | string | null; checked: boolean }[] }[];
+};
+
+export type ObsidianNoteData = {
+  path: string;
+  title: string;
+  markdown: string;
+  tags: string[];
+  frontmatter: Record<string, unknown>;
+};
+
+export type SearchDocumentsData = {
+  query: string;
+  source: string;
+  results: {
+    title: string;
+    snippet: string;
+    filename?: string;
+    path?: string;
+    document_type?: string;
+    date?: string;
+  }[];
+};
+
+export type YnabSummaryData = {
+  month: string;
+  ready_to_assign: number;
+  income: number;
+  assigned: number;
+  /** Positive for spending (-SUM of outflows). */
+  spent: number;
+  age_of_money?: number | null;
+  net_worth: number;
+  overspent: { name: string; available: number }[];
+};
+
+export type YnabTransactionsData = {
+  /** Null for open-ended searches ("all time through end_date"). */
+  start_date: string | null;
+  end_date: string;
+  count: number;
+  /** Net of outflows and inflows. */
+  total: number;
+  transactions: {
+    date: string;
+    payee: string;
+    category: string;
+    account: string;
+    memo?: string | null;
+    /** Signed: negative = outflow. */
+    amount: number;
+  }[];
+};
+
+export type YnabSpendingReportData = {
+  start_date: string;
+  end_date: string;
+  group_by: "category" | "category_group" | "payee" | "account" | "month" | string;
+  /** amount is positive for spending (-SUM); a net refund comes out negative. */
+  rows: { key: string; amount: number; count?: number }[];
+  total: number;
+};
+
+export type YnabCategoryBudgetData = {
+  month: string;
+  groups: {
+    name: string;
+    categories: {
+      name: string;
+      assigned: number;
+      /** Negative for spending. */
+      activity: number;
+      available: number;
+      goal_target?: number | null;
+    }[];
+  }[];
+};
+
+export type RendererProps<T> = { data: T; sourceRef: SourceRef | null };
diff --git a/raggr-frontend/src/components/artifacts/useArtifactPanel.ts b/raggr-frontend/src/components/artifacts/useArtifactPanel.ts
new file mode 100644
index 0000000..1c43561
--- /dev/null
+++ b/raggr-frontend/src/components/artifacts/useArtifactPanel.ts
@@ -0,0 +1,118 @@
+import { useCallback, useEffect, useRef, useState } from "react";
+import { artifactService } from "../../api/artifactService";
+import type { Artifact, ArtifactRef } from "../../api/artifactTypes";
+
+/** Windows at least this wide auto-open artifacts as tools produce them. */
+export const AUTO_OPEN_MIN_WIDTH = 1280;
+
+export type ArtifactEntry =
+  | { status: "loading" }
+  | { status: "error"; error: string }
+  | { status: "ready"; artifact: Artifact };
+
+export type ArtifactPanelView = "tab" | "library";
+
+type OpenOptions = {
+  /** Set for automatic opens; they don't re-expand a panel the user collapsed. */
+  auto?: boolean;
+};
+
+/**
+ * State for the right-hand artifact panel: the open tabs, which one is
+ * active, and a per-id cache of fetched artifacts. Tabs reset whenever the
+ * conversation changes; the cache survives (artifact ids are unique).
+ */
+export function useArtifactPanel(conversationId: string | undefined) {
+  const [tabs, setTabs] = useState<ArtifactRef[]>([]);
+  const [activeId, setActiveId] = useState<string | null>(null);
+  const [isOpen, setIsOpen] = useState(false);
+  const [view, setView] = useState<ArtifactPanelView>("tab");
+  const [cache, setCache] = useState<Record<string, ArtifactEntry>>({});
+
+  const cacheRef = useRef(cache);
+  cacheRef.current = cache;
+  // Set when the user collapses the panel, so auto-opens stop forcing it open.
+  const userCollapsedRef = useRef(false);
+
+  useEffect(() => {
+    setTabs([]);
+    setActiveId(null);
+    setIsOpen(false);
+    setView("tab");
+    userCollapsedRef.current = false;
+  }, [conversationId]);
+
+  const load = useCallback(async (id: string) => {
+    setCache((prev) => ({ ...prev, [id]: { status: "loading" } }));
+    try {
+      const artifact = await artifactService.getArtifact(id);
+      setCache((prev) => ({ ...prev, [id]: { status: "ready", artifact } }));
+    } catch (err) {
+      const error = err instanceof Error ? err.message : "Failed to load artifact";
+      setCache((prev) => ({ ...prev, [id]: { status: "error", error } }));
+    }
+  }, []);
+
+  const open = useCallback(
+    (ref: ArtifactRef, { auto = false }: OpenOptions = {}) => {
+      setTabs((prev) => (prev.some((t) => t.id === ref.id) ? prev : [...prev, ref]));
+      setActiveId(ref.id);
+      setView("tab");
+      if (!auto || !userCollapsedRef.current) setIsOpen(true);
+      const cached = cacheRef.current[ref.id];
+      if (!cached || cached.status === "error") load(ref.id);
+    },
+    [load],
+  );
+
+  const close = useCallback(
+    (id: string) => {
+      const index = tabs.findIndex((t) => t.id === id);
+      if (index === -1) return;
+      const next = tabs.filter((t) => t.id !== id);
+      setTabs(next);
+      // Activate the neighbour (right, else left) when the active tab closes.
+      if (activeId === id) setActiveId((next[index] ?? next[index - 1])?.id ?? null);
+      if (next.length === 0) setView("library");
+    },
+    [tabs, activeId],
+  );
+
+  const retry = useCallback((id: string) => load(id), [load]);
+
+  const expand = useCallback(() => {
+    userCollapsedRef.current = false;
+    setIsOpen(true);
+  }, []);
+
+  const collapse = useCallback(() => {
+    userCollapsedRef.current = true;
+    setIsOpen(false);
+  }, []);
+
+  /** Open the panel on the list of this conversation's artifacts. */
+  const showLibrary = useCallback(() => {
+    userCollapsedRef.current = false;
+    setView("library");
+    setIsOpen(true);
+  }, []);
+
+  const active = tabs.find((t) => t.id === activeId) ?? null;
+
+  return {
+    tabs,
+    active,
+    activeEntry: active ? (cache[active.id] ?? { status: "loading" as const }) : null,
+    isOpen,
+    view,
+    setView,
+    open,
+    close,
+    retry,
+    expand,
+    collapse,
+    showLibrary,
+  };
+}
+
+export type ArtifactPanelState = ReturnType<typeof useArtifactPanel>;
diff --git a/raggr-frontend/src/hooks/useChat.ts b/raggr-frontend/src/hooks/useChat.ts
index 1d61a3d..9ff489a 100644
--- a/raggr-frontend/src/hooks/useChat.ts
+++ b/raggr-frontend/src/hooks/useChat.ts
@@ -1,34 +1,44 @@
 import { useState, useCallback, useEffect, useRef } from "react";
 import { useMatch } from "react-router-dom";
-import { conversationService } from "../api/conversationService";
+import {
+  conversationService,
+  UploadError,
+  type ToolInput,
+} from "../api/conversationService";
+import type { ArtifactRef } from "../api/artifactTypes";
+import { validateAttachment, withAttachedFile } from "../lib/attachments";
 import type { Conversation } from "./useConversations";
 
-type Message = {
+export type ToolStatus = "running" | "ok" | "error";
+
+export type ToolMessage = {
+  speaker: "tool";
+  run_id: string;
+  tool: string;
+  label: string;
+  input?: ToolInput;
+  status: ToolStatus;
+  ms?: number;
+  artifact?: ArtifactRef | null;
+  // Client-side wall-clock bounds, used for the timeline's total duration.
+  startedAt?: number;
+  endedAt?: number;
+  // Synthesised run_id for a server that sends no run_id; such a row pairs
+  // with the next tool_end for the same tool.
+  legacy?: boolean;
+};
+
+export type TextMessage = {
+  speaker: "simba" | "user";
   text: string;
-  speaker: "simba" | "user" | "tool";
   image_key?: string | null;
 };
 
-const TOOL_MESSAGES: Record<string, string> = {
-  simba_search: "Searching Simba's records...",
-  web_search: "Searching the web...",
-  get_current_date: "Checking today's date...",
-  ynab_budget_summary: "Checking budget summary...",
-  ynab_account_balances: "Checking account balances...",
-  ynab_search_transactions: "Looking up transactions...",
-  ynab_spending_report: "Adding up spending...",
-  ynab_category_budget: "Checking category budgets...",
-  ynab_recent_changes: "Checking recent budget changes...",
-  ynab_sql: "Querying budget data...",
-  obsidian_search_notes: "Searching notes...",
-  obsidian_read_note: "Reading note...",
-  obsidian_create_note: "Saving note...",
-  obsidian_create_task: "Creating task...",
-  journal_get_today: "Reading today's journal...",
-  journal_get_tasks: "Getting tasks...",
-  journal_add_task: "Adding task...",
-  journal_complete_task: "Completing task...",
-};
+export type Message = TextMessage | ToolMessage;
+
+const fallbackLabel = (tool: string) => `Using ${tool}…`;
+
+let legacyRunCounter = 0;
 
 const simbaAnswers = ["meow.", "hiss...", "purrrrrr", "yowOWROWWowowr"];
 
@@ -37,6 +47,8 @@ type UseChatOptions = {
   refreshConversations: () => Promise<void>;
   onSessionExpired: () => void;
   scrollToBottom: () => void;
+  /** Called when a tool in the streaming turn produced an artifact. */
+  onArtifact?: (ref: ArtifactRef, conversationId: string) => void;
 };
 
 export function useChat({
@@ -44,6 +56,7 @@ export function useChat({
   refreshConversations,
   onSessionExpired,
   scrollToBottom,
+  onArtifact,
 }: UseChatOptions) {
   // ChatScreen renders under a single catch-all route so it isn't remounted
   // when the first message navigates to /c/:id (which would abort the stream),
@@ -52,7 +65,9 @@ export function useChat({
   const [messages, setMessages] = useState<Message[]>([]);
   const [isLoading, setIsLoading] = useState(false);
   const [messagesLoading, setMessagesLoading] = useState(false);
-  const [pendingImage, setPendingImage] = useState<File | null>(null);
+  // One image or text-like file to send with the next message.
+  const [pendingAttachment, setPendingAttachment] = useState<File | null>(null);
+  const [attachmentError, setAttachmentError] = useState<string | null>(null);
   const [error, setError] = useState<string | null>(null);
   const [stalled, setStalled] = useState(false);
   const [streaming, setStreaming] = useState(false);
@@ -61,6 +76,8 @@ export function useChat({
   const [thinkingDurationMs, setThinkingDurationMs] = useState<number | null>(null);
 
   const stalledQueryRef = useRef<string | null>(null);
+  const onArtifactRef = useRef(onArtifact);
+  onArtifactRef.current = onArtifact;
   const thinkingStartRef = useRef<number | null>(null);
 
   const isMountedRef = useRef(true);
@@ -117,11 +134,22 @@ export function useChat({
         const fetched = await conversationService.getConversation(conversationId);
         if (cancelled) return;
         setMessages(
-          (fetched.messages ?? []).map((m) => ({
-            text: m.text,
-            speaker: m.speaker,
-            image_key: m.image_key,
-          })),
+          (fetched.messages ?? []).map((m): Message => {
+            if (m.speaker === "tool") {
+              // Saved tool messages carry no input, status or duration.
+              // Pre-v2 servers send only the "[<tool> result]" header line.
+              const tool = m.tool ?? m.text.match(/^\[(\S+) result\]/)?.[1] ?? "";
+              return {
+                speaker: "tool",
+                run_id: m.id,
+                tool,
+                label: m.label ?? (tool ? fallbackLabel(tool) : "Used a tool"),
+                status: "ok",
+                artifact: m.artifact ?? null,
+              };
+            }
+            return { text: m.text, speaker: m.speaker, image_key: m.image_key };
+          }),
         );
         scrollToBottom();
       } catch (err) {
@@ -140,7 +168,7 @@ export function useChat({
 
   const sendMessage = useCallback(
     async (query: string, simbaMode: boolean) => {
-      if ((!query.trim() && !pendingImage) || isLoading) return;
+      if ((!query.trim() && !pendingAttachment) || isLoading) return;
 
       let activeId = conversationId;
       if (!activeId) {
@@ -150,7 +178,7 @@ export function useChat({
         activeId = created.id;
       }
 
-      const imageFile = pendingImage;
+      const attachment = pendingAttachment;
 
       setError(null);
       setStalled(false);
@@ -161,7 +189,8 @@ export function useChat({
       streamingActiveRef.current = false;
       setStreaming(false);
       updateMessages((prev) => prev.concat([{ text: query, speaker: "user" }]));
-      setPendingImage(null);
+      setPendingAttachment(null);
+      setAttachmentError(null);
       setIsLoading(true);
 
       if (simbaMode) {
@@ -179,18 +208,27 @@ export function useChat({
 
       try {
         let imageKey: string | undefined;
-        if (imageFile) {
-          const uploadResult = await conversationService.uploadImage(
-            imageFile,
+        let fileKey: string | undefined;
+        if (attachment) {
+          const uploadResult = await conversationService.uploadAttachment(
+            attachment,
             activeId,
           );
-          imageKey = uploadResult.image_key;
+          let patch: Partial<TextMessage>;
+          if (uploadResult.kind === "image") {
+            imageKey = uploadResult.image_key;
+            patch = { image_key: imageKey };
+          } else {
+            fileKey = uploadResult.file_key;
+            patch = { text: withAttachedFile(query, uploadResult.name) };
+          }
 
           updateMessages((prev) => {
             const updated = [...prev];
             for (let i = updated.length - 1; i >= 0; i--) {
-              if (updated[i].speaker === "user") {
-                updated[i] = { ...updated[i], image_key: imageKey };
+              const msg = updated[i];
+              if (msg.speaker === "user") {
+                updated[i] = { ...msg, ...patch };
                 break;
               }
             }
@@ -214,11 +252,56 @@ export function useChat({
               // Any text after a tool call belongs in a fresh bubble.
               streamingActiveRef.current = false;
               setThinking(false);
-              const friendly =
-                TOOL_MESSAGES[event.tool] ?? `Using ${event.tool}...`;
-              updateMessages((prev) =>
-                prev.concat([{ text: friendly, speaker: "tool" }]),
-              );
+              const legacy = !event.run_id;
+              const row: ToolMessage = {
+                speaker: "tool",
+                run_id: event.run_id ?? `legacy-${++legacyRunCounter}`,
+                tool: event.tool,
+                label: event.label ?? fallbackLabel(event.tool),
+                input: event.input,
+                status: "running",
+                startedAt: Date.now(),
+                legacy,
+              };
+              updateMessages((prev) => prev.concat([row]));
+            } else if (event.type === "tool_end") {
+              if (event.artifact) onArtifactRef.current?.(event.artifact, activeId);
+              const now = Date.now();
+              updateMessages((prev) => {
+                // Pair by run_id; a legacy end (no run_id) pairs with the
+                // oldest still-running legacy row for the same tool.
+                const idx = prev.findIndex((m) =>
+                  m.speaker === "tool" &&
+                  (event.run_id
+                    ? m.run_id === event.run_id
+                    : m.legacy && m.status === "running" && m.tool === event.tool),
+                );
+                const ended = {
+                  status: event.status ?? "ok",
+                  artifact: event.artifact ?? null,
+                  endedAt: now,
+                } as const;
+                if (idx === -1) {
+                  // End without a matching start: show it as a finished row.
+                  return prev.concat([{
+                    speaker: "tool",
+                    run_id: event.run_id ?? `legacy-${++legacyRunCounter}`,
+                    tool: event.tool,
+                    label: event.label ?? fallbackLabel(event.tool),
+                    ms: event.ms,
+                    ...ended,
+                  }]);
+                }
+                const row = prev[idx] as ToolMessage;
+                const updated = [...prev];
+                updated[idx] = {
+                  ...row,
+                  ...ended,
+                  label: event.label ?? row.label,
+                  ms: event.ms ?? (row.startedAt != null ? now - row.startedAt : undefined),
+                };
+                return updated;
+              });
             } else if (event.type === "content") {
               setThinking(false);
               if (thinkingStartRef.current !== null && thinkingDurationMs === null) {
@@ -228,6 +311,7 @@ export function useChat({
                 updateMessages((prev) => {
                   const updated = [...prev];
                   const last = updated[updated.length - 1];
+                  if (last.speaker === "tool") return prev;
                   updated[updated.length - 1] = {
                     ...last,
                     text: last.text + event.delta,
@@ -247,10 +331,9 @@ export function useChat({
               if (streamingActiveRef.current) {
                 updateMessages((prev) => {
                   const updated = [...prev];
-                  updated[updated.length - 1] = {
-                    ...updated[updated.length - 1],
-                    text: event.message,
-                  };
+                  const last = updated[updated.length - 1];
+                  if (last.speaker === "tool") return prev;
+                  updated[updated.length - 1] = { ...last, text: event.message };
                   return updated;
                 });
                 streamingActiveRef.current = false;
@@ -272,10 +355,13 @@ export function useChat({
           },
           abortController.signal,
           imageKey,
+          fileKey,
         );
       } catch (err) {
         if (err instanceof Error && err.name === "AbortError") {
           // User cancelled — not an error to surface.
+        } else if (err instanceof UploadError) {
+          if (isMountedRef.current) setError(`Couldn't attach that file: ${err.message}`);
         } else {
           console.error("Failed to send query:", err);
           if (
@@ -289,6 +375,17 @@ export function useChat({
         }
       } finally {
         if (isMountedRef.current) {
+          // A stream that ends (or is cancelled) mid-call leaves rows that
+          // will never get a tool_end; stop their spinners.
+          setMessages((prev) =>
+            prev.some((m) => m.speaker === "tool" && m.status === "running")
+              ? prev.map((m) =>
+                  m.speaker === "tool" && m.status === "running"
+                    ? { ...m, status: "error", endedAt: Date.now() }
+                    : m,
+                )
+              : prev,
+          );
           setIsLoading(false);
           setStreaming(false);
           setThinking(false);
@@ -302,7 +399,7 @@ export function useChat({
       }
     },
     [
-      pendingImage,
+      pendingAttachment,
       isLoading,
       conversationId,
       createConversation,
@@ -319,6 +416,19 @@ export function useChat({
 
   const clearError = useCallback(() => setError(null), []);
 
+  const attachFile = useCallback((file: File) => {
+    const problem = validateAttachment(file);
+    setAttachmentError(problem);
+    if (!problem) setPendingAttachment(file);
+  }, []);
+
+  const clearAttachment = useCallback(() => {
+    setPendingAttachment(null);
+    setAttachmentError(null);
+  }, []);
+
+  const clearAttachmentError = useCallback(() => setAttachmentError(null), []);
+
   const retryStalled = useCallback(() => {
     const q = stalledQueryRef.current;
     if (!q) return;
@@ -334,8 +444,11 @@ export function useChat({
     streaming,
     thinking,
     messagesLoading,
-    pendingImage,
-    setPendingImage,
+    pendingAttachment,
+    attachFile,
+    clearAttachment,
+    attachmentError,
+    clearAttachmentError,
     sendMessage,
     stopGeneration,
     error,
diff --git a/raggr-frontend/src/lib/attachments.ts b/raggr-frontend/src/lib/attachments.ts
new file mode 100644
index 0000000..8f8c1bb
--- /dev/null
+++ b/raggr-frontend/src/lib/attachments.ts
@@ -0,0 +1,63 @@
+// What can be attached to a message: images go to the vision model, text-like
+// files are extracted server-side and appended to the turn.
+
+export const ATTACHMENT_ACCEPT = "image/*,.pdf,.txt,.md,.markdown,.csv";
+export const MAX_ATTACHMENT_BYTES = 10 * 1024 * 1024;
+
+const IMAGE_TYPES = new Set([
+  "image/jpeg",
+  "image/png",
+  "image/webp",
+  "image/heic",
+  "image/heif",
+]);
+const FILE_EXTENSIONS = new Set(["pdf", "txt", "md", "markdown", "csv"]);
+const FILE_TYPES = new Set([
+  "application/pdf",
+  "text/plain",
+  "text/markdown",
+  "text/x-markdown",
+  "text/csv",
+]);
+
+export type AttachmentKind = "image" | "file";
+
+export const fileExtension = (name: string) =>
+  name.includes(".") ? name.split(".").pop()!.toLowerCase() : "";
+
+export function attachmentKind(file: File): AttachmentKind | null {
+  if (IMAGE_TYPES.has(file.type)) return "image";
+  if (FILE_TYPES.has(file.type) || FILE_EXTENSIONS.has(fileExtension(file.name))) {
+    return "file";
+  }
+  return null;
+}
+
+/** Returns an error message if the file can't be attached, else null. */
+export function validateAttachment(file: File): string | null {
+  if (!attachmentKind(file)) {
+    return `Can't attach “${file.name}”. Use an image, PDF, TXT, MD or CSV file.`;
+  }
+  if (file.size > MAX_ATTACHMENT_BYTES) {
+    return `“${file.name}” is larger than 10 MB.`;
+  }
+  return null;
+}
+
+export function formatBytes(bytes: number): string {
+  if (bytes < 1024) return `${bytes} B`;
+  if (bytes < 1024 * 1024) return `${Math.round(bytes / 1024)} KB`;
+  return `${(bytes / (1024 * 1024)).toFixed(1)} MB`;
+}
+
+// Saved user messages record an attached file as a trailing "📎 name" line.
+const ATTACHED_FILE_RE = /(?:^|\n\n)📎 ([^\n]+)$/u;
+
+export const withAttachedFile = (text: string, name: string) =>
+  text ? `${text}\n\n📎 ${name}` : `📎 ${name}`;
+
+export function splitAttachedFile(text: string): { body: string; fileName: string | null } {
+  const match = text.match(ATTACHED_FILE_RE);
+  if (!match) return { body: text, fileName: null };
+  return { body: text.slice(0, match.index), fileName: match[1] };
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/mealie.meal_plan.json b/raggr-frontend/test-fixtures/cowork/artifacts/mealie.meal_plan.json
new file mode 100644
index 0000000..e6616bf
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/mealie.meal_plan.json
@@ -0,0 +1,90 @@
+{
+  "kind": "mealie.meal_plan",
+  "title": "Meal plan · Oct 12–18",
+  "data": {
+    "start_date": "2026-10-12",
+    "end_date": "2026-10-18",
+    "days": [
+      {
+        "date": "2026-10-12",
+        "meals": [
+          {
+            "entry_type": "breakfast",
+            "name": "Overnight oats",
+            "recipe_slug": "overnight-oats"
+          },
+          {
+            "entry_type": "dinner",
+            "name": "Chicken Tikka Masala",
+            "recipe_slug": "chicken-tikka-masala"
+          }
+        ]
+      },
+      {
+        "date": "2026-10-13",
+        "meals": [
+          {
+            "entry_type": "dinner",
+            "name": "Leftovers",
+            "note": "Tikka masala + extra rice"
+          }
+        ]
+      },
+      {
+        "date": "2026-10-14",
+        "meals": [
+          {
+            "entry_type": "lunch",
+            "name": "Lentil soup",
+            "recipe_slug": "lentil-soup"
+          },
+          {
+            "entry_type": "dinner",
+            "name": "Sheet-pan gnocchi",
+            "recipe_slug": "sheet-pan-gnocchi"
+          }
+        ]
+      },
+      {
+        "date": "2026-10-16",
+        "meals": [
+          {
+            "entry_type": "dinner",
+            "name": "Taco night",
+            "note": "Pick up tortillas"
+          },
+          {
+            "entry_type": "side",
+            "name": "Elote salad",
+            "recipe_slug": "elote-salad"
+          }
+        ]
+      },
+      {
+        "date": "2026-10-17",
+        "meals": [
+          {
+            "entry_type": "dinner",
+            "name": "Dinner out",
+            "note": "Burma Superstar 7pm"
+          }
+        ]
+      },
+      {
+        "date": "2026-10-18",
+        "meals": [
+          {
+            "entry_type": "breakfast",
+            "name": "Dutch baby",
+            "recipe_slug": "dutch-baby"
+          },
+          {
+            "entry_type": "dinner",
+            "name": "Mushroom risotto",
+            "recipe_slug": "mushroom-risotto"
+          }
+        ]
+      }
+    ]
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/mealie.recipe.json b/raggr-frontend/test-fixtures/cowork/artifacts/mealie.recipe.json
new file mode 100644
index 0000000..baf037f
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/mealie.recipe.json
@@ -0,0 +1,56 @@
+{
+  "kind": "mealie.recipe",
+  "title": "Chicken Tikka Masala",
+  "source_ref": {
+    "system": "mealie",
+    "id": "chicken-tikka-masala",
+    "url": "https://mealie.example.lan/g/home/r/chicken-tikka-masala"
+  },
+  "data": {
+    "slug": "chicken-tikka-masala",
+    "name": "Chicken Tikka Masala",
+    "description": "Weeknight tikka masala with yogurt-marinated chicken thighs and a creamy tomato sauce.",
+    "servings": "4 servings",
+    "prep_time": "20 minutes",
+    "cook_time": "35 minutes",
+    "total_time": "55 minutes",
+    "ingredients": [
+      "1.5 lb boneless chicken thighs, cut into chunks",
+      "1 cup plain whole-milk yogurt",
+      "2 tbsp garam masala, divided",
+      "1 tbsp lemon juice",
+      "2 tbsp ghee or neutral oil",
+      "1 large onion, finely diced",
+      "4 cloves garlic, minced",
+      "1 tbsp grated ginger",
+      "1 can (28 oz) crushed tomatoes",
+      "3/4 cup heavy cream",
+      "1 tsp kosher salt",
+      "Cilantro and basmati rice, to serve"
+    ],
+    "instructions": [
+      {
+        "title": "Marinate",
+        "text": "Mix the yogurt, 1 tbsp garam masala, lemon juice and salt. Toss with the chicken and rest at least 15 minutes."
+      },
+      {
+        "text": "Broil the chicken on a sheet pan for 8–10 minutes until charred at the edges."
+      },
+      {
+        "title": "Sauce",
+        "text": "Melt the ghee in a large pan. Cook the onion until golden, about 8 minutes, then add the garlic, ginger and the rest of the garam masala for 1 minute."
+      },
+      {
+        "text": "Add the tomatoes and simmer 15 minutes. Stir in the cream and the chicken and simmer 5 more minutes."
+      },
+      {
+        "text": "Finish with cilantro and serve over rice."
+      }
+    ],
+    "tags": [
+      "Indian",
+      "Weeknight",
+      "Freezer friendly"
+    ]
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/mealie.shopping_lists.json b/raggr-frontend/test-fixtures/cowork/artifacts/mealie.shopping_lists.json
new file mode 100644
index 0000000..4f9cbe0
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/mealie.shopping_lists.json
@@ -0,0 +1,67 @@
+{
+  "kind": "mealie.shopping_lists",
+  "title": "Shopping lists",
+  "data": {
+    "lists": [
+      {
+        "name": "Groceries",
+        "items": [
+          {
+            "name": "Chicken thighs",
+            "quantity": 1.5,
+            "checked": false
+          },
+          {
+            "name": "Crushed tomatoes (28 oz)",
+            "quantity": 1.0,
+            "checked": false
+          },
+          {
+            "name": "Heavy cream",
+            "quantity": 1.0,
+            "checked": false
+          },
+          {
+            "name": "Tortillas",
+            "quantity": 2.0,
+            "checked": false
+          },
+          {
+            "name": "Whole-milk yogurt",
+            "quantity": 1.0,
+            "checked": true
+          },
+          {
+            "name": "Cilantro",
+            "quantity": 1.0,
+            "checked": true
+          }
+        ]
+      },
+      {
+        "name": "Costco",
+        "items": [
+          {
+            "name": "Cat litter",
+            "quantity": 2.0,
+            "checked": false
+          },
+          {
+            "name": "Olive oil",
+            "quantity": 1.0,
+            "checked": false
+          },
+          {
+            "name": "Paper towels",
+            "quantity": 1.0,
+            "checked": true
+          }
+        ]
+      },
+      {
+        "name": "Pet store",
+        "items": []
+      }
+    ]
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/obsidian.note.json b/raggr-frontend/test-fixtures/cowork/artifacts/obsidian.note.json
new file mode 100644
index 0000000..959234a
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/obsidian.note.json
@@ -0,0 +1,24 @@
+{
+  "kind": "obsidian.note",
+  "title": "2026-09 annual checkup",
+  "source_ref": {
+    "system": "obsidian",
+    "path": "Simba/Vet/2026-09 annual checkup.md",
+    "url": "obsidian://open?vault=Home&file=Simba%2FVet%2F2026-09%20annual%20checkup.md"
+  },
+  "data": {
+    "path": "Simba/Vet/2026-09 annual checkup.md",
+    "title": "2026-09 annual checkup",
+    "tags": [
+      "simba",
+      "vet",
+      "health"
+    ],
+    "frontmatter": {
+      "date": "2026-09-18",
+      "vet": "Mission Pet Hospital",
+      "weight_lb": 11.4
+    },
+    "markdown": "# Annual checkup\n\n**Vet:** Dr. Patel, Mission Pet Hospital  \n**Weight:** 11.4 lb (down from 11.9)\n\n## Notes\n\n- Teeth look good; mild tartar on the upper molars.\n- Weight loss is fine, but keep an eye on it. Re-weigh in 3 months.\n- Vaccines: FVRCP booster given. Rabies is due **2027-03**.\n\n## Follow-ups\n\n- [x] Book dental cleaning quote\n- [ ] Switch to the weight-management kibble\n- [ ] Re-weigh in December\n\n| Item | Cost |\n|---|---|\n| Exam | $72.00 |\n| FVRCP | $38.00 |\n| **Total** | **$110.00** |\n\n> Simba was a perfect gentleman until the thermometer.\n"
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/search.documents.json b/raggr-frontend/test-fixtures/cowork/artifacts/search.documents.json
new file mode 100644
index 0000000..2c3a4ed
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/search.documents.json
@@ -0,0 +1,31 @@
+{
+  "kind": "search.documents",
+  "title": "Search: Simba vaccination records",
+  "data": {
+    "query": "Simba vaccination records",
+    "source": "paperless",
+    "results": [
+      {
+        "title": "2026-09-18_mission-pet-hospital",
+        "snippet": "Patient: Simba (feline, DSH, M/N). Services: annual wellness exam, FVRCP vaccine (3-year), fecal test. Next due: rabies 03/2027. Total $110.00.",
+        "filename": "2026-09-18_mission-pet-hospital.pdf",
+        "document_type": "Invoice",
+        "date": "2026-09-18"
+      },
+      {
+        "title": "rabies-certificate-2024",
+        "snippet": "This certifies that Simba has been vaccinated against rabies. Vaccine: Purevax Feline Rabies, lot 3K91A. Date given 03/14/2024. Expires 03/14/2027.",
+        "filename": "rabies-certificate-2024.pdf",
+        "document_type": "Certificate",
+        "date": "2024-03-14"
+      },
+      {
+        "title": "2022-05-09_sf-spca-adoption",
+        "snippet": "Simba, approx. 10 weeks. Vaccines given: FVRCP #1 (2022-05-02), deworming. Microchip 985112004567213 registered to adopter.",
+        "filename": "2022-05-09_sf-spca-adoption.pdf",
+        "document_type": "Pet records",
+        "date": "2022-05-09"
+      }
+    ]
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/ynab.category_budget.json b/raggr-frontend/test-fixtures/cowork/artifacts/ynab.category_budget.json
new file mode 100644
index 0000000..fad40cb
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/ynab.category_budget.json
@@ -0,0 +1,105 @@
+{
+  "kind": "ynab.category_budget",
+  "title": "Category budget · October 2026",
+  "data": {
+    "month": "2026-10",
+    "groups": [
+      {
+        "name": "Bills",
+        "categories": [
+          {
+            "name": "Rent",
+            "assigned": 2400.0,
+            "activity": -2400.0,
+            "available": 0.0,
+            "goal_target": 2400.0
+          },
+          {
+            "name": "Electric",
+            "assigned": 120.0,
+            "activity": -84.31,
+            "available": 35.69
+          },
+          {
+            "name": "Internet",
+            "assigned": 70.0,
+            "activity": -70.0,
+            "available": 0.0,
+            "goal_target": 70.0
+          },
+          {
+            "name": "Phone",
+            "assigned": 85.0,
+            "activity": 0.0,
+            "available": 85.0
+          }
+        ]
+      },
+      {
+        "name": "Everyday",
+        "categories": [
+          {
+            "name": "Groceries",
+            "assigned": 650.0,
+            "activity": -412.88,
+            "available": 237.12,
+            "goal_target": 650.0
+          },
+          {
+            "name": "Dining Out",
+            "assigned": 200.0,
+            "activity": -286.42,
+            "available": -86.42
+          },
+          {
+            "name": "Transportation",
+            "assigned": 180.0,
+            "activity": -61.2,
+            "available": 118.8
+          }
+        ]
+      },
+      {
+        "name": "Simba",
+        "categories": [
+          {
+            "name": "Pet Food",
+            "assigned": 90.0,
+            "activity": -64.99,
+            "available": 25.01
+          },
+          {
+            "name": "Pet Care",
+            "assigned": 60.0,
+            "activity": -83.1,
+            "available": -23.1
+          },
+          {
+            "name": "Litter",
+            "assigned": 40.0,
+            "activity": -18.49,
+            "available": 21.51
+          }
+        ]
+      },
+      {
+        "name": "Savings",
+        "categories": [
+          {
+            "name": "Emergency Fund",
+            "assigned": 500.0,
+            "activity": 0.0,
+            "available": 8250.0,
+            "goal_target": 10000.0
+          },
+          {
+            "name": "Vacation",
+            "assigned": 250.0,
+            "activity": 0.0,
+            "available": 1340.0
+          }
+        ]
+      }
+    ]
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/ynab.spending_report.json b/raggr-frontend/test-fixtures/cowork/artifacts/ynab.spending_report.json
new file mode 100644
index 0000000..72cb53d
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/ynab.spending_report.json
@@ -0,0 +1,57 @@
+{
+  "kind": "ynab.spending_report",
+  "title": "Spending by category · Sep 1–30",
+  "data": {
+    "start_date": "2026-09-01",
+    "end_date": "2026-09-30",
+    "group_by": "category",
+    "total": 3642.21,
+    "rows": [
+      {
+        "key": "Rent",
+        "amount": 2400.0,
+        "count": 1
+      },
+      {
+        "key": "Groceries",
+        "amount": 588.14,
+        "count": 14
+      },
+      {
+        "key": "Dining Out",
+        "amount": 243.7,
+        "count": 9
+      },
+      {
+        "key": "Pet Care",
+        "amount": 148.0,
+        "count": 2
+      },
+      {
+        "key": "Electric",
+        "amount": 97.55,
+        "count": 1
+      },
+      {
+        "key": "Transportation",
+        "amount": 74.32,
+        "count": 5
+      },
+      {
+        "key": "Internet",
+        "amount": 70.0,
+        "count": 1
+      },
+      {
+        "key": "Pet Food",
+        "amount": 62.5,
+        "count": 2
+      },
+      {
+        "key": "Clothing",
+        "amount": -42.0,
+        "count": 2
+      }
+    ]
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/ynab.summary.json b/raggr-frontend/test-fixtures/cowork/artifacts/ynab.summary.json
new file mode 100644
index 0000000..fa7fc5d
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/ynab.summary.json
@@ -0,0 +1,27 @@
+{
+  "kind": "ynab.summary",
+  "title": "Budget · October 2026",
+  "data": {
+    "month": "2026-10",
+    "ready_to_assign": 412.37,
+    "income": 7850.0,
+    "assigned": 7437.63,
+    "spent": 3921.48,
+    "age_of_money": 41,
+    "net_worth": 84213.92,
+    "overspent": [
+      {
+        "name": "Dining Out",
+        "available": -86.42
+      },
+      {
+        "name": "Pet Care",
+        "available": -23.1
+      },
+      {
+        "name": "Gifts",
+        "available": -5.99
+      }
+    ]
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/artifacts/ynab.transactions.json b/raggr-frontend/test-fixtures/cowork/artifacts/ynab.transactions.json
new file mode 100644
index 0000000..5a24b86
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/artifacts/ynab.transactions.json
@@ -0,0 +1,78 @@
+{
+  "kind": "ynab.transactions",
+  "title": "Transactions · Sep 12–Oct 12",
+  "data": {
+    "start_date": "2026-09-12",
+    "end_date": "2026-10-12",
+    "count": 9,
+    "total": -286.42,
+    "transactions": [
+      {
+        "date": "2026-10-10",
+        "payee": "Tartine Bakery",
+        "category": "Dining Out",
+        "account": "Chase Sapphire",
+        "amount": -18.75
+      },
+      {
+        "date": "2026-10-08",
+        "payee": "Burma Superstar",
+        "category": "Dining Out",
+        "account": "Chase Sapphire",
+        "memo": "Dinner with Alex",
+        "amount": -72.4
+      },
+      {
+        "date": "2026-10-05",
+        "payee": "Philz Coffee",
+        "category": "Dining Out",
+        "account": "Checking",
+        "amount": -6.25
+      },
+      {
+        "date": "2026-10-03",
+        "payee": "Souvla",
+        "category": "Dining Out",
+        "account": "Chase Sapphire",
+        "amount": -34.1
+      },
+      {
+        "date": "2026-09-30",
+        "payee": "Venmo",
+        "category": "Dining Out",
+        "account": "Checking",
+        "memo": "Split pizza refund",
+        "amount": 15.0
+      },
+      {
+        "date": "2026-09-27",
+        "payee": "Zuni Cafe",
+        "category": "Dining Out",
+        "account": "Chase Sapphire",
+        "memo": "Anniversary",
+        "amount": -121.32
+      },
+      {
+        "date": "2026-09-22",
+        "payee": "Philz Coffee",
+        "category": "Dining Out",
+        "account": "Checking",
+        "amount": -6.25
+      },
+      {
+        "date": "2026-09-18",
+        "payee": "Golden Boy Pizza",
+        "category": "Dining Out",
+        "account": "Chase Sapphire",
+        "amount": -29.6
+      },
+      {
+        "date": "2026-09-14",
+        "payee": "Tartine Bakery",
+        "category": "Dining Out",
+        "account": "Chase Sapphire",
+        "amount": -12.75
+      }
+    ]
+  }
+}
diff --git a/raggr-frontend/test-fixtures/cowork/mock-server.mjs b/raggr-frontend/test-fixtures/cowork/mock-server.mjs
new file mode 100644
index 0000000..434ca17
--- /dev/null
+++ b/raggr-frontend/test-fixtures/cowork/mock-server.mjs
@@ -0,0 +1,679 @@
+#!/usr/bin/env node
+// Dependency-free mock of the SimbaRAG API for frontend work on the Cowork UI.
+// Speaks the contract in docs/cowork-ui-plan.md: serves dist/ with an SPA
+// catch-all, stubs auth + conversation CRUD + artifacts, and streams
+// contract-shaped SSE from /api/conversation/stream-query.
+//
+//   yarn build && node test-fixtures/cowork/mock-server.mjs [port]
+//
+// Seed localStorage access_token/refresh_token with any value to get past
+// the auth gate. The stream scenario is picked by a keyword in the query:
+//   "parallel" two interleaved calls, one with an artifact
+//   "error"    a call that fails, then an answer
+//   "legacy"   old-server events: {type:"tool_start",tool} / {type:"tool_end",tool}
+//   "plain"    no tools, just a streamed answer
+//   artifact panel scenarios, one tool call each with that kind's fixture:
+//     "recipe" | "meal" | "shopping" | "note" | "vaccin" (search.documents) |
+//     "budget" (summary + category budget, newest wins) | "by category"
+//     (spending report) | "trend" (month-grouped spending) | "transactions" |
+//     "philz" (open-ended transactions, start_date null) | "everything"
+//     (all v1 kinds) | "broken" (GET /api/artifacts/<id> 500s) | "mystery"
+//     (unknown kind → JSON fallback)
+//   anything else: two sequential calls, then a streamed answer
+//   any query sent with a file_key: reads the attached file (by name)
+// Conversations "seeded" (timeline), "everything" (one saved tool message
+// per artifact kind) and "attachment" (a saved 📎 file message) exist up front.
+//
+// Uploads (POST /api/conversation/upload) follow the contract: JPEG/PNG/WebP/
+// HEIC -> {kind:"image"}, PDF/TXT/MD/CSV (by MIME or extension) ->
+// {kind:"file"}, anything else 415, files named *scan*.pdf 422 (no text
+// layer). Uploaded images are served back via /api/conversation/image/<key>.
+// GET /__mock/requests returns recorded API request bodies (multipart files
+// summarised as {filename, type, size}), newest last.
+// artifacts/<kind>.json holds one ToolArtifact per v1 kind, matching what the
+// backend tools emit. Any other *.json in this directory with `kind` and
+// `data` is loaded as an artifact of "seeded" (`id` defaults to the file name).
+// MOCK_DELAY_SCALE=0.2 speeds the stream up; 0 makes it instant.
+
+import http from "node:http";
+import fs from "node:fs";
+import path from "node:path";
+import crypto from "node:crypto";
+import { fileURLToPath } from "node:url";
+
+const here = path.dirname(fileURLToPath(import.meta.url));
+const distDir = path.resolve(here, "../../dist");
+const port = Number(process.argv[2] ?? process.env.PORT ?? 5173);
+const delayScale = Number(process.env.MOCK_DELAY_SCALE ?? 1);
+
+const MIME = {
+  ".html": "text/html; charset=utf-8",
+  ".js": "text/javascript",
+  ".css": "text/css",
+  ".json": "application/json",
+  ".png": "image/png",
+  ".jpg": "image/jpeg",
+  ".jpeg": "image/jpeg",
+  ".svg": "image/svg+xml",
+  ".ico": "image/x-icon",
+  ".woff2": "font/woff2",
+  ".webmanifest": "application/manifest+json",
+};
+
+const now = () => new Date().toISOString();
+const sleep = (ms) => new Promise((r) => setTimeout(r, ms * delayScale));
+const uuid = () => crypto.randomUUID();
+
+// ---------------------------------------------------------------- state
+
+/** @type {Map<string, any>} full Artifact records by id */
+const artifacts = new Map();
+/** @type {Map<string, {id, name, created_at, updated_at, messages: any[]}>} */
+const conversations = new Map();
+/** Uploaded objects by S3-style key: {bytes, type, name} */
+const blobs = new Map();
+/** Recorded API requests: {method, path, body} */
+const requests = [];
+
+function addArtifact(conversationId, tool, a) {
+  const record = {
+    id: a.id ?? uuid(),
+    kind: a.kind,
+    title: a.title,
+    data: a.data ?? {},
+    source_ref: a.source_ref ?? null,
+    tool: a.tool ?? tool,
+    conversation_id: conversationId,
+    message_id: a.message_id ?? null,
+    created_at: a.created_at ?? now(),
+  };
+  if (a.broken) record.broken = true; // GET /api/artifacts/<id> answers 500
+  artifacts.set(record.id, record);
+  return record;
+}
+
+const refOf = (a) => (a ? { id: a.id, kind: a.kind, title: a.title } : null);
+
+// Spending amounts are positive (-SUM of outflows), as the backend sends them.
+const SPENDING = {
+  kind: "ynab.spending_report",
+  title: "Spending by category · Oct 1–12",
+  data: {
+    start_date: "2026-10-01",
+    end_date: "2026-10-12",
+    group_by: "category",
+    rows: [
+      { key: "Groceries", amount: 412.18, count: 9 },
+      { key: "Dining Out", amount: 186.4, count: 6 },
+      { key: "Cat Supplies", amount: 74.99, count: 2 },
+    ],
+    total: 673.57,
+  },
+};
+
+const RECIPE = {
+  kind: "mealie.recipe",
+  title: "Miso Salmon",
+  data: {
+    slug: "miso-salmon",
+    name: "Miso Salmon",
+    description: "Weeknight salmon glazed with white miso.",
+    servings: 2,
+    prep_time: "10 min",
+    cook_time: "12 min",
+    total_time: "22 min",
+    ingredients: ["2 salmon fillets", "2 tbsp white miso", "1 tbsp mirin"],
+    instructions: [{ text: "Whisk the glaze." }, { text: "Broil 10–12 minutes." }],
+    tags: ["dinner", "fish"],
+  },
+  source_ref: { system: "mealie", id: "miso-salmon" },
+};
+
+function newConversation(id = uuid(), name = "New Conversation") {
+  const c = { id, name, created_at: now(), updated_at: now(), messages: [] };
+  conversations.set(id, c);
+  return c;
+}
+
+function pushMessage(c, msg) {
+  const m = { id: uuid(), created_at: now(), image_key: null, ...msg };
+  c.messages.push(m);
+  c.updated_at = now();
+  return m;
+}
+
+// Saved tool messages as GET /api/conversation/<id> returns them: the header
+// line in `text`, plus tool/label/artifact.
+function seed() {
+  const c = newConversation("seeded", "Budget check (seeded)");
+  pushMessage(c, { speaker: "user", text: "How much did we spend on food this month?" });
+  const spend = addArtifact(c.id, "ynab_spending_report", SPENDING);
+  pushMessage(c, {
+    speaker: "tool",
+    text: "[get_current_date result]",
+    tool: "get_current_date",
+    label: "Checking today's date…",
+    artifact: null,
+  });
+  pushMessage(c, {
+    speaker: "tool",
+    text: "[ynab_spending_report result]",
+    tool: "ynab_spending_report",
+    label: "Building spending report…",
+    artifact: refOf(spend),
+  });
+  pushMessage(c, {
+    speaker: "simba",
+    text: "You've spent **$598.58** on food so far in October: $412.18 on groceries and $186.40 dining out.",
+  });
+  // A pre-v2 saved tool message: no tool/label/artifact fields at all.
+  pushMessage(c, { speaker: "user", text: "Anything on the web about miso salmon?" });
+  pushMessage(c, { speaker: "tool", text: "[web_search result]" });
+  pushMessage(c, { speaker: "simba", text: "Plenty — broil it for 10–12 minutes." });
+}
+
+function loadFixtureArtifacts() {
+  for (const f of fs.readdirSync(here)) {
+    if (!f.endsWith(".json")) continue;
+    try {
+      const a = JSON.parse(fs.readFileSync(path.join(here, f), "utf8"));
+      if (a && a.kind && a.data) {
+        addArtifact(a.conversation_id ?? "seeded", a.tool ?? "fixture", {
+          id: path.basename(f, ".json"),
+          ...a,
+        });
+      }
+    } catch (err) {
+      console.warn(`skipping fixture ${f}: ${err.message}`);
+    }
+  }
+}
+
+// Per-kind fixtures (artifacts/<kind>.json) plus a few variants.
+const FIXTURES = {};
+for (const f of fs.readdirSync(path.join(here, "artifacts"))) {
+  if (!f.endsWith(".json")) continue;
+  const a = JSON.parse(fs.readFileSync(path.join(here, "artifacts", f), "utf8"));
+  FIXTURES[a.kind] = a;
+}
+
+const EXTRA_FIXTURES = {
+  spendingByMonth: {
+    kind: "ynab.spending_report",
+    title: "Spending by month · Jan 1–Oct 12",
+    data: {
+      start_date: "2026-01-01",
+      end_date: "2026-10-12",
+      group_by: "month",
+      total: 2381.94,
+      rows: [
+        { key: "2026-01", amount: 188.4, count: 7 },
+        { key: "2026-02", amount: 302.55, count: 11 },
+        { key: "2026-03", amount: 241.1, count: 8 },
+        { key: "2026-04", amount: 150.0, count: 5 },
+        { key: "2026-05", amount: 276.9, count: 9 },
+        { key: "2026-06", amount: 333.12, count: 12 },
+        { key: "2026-07", amount: 198.45, count: 6 },
+        { key: "2026-08", amount: 221.3, count: 8 },
+        { key: "2026-09", amount: 183.7, count: 7 },
+        { key: "2026-10", amount: 286.42, count: 9 },
+      ],
+    },
+  },
+  // Open-ended search (payee filter, no start date): start_date is null.
+  openEndedTransactions: {
+    kind: "ynab.transactions",
+    title: "Transactions · through 2026-10-12",
+    data: {
+      start_date: null,
+      end_date: "2026-10-12",
+      count: 3,
+      total: -18.75,
+      transactions: [
+        { date: "2026-10-05", payee: "Philz Coffee", category: "Dining Out", account: "Checking", amount: -6.25 },
+        { date: "2026-09-22", payee: "Philz Coffee", category: "Dining Out", account: "Checking", amount: -6.25 },
+        { date: "2026-08-30", payee: "Philz Coffee", category: "Dining Out", account: "Checking", memo: "Beans", amount: -6.25 },
+      ],
+    },
+  },
+  mystery: {
+    kind: "homebox.item",
+    title: "Cat tree (Homebox)",
+    data: { name: "Cat tree", location: "Living room", quantity: 1, labels: ["simba"] },
+  },
+};
+
+const TOOL_FOR_KIND = {
+  "mealie.recipe": "mealie_get_recipe",
+  "mealie.meal_plan": "mealie_meal_plans",
+  "mealie.shopping_lists": "mealie_shopping_lists",
+  "obsidian.note": "obsidian_read_note",
+  "search.documents": "simba_search",
+  "ynab.summary": "ynab_budget_summary",
+  "ynab.transactions": "ynab_search_transactions",
+  "ynab.spending_report": "ynab_spending_report",
+  "ynab.category_budget": "ynab_category_budget",
+};
+const toolFor = (a) => TOOL_FOR_KIND[a.kind] ?? "homebox_get_item";
+
+// A conversation holding one saved tool message per artifact kind, for the
+// panel's library and reload checks.
+function seedEverything() {
+  const c = newConversation("everything", "Everything Simba knows");
+  pushMessage(c, { speaker: "user", text: "Show me everything" });
+  let t = Date.parse("2026-10-12T15:00:00Z");
+  for (const fx of [...Object.values(FIXTURES), ...Object.values(EXTRA_FIXTURES)]) {
+    const tool = toolFor(fx);
+    const msg = pushMessage(c, { speaker: "tool", text: `[${tool} result]`, tool, label: label(tool), artifact: null });
+    const a = addArtifact(c.id, tool, { ...fx, message_id: msg.id, created_at: new Date((t += 60_000)).toISOString() });
+    msg.artifact = refOf(a);
+  }
+  pushMessage(c, { speaker: "simba", text: "Here's everything I could find — open any artifact from the panel." });
+}
+
+
+// ---------------------------------------------------------------- SSE scenarios
+
+const LABELS = {
+  get_current_date: "Checking today's date…",
+  ynab_spending_report: "Building spending report…",
+  mealie_get_recipe: "Opening recipe…",
+  obsidian_search_notes: "Searching notes…",
+  web_search: "Searching the web…",
+  simba_search: "Searching Simba's records…",
+  mealie_meal_plans: "Checking the meal plan…",
+  mealie_shopping_lists: "Checking shopping lists…",
+  obsidian_read_note: "Reading note…",
+  ynab_budget_summary: "Checking budget…",
+  ynab_search_transactions: "Looking up transactions…",
+  ynab_category_budget: "Checking category budgets…",
+};
+const label = (tool) => LABELS[tool] ?? `Using ${tool}…`;
+
+function seedAttachment() {
+  const c = newConversation("attachment", "Vet bill questions");
+  pushMessage(c, { speaker: "user", text: "How much was the dental cleaning?\n\n📎 vet-invoice-2026-09.pdf" });
+  pushMessage(c, { speaker: "simba", text: "The dental cleaning on the September invoice was **$412.50**." });
+}
+
+seed();
+seedEverything();
+seedAttachment();
+loadFixtureArtifacts();
+
+/** Artifact-panel scenarios: one tool call per artifact, by keyword. */
+function artifactScenario(q) {
+  if (q.includes("everything")) return Object.keys(TOOL_FOR_KIND).map((k) => FIXTURES[k]);
+  if (q.includes("broken")) return [{ ...FIXTURES["ynab.summary"], title: "Broken artifact", broken: true }];
+  if (q.includes("mystery")) return [EXTRA_FIXTURES.mystery];
+  if (q.includes("trend")) return [EXTRA_FIXTURES.spendingByMonth];
+  if (q.includes("philz")) return [EXTRA_FIXTURES.openEndedTransactions];
+  if (q.includes("budget")) return [FIXTURES["ynab.summary"], FIXTURES["ynab.category_budget"]];
+  if (q.includes("recipe")) return [FIXTURES["mealie.recipe"]];
+  if (q.includes("meal")) return [FIXTURES["mealie.meal_plan"]];
+  if (q.includes("shopping")) return [FIXTURES["mealie.shopping_lists"]];
+  if (q.includes("note")) return [FIXTURES["obsidian.note"]];
+  if (q.includes("vaccin")) return [FIXTURES["search.documents"]];
+  if (q.includes("by category")) return [FIXTURES["ynab.spending_report"]];
+  if (q.includes("transactions")) return [FIXTURES["ynab.transactions"]];
+  return null;
+}
+
+/**
+ * Each step is [delayMs, event | fn(ctx) => event]. Tool steps are expanded
+ * into contract-shaped events; ctx persists tool messages and artifacts.
+ */
+function scenario(query, file) {
+  const q = query.toLowerCase();
+  const answer = (text) =>
+    text.match(/\S+\s*/g).map((w) => [60, { type: "content", delta: w }]);
+
+  if (file) {
+    return [
+      [200, { type: "thinking_delta", delta: `Reading the attached ${file.name}…` }],
+      [300, { start: "f1", tool: "simba_search", input: { query: (query || file.name).slice(0, 200) } }],
+      [600, { end: "f1" }],
+      ...answer(`I read **${file.name}**. It looks like a vet invoice; the dental cleaning came to $412.50.`),
+    ];
+  }
+
+  if (q.includes("plain")) {
+    return [[300, { type: "thinking" }], ...answer("Meow. Nothing to look up for that one.")];
+  }
+  if (q.includes("legacy")) {
+    return [
+      [300, { type: "tool_start", tool: "web_search" }],
+      [1200, { type: "tool_end", tool: "web_search" }],
+      [200, { type: "tool_start", tool: "simba_search" }],
+      [900, { type: "tool_end", tool: "simba_search" }],
+      ...answer("An older server sent those tool events without run ids."),
+    ];
+  }
+  if (q.includes("parallel")) {
+    return [
+      [300, { start: "r1", tool: "ynab_spending_report", input: { start_date: "2026-10-01", end_date: "2026-10-12", group_by: "category" } }],
+      [80, { start: "r2", tool: "mealie_get_recipe", input: { slug: "miso-salmon" } }],
+      [900, { end: "r2", artifact: RECIPE }],
+      [1100, { end: "r1", artifact: SPENDING }],
+      ...answer("Food spending is **$598.58** this month, and I pulled up the miso salmon recipe for tonight."),
+    ];
+  }
+  if (q.includes("error")) {
+    return [
+      [300, { start: "e1", tool: "obsidian_search_notes", input: { query: "vet appointment", limit: 5 } }],
+      [800, { end: "e1", status: "error" }],
+      [200, { start: "e2", tool: "web_search", input: { query: "cat vet near me open sunday" } }],
+      [1000, { end: "e2" }],
+      ...answer("I couldn't search your notes, but a couple of vets nearby are open on Sundays."),
+    ];
+  }
+  const artifactsForQuery = artifactScenario(q);
+  if (artifactsForQuery) {
+    return [
+      [250, { type: "thinking" }],
+      ...artifactsForQuery.flatMap((fx, i) => [
+        [200, { start: `a${i}`, tool: toolFor(fx), input: { query: query.slice(0, 200) } }],
+        [500, { end: `a${i}`, artifact: fx }],
+      ]),
+      ...answer("Here's what I found. Let me know if you want more detail."),
+    ];
+  }
+  return [
+    [300, { type: "thinking" }],
+    [200, { type: "thinking_delta", delta: "Need today's date before the budget lookup." }],
+    [300, { start: "s1", tool: "get_current_date", input: {} }],
+    [400, { end: "s1" }],
+    [200, { start: "s2", tool: "ynab_spending_report", input: { month: "2026-10", group_by: "category", include_hidden_categories_with_a_long_name: true } }],
+    [1500, { end: "s2" }],
+    ...answer("You've spent **$598.58** on food so far in October: $412.18 on groceries and $186.40 dining out."),
+  ];
+}
+
+async function streamQuery(req, res, body) {
+  const c = conversations.get(body.conversation_id) ?? newConversation(body.conversation_id);
+  let saved = body.query ?? "";
+  let file = null;
+  if (body.file_key) {
+    file = blobs.get(body.file_key);
+    if (!body.file_key.startsWith(`conversations/${c.id}/files/`) || !file) {
+      return json(res, 400, { error: "invalid file_key" });
+    }
+    saved = `${saved}\n\n📎 ${file.name}`.trim();
+  }
+  pushMessage(c, { speaker: "user", text: saved, image_key: body.image_key ?? null });
+  if (c.name === "New Conversation") c.name = (body.query || file?.name || "Attachment").slice(0, 40);
+
+  res.writeHead(200, {
+    "Content-Type": "text/event-stream",
+    "Cache-Control": "no-cache",
+    Connection: "keep-alive",
+  });
+  let closed = false;
+  res.on("close", () => (closed = true));
+  const send = (event) => !closed && res.write(`data: ${JSON.stringify(event)}\n\n`);
+
+  const runs = new Map(); // key -> {run_id, tool, started}
+  let text = "";
+  for (const [delay, step] of scenario(body.query ?? "", file)) {
+    await sleep(delay);
+    if (closed) return;
+    if (step.start) {
+      const run = { run_id: uuid(), tool: step.tool, started: Date.now() };
+      runs.set(step.start, run);
+      send({ type: "tool_start", run_id: run.run_id, tool: run.tool, label: label(run.tool), input: step.input ?? {} });
+    } else if (step.end) {
+      const run = runs.get(step.end);
+      const status = step.status ?? "ok";
+      const msg = pushMessage(c, {
+        speaker: "tool",
+        text: `[${run.tool} result]`,
+        tool: run.tool,
+        label: label(run.tool),
+        artifact: null,
+      });
+      let ref = null;
+      if (step.artifact && status === "ok") {
+        ref = refOf(addArtifact(c.id, run.tool, { ...step.artifact, message_id: msg.id }));
+        msg.artifact = ref;
+      }
+      send({
+        type: "tool_end",
+        run_id: run.run_id,
+        tool: run.tool,
+        label: label(run.tool),
+        status,
+        ms: Date.now() - run.started,
+        artifact: ref,
+      });
+    } else {
+      if (step.type === "tool_end") {
+        pushMessage(c, { speaker: "tool", text: `[${step.tool} result]` });
+      }
+      if (step.type === "content") text += step.delta;
+      send(step);
+    }
+  }
+  pushMessage(c, { speaker: "simba", text });
+  send({ type: "response", message: text });
+  res.end("data: [DONE]\n\n");
+}
+
+// ---------------------------------------------------------------- HTTP
+
+const json = (res, status, body) => {
+  res.writeHead(status, { "Content-Type": "application/json" });
+  res.end(JSON.stringify(body));
+};
+
+async function readRaw(req) {
+  const chunks = [];
+  for await (const chunk of req) chunks.push(chunk);
+  return Buffer.concat(chunks);
+}
+
+/** Minimal multipart/form-data parser: {fields, files: {name: {filename, type, data}}}. */
+function parseMultipart(buf, contentType) {
+  const boundary = /boundary=(?:"([^"]+)"|([^;]+))/.exec(contentType ?? "");
+  const out = { fields: {}, files: {} };
+  if (!boundary) return out;
+  const delim = Buffer.from(`--${boundary[1] ?? boundary[2]}`);
+  let pos = buf.indexOf(delim);
+  while (pos !== -1) {
+    const start = pos + delim.length + 2; // skip CRLF
+    const next = buf.indexOf(delim, start);
+    if (next === -1) break;
+    const part = buf.subarray(start, next - 2); // strip trailing CRLF
+    const headerEnd = part.indexOf("\r\n\r\n");
+    const headers = part.subarray(0, headerEnd).toString("utf8");
+    const data = part.subarray(headerEnd + 4);
+    const name = /name="([^"]*)"/.exec(headers)?.[1];
+    const filename = /filename="([^"]*)"/.exec(headers)?.[1];
+    if (name && filename !== undefined) {
+      const type = /Content-Type:\s*([^\r\n]+)/i.exec(headers)?.[1]?.trim() ?? "";
+      out.files[name] = { filename, type, data };
+    } else if (name) {
+      out.fields[name] = data.toString("utf8");
+    }
+    pos = next;
+  }
+  return out;
+}
+
+/** Read the body once: JSON, or multipart form as {fields, files}. */
+async function readBody(req) {
+  const raw = await readRaw(req);
+  const type = req.headers["content-type"] ?? "";
+  if (type.startsWith("multipart/form-data")) return { form: parseMultipart(raw, type) };
+  try {
+    return raw.length ? JSON.parse(raw.toString("utf8")) : {};
+  } catch {
+    return {};
+  }
+}
+
+const IMAGE_TYPES = new Set(["image/jpeg", "image/png", "image/webp", "image/heic", "image/heif"]);
+const FILE_TYPES = { "application/pdf": "pdf", "text/plain": "txt", "text/markdown": "md", "text/csv": "csv" };
+const FILE_EXTS = new Set(["pdf", "txt", "md", "csv"]);
+
+function upload(res, form) {
+  const file = form?.files.file;
+  const conversationId = form?.fields.conversation_id;
+  if (!file || !conversationId) return json(res, 400, { error: "file and conversation_id are required" });
+  if (!conversations.has(conversationId)) return json(res, 404, { error: "conversation not found" });
+  if (file.data.length > 10 * 1024 * 1024) return json(res, 413, { error: "File too large" });
+  const type = file.type.split(";")[0].trim().toLowerCase();
+  if (IMAGE_TYPES.has(type)) {
+    const key = `conversations/${conversationId}/${uuid()}.${type.split("/")[1].replace("jpeg", "jpg")}`;
+    blobs.set(key, { bytes: file.data, type, name: file.filename });
+    return json(res, 200, { kind: "image", image_key: key });
+  }
+  const fromName = path.extname(file.filename).slice(1).toLowerCase();
+  const ext = FILE_TYPES[type] ?? (FILE_EXTS.has(fromName) ? fromName : null);
+  if (!ext) {
+    return json(res, 415, { error: `Unsupported file type: ${type || file.filename}. Allowed: images, PDF, TXT, MD, CSV` });
+  }
+  if (ext === "pdf" && /scan/i.test(file.filename)) {
+    return json(res, 422, { error: "This PDF has no text layer (scanned?), so Simba can't read it yet." });
+  }
+  const key = `conversations/${conversationId}/files/${uuid()}.${ext}`;
+  blobs.set(key, { bytes: file.data, type, name: file.filename });
+  return json(res, 200, { kind: "file", file_key: key, name: file.filename, chars: ext === "pdf" ? 1834 : file.data.length });
+}
+
+const summary = (c) => ({ id: c.id, name: c.name, created_at: c.created_at, updated_at: c.updated_at });
+
+async function api(req, res, url) {
+  const p = url.pathname.replace(/\/+$/, "") || "/";
+  const m = req.method;
+  const body = m === "GET" ? {} : await readBody(req);
+  const { form } = body;
+  requests.push({
+    method: m,
+    path: url.pathname + url.search,
+    body: form
+      ? {
+          ...form.fields,
+          files: Object.fromEntries(
+            Object.entries(form.files).map(([k, f]) => [k, { filename: f.filename, type: f.type, size: f.data.length }]),
+          ),
+        }
+      : body,
+  });
+
+  if (p === "/api/user/me") {
+    return json(res, 200, { id: "u1", username: "ryan", email: "ryan@example.com", is_admin: true });
+  }
+  if (p === "/api/user/refresh") return json(res, 200, { access_token: "mock-access-token" });
+  if (p === "/api/user/oidc/login" || p === "/api/user/login") return json(res, 200, {});
+  if (p === "/api/user/admin/users") return json(res, 200, []);
+  if (p.startsWith("/api/scheduled")) return json(res, 200, []);
+
+  if (p === "/api/conversation/stream-query" && m === "POST") {
+    return streamQuery(req, res, body);
+  }
+  if (p === "/api/conversation/query" && m === "POST") {
+    return json(res, 200, { response: "meow (mock)" });
+  }
+  if (p === "/api/conversation/upload" && m === "POST") return upload(res, form);
+  if (p === "/api/conversation/upload-image") {
+    return json(res, 200, { image_key: `mock/${uuid()}.png` });
+  }
+  if (p.startsWith("/api/conversation/image/")) {
+    const key = decodeURIComponent(p.slice("/api/conversation/image/".length));
+    return json(res, 200, { url: blobs.has(key) ? `/__mock/blob/${encodeURIComponent(key)}` : "/favicon.ico" });
+  }
+  if (p === "/api/conversation") {
+    if (m === "POST") return json(res, 200, summary(newConversation()));
+    const search = (url.searchParams.get("search") ?? "").toLowerCase();
+    let list = [...conversations.values()]
+      .filter((c) => c.name.toLowerCase().includes(search))
+      .sort((a, b) => b.updated_at.localeCompare(a.updated_at))
+      .map(summary);
+    const limit = url.searchParams.get("limit");
+    if (limit != null) {
+      const offset = Number(url.searchParams.get("offset") ?? 0);
+      list = list.slice(offset, offset + Number(limit));
+    }
+    return json(res, 200, list);
+  }
+  const conv = p.match(/^\/api\/conversation\/([^/]+)$/);
+  if (conv) {
+    const c = conversations.get(conv[1]);
+    if (!c) return json(res, 404, { error: "conversation not found" });
+    if (m === "DELETE") {
+      conversations.delete(c.id);
+      return json(res, 200, { success: true });
+    }
+    if (m === "PATCH") {
+      c.name = body.name ?? c.name;
+      return json(res, 200, summary(c));
+    }
+    return json(res, 200, {
+      ...summary(c),
+      messages: c.messages.map(({ id, text, speaker, created_at, image_key, tool, label, artifact }) =>
+        speaker === "tool"
+          ? { id, text, speaker, created_at, image_key, ...(tool ? { tool, label, artifact } : {}) }
+          : { id, text, speaker, created_at, image_key },
+      ),
+    });
+  }
+
+  if (p === "/api/artifacts") {
+    await sleep(300); // long enough to see the panel's loading states
+    const cid = url.searchParams.get("conversation_id");
+    return json(
+      res,
+      200,
+      [...artifacts.values()]
+        .filter((a) => !cid || a.conversation_id === cid)
+        .map((a) => ({ ...refOf(a), tool: a.tool, message_id: a.message_id, created_at: a.created_at })),
+    );
+  }
+  const art = p.match(/^\/api\/artifacts\/([^/]+)$/);
+  if (art) {
+    await sleep(400);
+    const a = artifacts.get(art[1]);
+    if (!a) return json(res, 404, { error: "not found" });
+    if (a.broken) return json(res, 500, { error: "Internal error" });
+    const { broken, ...artifact } = a;
+    return json(res, 200, artifact);
+  }
+
+  return json(res, 404, { error: `mock: no route for ${m} ${p}` });
+}
+
+function serveStatic(res, pathname) {
+  const file = path.join(distDir, path.normalize(pathname));
+  if (file.startsWith(distDir) && fs.existsSync(file) && fs.statSync(file).isFile()) {
+    res.writeHead(200, { "Content-Type": MIME[path.extname(file)] ?? "application/octet-stream" });
+    return fs.createReadStream(file).pipe(res);
+  }
+  // SPA catch-all, like app.py.
+  const index = path.join(distDir, "index.html");
+  if (!fs.existsSync(index)) {
+    res.writeHead(500);
+    return res.end("dist/index.html missing: run `yarn build` first");
+  }
+  res.writeHead(200, { "Content-Type": MIME[".html"] });
+  fs.createReadStream(index).pipe(res);
+}
+
+http
+  .createServer(async (req, res) => {
+    const url = new URL(req.url, `http://${req.headers.host}`);
+    try {
+      if (url.pathname === "/__mock/requests") return json(res, 200, requests);
+      if (url.pathname.startsWith("/__mock/blob/")) {
+        const blob = blobs.get(decodeURIComponent(url.pathname.slice("/__mock/blob/".length)));
+        if (!blob) return json(res, 404, { error: "no blob" });
+        res.writeHead(200, { "Content-Type": blob.type });
+        return res.end(blob.bytes);
+      }
+      if (url.pathname.startsWith("/api/")) return await api(req, res, url);
+      return serveStatic(res, decodeURIComponent(url.pathname));
+    } catch (err) {
+      console.error(err);
+      if (!res.headersSent) json(res, 500, { error: String(err) });
+    }
+  })
+  .listen(port, () => console.log(`mock SimbaRAG on http://localhost:${port}`));
diff --git a/tests/unit/test_context_trim.py b/tests/unit/test_context_trim.py
new file mode 100644
index 0000000..6764133
--- /dev/null
+++ b/tests/unit/test_context_trim.py
@@ -0,0 +1,272 @@
+"""Regression tests for complete-turn context budgeting."""
+
+import pytest
+from langchain_core.messages import AIMessage, HumanMessage, SystemMessage, ToolMessage
+
+from blueprints.conversation import context
+from blueprints.conversation.context import (
+    IMAGE_PLACEHOLDER,
+    build_context,
+    message_tokens,
+    trim_history,
+)
+
+
+def call(*ids):
+    return AIMessage(
+        content="",
+        tool_calls=[
+            {"id": i, "name": "search", "args": {"path": "notes/budget.md"}}
+            for i in ids
+        ],
+    )
+
+
+def result(i, content="found"):
+    return ToolMessage(content=content, tool_call_id=i)
+
+
+def cost(messages):
+    return sum(message_tokens(m) for m in messages)
+
+
+def test_long_current_turn_keeps_question_and_all_exchanges():
+    question = HumanMessage(content="Compare my spending with my plan")
+    messages = [question]
+    for i in range(8):
+        messages += [call(str(i)), result(str(i), "data " * 1000)]
+    out = trim_history(messages, token_budget=3000)
+    assert out[0] is question
+    assert len(out) == 17
+    assert cost(out) <= 3000
+    assert [m.tool_call_id for m in out if isinstance(m, ToolMessage)] == [
+        str(i) for i in range(8)
+    ]
+    assert messages[2].content == "data " * 1000
+    assert out[1].tool_calls == messages[1].tool_calls
+
+
+def test_parallel_tool_results_remain_paired():
+    messages = [
+        HumanMessage(content="q"),
+        call("a", "b"),
+        result("a", "x" * 20000),
+        result("b", "y" * 20000),
+    ]
+    out = trim_history(messages, token_budget=700)
+    assert len(out) == 4
+    assert out[1].tool_calls == messages[1].tool_calls
+    assert cost(out) <= 700
+
+
+def test_drops_whole_turns_and_includes_bounded_excerpts():
+    messages = []
+    for i in range(12):
+        messages += [
+            HumanMessage(content=f"Question {i}"),
+            call(str(i)),
+            result(str(i), "data " * 1000),
+            AIMessage(content=f"Decision {i}"),
+        ]
+    question = HumanMessage(content="What did we decide?")
+    messages.append(question)
+    out = trim_history(messages, token_budget=3000)
+    assert isinstance(out[0], SystemMessage)
+    assert "Decision" in out[0].content
+    assert "historical data" in out[0].content
+    assert cost(out) <= 3000
+    assert out[-1] is question
+    # Every retained result still has its original call preceding it.
+    seen = set()
+    for m in out:
+        if isinstance(m, AIMessage):
+            seen.update(c["id"] for c in m.tool_calls)
+        if isinstance(m, ToolMessage):
+            assert m.tool_call_id in seen
+
+
+def test_earlier_images_replaced_current_image_preserved():
+    image = {"type": "image_url", "image_url": {"url": "data:image/png;base64,AAAA"}}
+    messages = [
+        HumanMessage(content=[{"type": "text", "text": "old"}, image]),
+        AIMessage(content="photo"),
+        HumanMessage(content=[{"type": "text", "text": "new"}, image]),
+    ]
+    out = trim_history(messages)
+    assert out[0].content[1] == {"type": "text", "text": IMAGE_PLACEHOLDER}
+    assert out[-1].content[1] == image
+    assert messages[0].content[1] == image
+
+
+def test_short_history_unchanged():
+    messages = [HumanMessage(content="hi"), AIMessage(content="hello")]
+    assert trim_history(messages) == messages
+
+
+def test_question_that_cannot_fit_fails_without_truncation():
+    messages = [HumanMessage(content="important request " * 1000)]
+    with pytest.raises(ValueError, match="current question"):
+        trim_history(messages, token_budget=100)
+    assert messages[0].content == "important request " * 1000
+
+
+def test_system_and_tool_schemas_are_charged_to_budget(monkeypatch):
+    monkeypatch.setattr(context, "PROMPT_BUDGET_TOKENS", 2500)
+    monkeypatch.setattr(context, "CONTEXT_WINDOW_TOKENS", 10000)
+    schemas = [{"name": "search", "description": "tool docs " * 100}]
+    messages = [HumanMessage(content="q"), call("a"), result("a", "result " * 3000)]
+    out = build_context(messages, "system " * 100, schemas)
+    assert cost(out) + context.estimate_tokens(schemas) <= 2500
+    assert out[1] is messages[0]
+
+
+def test_fixed_overhead_that_cannot_fit_fails(monkeypatch):
+    monkeypatch.setattr(context, "PROMPT_BUDGET_TOKENS", 100)
+    with pytest.raises(ValueError, match="tool definitions"):
+        build_context([HumanMessage(content="q")], "system" * 1000, [])
+
+
+def test_response_and_safety_reserves_reduce_prompt_limit(monkeypatch):
+    monkeypatch.setattr(context, "CONTEXT_WINDOW_TOKENS", 8000)
+    monkeypatch.setattr(context, "PROMPT_BUDGET_TOKENS", 16000)
+    messages = [HumanMessage(content="q"), call("a"), result("a", "data " * 5000)]
+    out = build_context(messages, "system", [])
+    assert (
+        cost(out) + context.estimate_tokens([])
+        <= 8000 - context.RESPONSE_RESERVE_TOKENS - context.SAFETY_RESERVE_TOKENS
+    )
+
+
+def test_cancelled_turn_does_not_replay_incomplete_exchange():
+    messages = [
+        HumanMessage(content="old"),
+        call("a", "b"),
+        result("a"),
+        HumanMessage(content="new"),
+    ]
+    out = trim_history(messages)
+    assert out == [messages[0], messages[-1]]
+
+
+def test_orphan_results_are_removed():
+    messages = [
+        result("orphan"),
+        HumanMessage(content="q"),
+        result("another orphan"),
+        AIMessage(content="answer"),
+    ]
+    assert trim_history(messages) == [messages[1], messages[3]]
+
+
+def test_large_assistant_answer_is_bounded_in_earlier_turn():
+    messages = [
+        HumanMessage(content="old"),
+        AIMessage(content="long " * 10000),
+        HumanMessage(content="new"),
+    ]
+    out = trim_history(messages, token_budget=4000)
+    assert cost(out) <= 4000
+    assert len(out[1].content) < len(messages[1].content)
+    assert messages[1].content == "long " * 10000
+
+
+def test_multiblock_attachment_shares_one_cap():
+    messages = [
+        HumanMessage(content=[{"type": "text", "text": "x" * 10000} for _ in range(5)]),
+        AIMessage(content="ok"),
+        HumanMessage(content="next"),
+    ]
+    out = trim_history(messages, token_budget=5000)
+    assert cost(out) <= 5000
+    assert sum(len(p["text"]) for p in out[0].content) < 5000
+
+
+async def test_saved_memories_are_bounded_without_deleting(monkeypatch):
+    from blueprints.conversation import memory
+
+    saved = ["newest preference", "big " * 5000, "older preference"]
+
+    async def get_memories(user_id):
+        return saved
+
+    monkeypatch.setattr(memory, "get_memories_for_user", get_memories)
+    prompt = await memory.build_system_prompt_with_memories("user")
+    block = prompt.split("USER MEMORIES", 1)[1]
+    assert "newest preference" in block
+    assert "older preference" in block
+    assert "omitted" in block
+    assert "big big" not in block
+    assert saved[1] == "big " * 5000
+
+
+def test_agent_prompt_accounts_for_extra_tool_schemas(monkeypatch):
+    monkeypatch.setenv("TAVILY_API_KEY", "test-key")
+    from blueprints.conversation import agents
+
+    captured = {}
+
+    def create(**kwargs):
+        captured.update(kwargs)
+
+    monkeypatch.setattr(agents, "create_react_agent", create)
+    extra = {
+        "type": "function",
+        "function": {
+            "name": "extra",
+            "description": "extra docs",
+            "parameters": {"type": "object", "properties": {}},
+        },
+    }
+    agents.build_agent(extra_tools=[extra])
+    assert extra in captured["tools"]
+    question = HumanMessage(content="hello")
+    actual = captured["prompt"].invoke({"messages": [question]})
+    assert actual[-1] is question
+    # The actual prompt closure includes this schema rather than relying on a
+    # static reserve that would miss admin-only tools.
+    seen = {}
+
+    def build(messages, system, schemas):
+        seen["schemas"] = schemas
+        return messages
+
+    monkeypatch.setattr(agents, "build_context", build)
+    messages = [HumanMessage(content="hello")]
+    assert captured["prompt"].invoke({"messages": messages}) == messages
+    assert extra in seen["schemas"]
+
+
+def test_heavy_current_turn_leaves_room_for_previous_decisions():
+    question = HumanMessage(content="Apply that plan to my spending")
+    messages = [
+        HumanMessage(content="Plan?"),
+        AIMessage(content="Keep dining under $300."),
+        question,
+        call("a"),
+        result("a", "spending " * 10000),
+    ]
+    out = trim_history(messages, token_budget=2500)
+    assert cost(out) <= 2500
+    assert question in out
+    assert any(
+        "Keep dining under $300." in m.content
+        for m in out
+        if isinstance(m.content, str)
+    )
+
+
+def test_large_tool_arguments_fail_explicitly_instead_of_breaking_pair():
+    exchange = call("a")
+    exchange.tool_calls[0]["args"] = {"query": "huge " * 10000}
+    messages = [HumanMessage(content="q"), exchange, result("a")]
+    with pytest.raises(ValueError, match="tool calls exceed"):
+        trim_history(messages, token_budget=300)
+    assert exchange.tool_calls[0]["args"]["query"] == "huge " * 10000
+
+
+def test_unicode_tool_result_fits_estimated_budget():
+    messages = [HumanMessage(content="q"), call("a"), result("a", "猫😺预算" * 10000)]
+    out = trim_history(messages, token_budget=600)
+    assert cost(out) <= 600
+    assert out[0] is messages[0]
+    assert out[1].tool_calls == messages[1].tool_calls
diff --git a/tests/unit/test_file_upload.py b/tests/unit/test_file_upload.py
new file mode 100644
index 0000000..6af945c
--- /dev/null
+++ b/tests/unit/test_file_upload.py
@@ -0,0 +1,282 @@
+"""Tests for conversation file attachments: extraction, /upload and stream-query file_key."""
+
+import io
+from datetime import timedelta
+from types import SimpleNamespace
+from unittest.mock import AsyncMock, patch
+
+import fitz
+import pytest
+from PIL import Image
+from quart import Quart
+from quart.datastructures import FileStorage
+from quart_jwt_extended import JWTManager, create_access_token
+
+import blueprints.conversation as conv
+from utils.file_extract import (
+    MAX_ATTACHMENT_CHARS,
+    TRUNCATION_MARKER,
+    FileExtractionError,
+    attachment_block,
+    cap_text,
+    extract_text,
+    file_extension,
+)
+
+CONV_ID = "11111111-1111-1111-1111-111111111111"
+OTHER_ID = "22222222-2222-2222-2222-222222222222"
+
+
+def _pdf_bytes(text: str) -> bytes:
+    doc = fitz.open()
+    page = doc.new_page()
+    page.insert_text((72, 72), text)
+    data = doc.tobytes()
+    doc.close()
+    return data
+
+
+def _png_bytes() -> bytes:
+    buf = io.BytesIO()
+    Image.new("RGB", (4, 4), "orange").save(buf, format="PNG")
+    return buf.getvalue()
+
+
+class TestFileExtension:
+    @pytest.mark.parametrize(
+        "name,mime,expected",
+        [
+            ("a.pdf", "application/pdf", "pdf"),
+            ("notes", "text/markdown", "md"),
+            ("notes.md", "application/octet-stream", "md"),
+            ("data.CSV", "", "csv"),
+            ("x.txt", "text/plain; charset=utf-8", "txt"),
+            ("x.markdown", None, "md"),
+            ("x.docx", "application/vnd.openxmlformats", None),
+            ("x.zip", "application/zip", None),
+        ],
+    )
+    def test_detects_supported_types(self, name, mime, expected):
+        assert file_extension(name, mime) == expected
+
+
+class TestExtractText:
+    def test_pdf(self):
+        assert "Simba eats kibble" in extract_text(
+            _pdf_bytes("Simba eats kibble"), "pdf"
+        )
+
+    def test_corrupt_pdf_raises(self):
+        with pytest.raises(FileExtractionError):
+            extract_text(b"not a pdf", "pdf")
+
+    def test_text_decodes_utf8_with_replacement(self):
+        assert extract_text("héllo".encode() + b"\xff", "txt") == "héllo�"
+
+    def test_csv_and_md_are_plain_text(self):
+        assert extract_text(b"\xef\xbb\xbfa,b\n1,2", "csv") == "a,b\n1,2"
+        assert extract_text(b"# Title", "md") == "# Title"
+
+
+class TestTruncation:
+    def test_short_text_untouched(self):
+        assert cap_text("abc") == "abc"
+
+    def test_long_text_capped_with_marker(self):
+        out = cap_text("x" * (MAX_ATTACHMENT_CHARS + 50))
+        assert out.endswith(TRUNCATION_MARKER)
+        assert out.count("x") == MAX_ATTACHMENT_CHARS
+
+    def test_attachment_block_wraps_and_caps(self):
+        block = attachment_block('a"b.txt', "y" * (MAX_ATTACHMENT_CHARS + 1))
+        assert block.startswith('<attached file "a\'b.txt">\n')
+        assert block.endswith(f"{TRUNCATION_MARKER}\n</attached>")
+
+
+class TestFileKeyPrefix:
+    def test_own_conversation(self):
+        assert conv._file_key_belongs_to(
+            f"conversations/{CONV_ID}/files/x.pdf", CONV_ID
+        )
+
+    @pytest.mark.parametrize(
+        "key",
+        [
+            f"conversations/{OTHER_ID}/files/x.pdf",
+            f"conversations/{CONV_ID}/x.jpg",
+            f"conversations/{CONV_ID}/files/../../{OTHER_ID}/files/x.pdf",
+            f"conversations/{CONV_ID}",
+            None,
+        ],
+    )
+    def test_rejects_other_keys(self, key):
+        assert not conv._file_key_belongs_to(key, CONV_ID)
+
+
+@pytest.fixture
+def app():
+    app = Quart(__name__)
+    app.config["JWT_SECRET_KEY"] = "test-secret"
+    app.config["JWT_ACCESS_TOKEN_EXPIRES"] = timedelta(hours=1)
+    JWTManager(app)
+    app.register_blueprint(conv.conversation_blueprint)
+    return app
+
+
+@pytest.fixture
+async def headers(app):
+    async with app.app_context():
+        token = create_access_token(identity="user-1")
+    return {"Authorization": f"Bearer {token}"}
+
+
+def _owned(conversation_id, user_id):
+    if conversation_id == CONV_ID and user_id == "user-1":
+        return SimpleNamespace(id=CONV_ID)
+    return None
+
+
+@pytest.fixture
+def s3():
+    with (
+        patch.object(conv, "_get_owned_conversation", AsyncMock(side_effect=_owned)),
+        patch.object(conv, "s3_upload_file", AsyncMock()) as upload_file,
+        patch.object(conv, "s3_upload_image", AsyncMock()) as upload_image,
+    ):
+        yield SimpleNamespace(upload_file=upload_file, upload_image=upload_image)
+
+
+async def _upload(
+    app, headers, data: bytes, filename: str, mime: str, conversation_id=CONV_ID
+):
+    return await app.test_client().post(
+        "/api/conversation/upload",
+        headers=headers,
+        form={"conversation_id": conversation_id},
+        files={
+            "file": FileStorage(io.BytesIO(data), filename=filename, content_type=mime)
+        },
+    )
+
+
+class TestUploadRoute:
+    async def test_pdf_is_stored_with_filename(self, app, headers, s3):
+        resp = await _upload(
+            app, headers, _pdf_bytes("hello"), "Vet bill.pdf", "application/pdf"
+        )
+        assert resp.status_code == 200
+        body = await resp.get_json()
+        assert body["kind"] == "file"
+        assert body["name"] == "Vet bill.pdf"
+        assert body["chars"] >= len("hello")
+        assert body["file_key"].startswith(f"conversations/{CONV_ID}/files/")
+        assert body["file_key"].endswith(".pdf")
+        _, key, mime, metadata = s3.upload_file.await_args.args
+        assert key == body["file_key"] and mime == "application/pdf"
+        assert metadata == {"filename": "Vet%20bill.pdf"}
+
+    async def test_markdown_by_extension(self, app, headers, s3):
+        resp = await _upload(app, headers, b"# hi", "n.md", "application/octet-stream")
+        body = await resp.get_json()
+        assert resp.status_code == 200
+        assert body["chars"] == 4 and body["file_key"].endswith(".md")
+
+    async def test_image_goes_through_process_image(self, app, headers, s3):
+        resp = await _upload(app, headers, _png_bytes(), "cat.png", "image/png")
+        assert resp.status_code == 200
+        body = await resp.get_json()
+        assert body["kind"] == "image"
+        assert body["image_key"].startswith(f"conversations/{CONV_ID}/")
+        s3.upload_image.assert_awaited_once()
+        s3.upload_file.assert_not_awaited()
+
+    async def test_unsupported_type_is_415(self, app, headers, s3):
+        resp = await _upload(app, headers, b"PK\x03\x04", "a.zip", "application/zip")
+        assert resp.status_code == 415
+        s3.upload_file.assert_not_awaited()
+
+    async def test_unsupported_image_type_is_415(self, app, headers, s3):
+        resp = await _upload(app, headers, b"GIF89a", "a.gif", "image/gif")
+        assert resp.status_code == 415
+
+    async def test_corrupt_pdf_is_400(self, app, headers, s3):
+        resp = await _upload(app, headers, b"nope", "a.pdf", "application/pdf")
+        assert resp.status_code == 400
+
+    async def test_pdf_without_text_layer_is_422(self, app, headers, s3):
+        doc = fitz.open()
+        doc.new_page()  # blank page: no text, like a scan without OCR
+        resp = await _upload(app, headers, doc.tobytes(), "scan.pdf", "application/pdf")
+        assert resp.status_code == 422
+        assert "no text layer" in (await resp.get_json())["error"]
+        s3.upload_file.assert_not_awaited()
+
+    async def test_empty_text_file_is_422(self, app, headers, s3):
+        resp = await _upload(app, headers, b"  \n", "empty.txt", "text/plain")
+        assert resp.status_code == 422
+        s3.upload_file.assert_not_awaited()
+
+    async def test_extraction_runs_off_the_event_loop(self, app, headers, s3):
+        calls = []
+
+        async def fake_to_thread(fn, *args):
+            calls.append(fn)
+            return fn(*args)
+
+        with patch.object(conv.asyncio, "to_thread", fake_to_thread):
+            resp = await _upload(
+                app, headers, _pdf_bytes("hi"), "a.pdf", "application/pdf"
+            )
+            get = AsyncMock(return_value=(b"x", {}))
+            with patch.object(conv, "s3_get_file", get):
+                await conv._load_attached_file(f"conversations/{CONV_ID}/files/u.txt")
+        assert resp.status_code == 200
+        assert calls == [conv.extract_text, conv.extract_text]
+
+    async def test_other_users_conversation_is_404(self, app, headers, s3):
+        resp = await _upload(
+            app, headers, b"hi", "a.txt", "text/plain", conversation_id=OTHER_ID
+        )
+        assert resp.status_code == 404
+        s3.upload_file.assert_not_awaited()
+
+    async def test_requires_auth(self, app, s3):
+        resp = await _upload(app, {}, b"hi", "a.txt", "text/plain")
+        assert resp.status_code == 401
+
+
+class TestStreamQueryFileKey:
+    async def test_rejects_file_key_from_other_conversation(self, app, headers, s3):
+        add = AsyncMock()
+        with (
+            patch.object(conv.blueprints.users.models.User, "get", AsyncMock()),
+            patch.object(conv, "add_message_to_conversation", add),
+        ):
+            resp = await app.test_client().post(
+                "/api/conversation/stream-query",
+                headers=headers,
+                json={
+                    "query": "summarise",
+                    "conversation_id": CONV_ID,
+                    "file_key": f"conversations/{OTHER_ID}/files/x.pdf",
+                },
+            )
+        assert resp.status_code == 400
+        add.assert_not_awaited()
+
+    async def test_load_attached_file_recovers_name_and_text(self):
+        get = AsyncMock(return_value=(b"a,b\n1,2", {"filename": "M%C3%A9nage.csv"}))
+        with patch.object(conv, "s3_get_file", get):
+            name, text = await conv._load_attached_file(
+                f"conversations/{CONV_ID}/files/u.csv"
+            )
+        assert name == "Ménage.csv"
+        assert text == "a,b\n1,2"
+
+    async def test_load_attached_file_falls_back_to_key_name(self):
+        get = AsyncMock(return_value=(b"x", {}))
+        with patch.object(conv, "s3_get_file", get):
+            name, _ = await conv._load_attached_file(
+                f"conversations/{CONV_ID}/files/u.txt"
+            )
+        assert name == "u.txt"
diff --git a/tests/unit/test_stream_stall.py b/tests/unit/test_stream_stall.py
new file mode 100644
index 0000000..51e14da
--- /dev/null
+++ b/tests/unit/test_stream_stall.py
@@ -0,0 +1,220 @@
+"""Tests for the stream-query stall timeout and per-call model metrics."""
+
+import asyncio
+import json
+import logging
+
+import pytest
+from langchain_core.messages import AIMessage, AIMessageChunk
+from quart import Quart
+from quart_jwt_extended import JWTManager, create_access_token
+from tortoise import Tortoise
+
+import blueprints.conversation as conv
+from blueprints.conversation.models import Conversation
+from blueprints.users.models import User
+
+# Shortened stall limit for the tests (seconds).
+LIMIT = 0.3
+
+
+@pytest.fixture
+async def owner():
+    await Tortoise.init(
+        db_url="sqlite://:memory:",
+        modules={
+            "models": [
+                "blueprints.users.models",
+                "blueprints.conversation.models",
+                "blueprints.artifacts.models",
+            ]
+        },
+    )
+    await Tortoise.generate_schemas()
+    user = await User.create(username="owner", email="owner@example.com")
+    conversation = await Conversation.create(name="c", user=user)
+    yield user, conversation
+    await Tortoise.close_connections()
+
+
+class _TimedAgent:
+    """Yields (delay_seconds, event) pairs, sleeping before each event."""
+
+    def __init__(self, script):
+        self._script = script
+
+    async def astream_events(self, payload, version, config):
+        for delay, event in self._script:
+            await asyncio.sleep(delay)
+            yield event
+
+
+def _start(run_id):
+    return {"event": "on_chat_model_start", "run_id": run_id, "name": "llm", "data": {}}
+
+
+def _chunk(run_id, text):
+    return {
+        "event": "on_chat_model_stream",
+        "run_id": run_id,
+        "data": {"chunk": AIMessageChunk(content=text)},
+    }
+
+
+def _end(run_id, prompt_tokens=None):
+    usage = (
+        {
+            "input_tokens": prompt_tokens,
+            "output_tokens": 5,
+            "total_tokens": prompt_tokens + 5,
+        }
+        if prompt_tokens
+        else None
+    )
+    return {
+        "event": "on_chat_model_end",
+        "run_id": run_id,
+        "data": {"output": AIMessage(content="", usage_metadata=usage)},
+    }
+
+
+def _final(text):
+    return {
+        "event": "on_chain_end",
+        "name": "agent",
+        "data": {"output": {"messages": [AIMessage(content=text)]}},
+    }
+
+
+async def _run(owner, monkeypatch, script, *, response_timeout=60):
+    user, conversation = owner
+    monkeypatch.setattr(conv, "MODEL_STALL_TIMEOUT", LIMIT)
+    monkeypatch.setattr(conv, "get_agent_for", lambda u: _TimedAgent(script))
+
+    async def _prompt(user_id):
+        return "system"
+
+    monkeypatch.setattr(conv, "build_system_prompt_with_memories", _prompt)
+
+    app = Quart(__name__)
+    app.config["RESPONSE_TIMEOUT"] = response_timeout
+    app.config["JWT_SECRET_KEY"] = "test-secret"
+    JWTManager(app)
+    app.register_blueprint(conv.conversation_blueprint)
+    async with app.app_context():
+        token = create_access_token(identity=str(user.id))
+    resp = await app.test_client().post(
+        "/api/conversation/stream-query",
+        json={"query": "hi", "conversation_id": str(conversation.id)},
+        headers={"Authorization": f"Bearer {token}"},
+    )
+    body = (await resp.get_data()).decode()
+    return [
+        json.loads(line[len("data: ") :])
+        for line in body.splitlines()
+        if line.startswith("data: {")
+    ]
+
+
+def test_stall_timeout_only_while_a_model_call_is_in_flight(monkeypatch):
+    monkeypatch.setattr(conv, "MODEL_STALL_TIMEOUT", 30.0)
+    assert conv.stall_timeout(None, 100.0) is None
+    assert conv.stall_timeout(100.0, 110.0) == 20.0
+    assert conv.stall_timeout(100.0, 200.0) == 1.0  # floor
+
+
+async def test_active_stream_outlasts_response_timeout(owner, monkeypatch):
+    script = [
+        (0, _start("m1")),
+        (0, _chunk("m1", "<think>")),
+        (0.15, _chunk("m1", "working")),
+        (0.15, _chunk("m1", "</think>Answer")),
+        (0, _end("m1")),
+        (0, _final("Answer")),
+    ]
+
+    frames = await _run(owner, monkeypatch, script, response_timeout=0.1)
+
+    assert "error" not in [f["type"] for f in frames]
+    assert frames[-1] == {"type": "response", "message": "Answer"}
+
+
+async def test_long_thinking_is_not_a_stall(owner, monkeypatch):
+    # The whole call takes ~4x the limit, but output never pauses for longer
+    # than half of it; the old time-to-first-content deadline killed this.
+    script = [(0, _start("m1"))]
+    script += [(LIMIT / 2, _chunk("m1", "<think>hmm ")) for _ in range(8)]
+    script += [
+        (0, _chunk("m1", "</think>Answer")),
+        (0, _end("m1")),
+        (0, _final("Answer")),
+    ]
+
+    frames = await _run(owner, monkeypatch, script)
+
+    types = [f["type"] for f in frames]
+    assert "error" not in types
+    assert frames[-1] == {"type": "response", "message": "Answer"}
+
+
+async def test_tool_time_between_model_calls_does_not_count(owner, monkeypatch):
+    tool = {"event": "on_tool_start", "name": "web_search", "run_id": "t1", "data": {}}
+    tool_end = {
+        "event": "on_tool_end",
+        "name": "web_search",
+        "run_id": "t1",
+        "data": {},
+    }
+    script = [
+        (0, _start("m1")),
+        (0, _chunk("m1", "")),
+        (0, _end("m1")),
+        (0, tool),
+        (LIMIT * 3, tool_end),  # slow tool, no model call in flight
+        (0, _start("m2")),
+        (LIMIT / 2, _chunk("m2", "Done")),
+        (0, _end("m2")),
+        (0, _final("Done")),
+    ]
+
+    frames = await _run(owner, monkeypatch, script)
+
+    assert "error" not in [f["type"] for f in frames]
+    assert frames[-1]["message"] == "Done"
+
+
+async def test_silent_model_call_is_a_stall(owner, monkeypatch):
+    script = [
+        (0, _start("m1")),
+        (0, _chunk("m1", "<think>start")),
+        (LIMIT * 4, _chunk("m1", "never arrives")),
+    ]
+
+    frames = await _run(owner, monkeypatch, script)
+
+    assert frames[-1]["type"] == "error"
+    assert frames[-1]["stalled"] is True
+
+
+async def test_logs_per_call_prompt_tokens(owner, monkeypatch, caplog):
+    script = [
+        (0, _start("m1")),
+        (0, _chunk("m1", "Hi")),
+        (0, _end("m1", prompt_tokens=27262)),
+        (0, _final("Hi")),
+    ]
+
+    with caplog.at_level(logging.INFO):
+        await _run(owner, monkeypatch, script)
+
+    summaries = [
+        json.loads(r.getMessage())
+        for r in caplog.records
+        if r.getMessage().startswith('{"event": "stream_request"')
+    ]
+    assert summaries, "stream_request summary not logged"
+    summary = summaries[-1]
+    assert summary["max_prompt_tokens"] == 27262
+    (call,) = summary["model_calls"]
+    assert call["prompt_tokens"] == 27262
+    assert call["prefill_ms"] is not None and call["ms"] is not None
diff --git a/tests/unit/test_tool_artifacts.py b/tests/unit/test_tool_artifacts.py
new file mode 100644
index 0000000..a16196f
--- /dev/null
+++ b/tests/unit/test_tool_artifacts.py
@@ -0,0 +1,614 @@
+"""Tests for tools returning (text, artifact) via content_and_artifact.
+
+The text half must stay identical to the pre-artifact output (the LLM's view),
+and the artifact must match the contract in docs/cowork-ui-plan.md.
+"""
+
+import datetime
+import json
+import os
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+from langchain_core.documents import Document
+from langchain_core.messages import ToolMessage
+
+os.environ.setdefault("TAVILY_API_KEY", "dummy")
+
+from blueprints.conversation import agents  # noqa: E402
+from blueprints.conversation.artifacts_util import (  # noqa: E402
+    NOTE_MAX_CHARS,
+    SNIPPET_MAX_CHARS,
+    format_date_range,
+    search_documents_artifact,
+)
+from utils.obsidian_service import ObsidianService  # noqa: E402
+
+KIND_DATA_KEYS = {
+    "mealie.recipe": {
+        "slug",
+        "name",
+        "description",
+        "servings",
+        "prep_time",
+        "cook_time",
+        "total_time",
+        "ingredients",
+        "instructions",
+        "tags",
+    },
+    "mealie.meal_plan": {"start_date", "end_date", "days"},
+    "mealie.shopping_lists": {"lists"},
+    "obsidian.note": {"path", "title", "markdown", "tags", "frontmatter"},
+    "search.documents": {"query", "source", "results"},
+}
+
+
+async def call(tool, args=None) -> ToolMessage:
+    """Invoke a tool the way the agent does: with a ToolCall dict."""
+    msg = await tool.ainvoke(
+        {"type": "tool_call", "id": "call-1", "name": tool.name, "args": args or {}}
+    )
+    assert isinstance(msg, ToolMessage)
+    return msg
+
+
+def assert_artifact(artifact, kind):
+    assert artifact is not None
+    assert artifact["kind"] == kind
+    assert isinstance(artifact["title"], str) and artifact["title"]
+    assert set(artifact["data"]) == KIND_DATA_KEYS[kind]
+    json.dumps(artifact)
+
+
+@pytest.fixture
+def mealie(monkeypatch):
+    service = MagicMock()
+    monkeypatch.setattr(agents, "mealie_enabled", True)
+    monkeypatch.setattr(agents, "mealie_service", service, raising=False)
+    monkeypatch.setenv("MEALIE_BASE_URL", "http://mealie.local:9000/")
+    monkeypatch.delenv("MEALIE_GROUP_SLUG", raising=False)
+    return service
+
+
+@pytest.fixture
+def obsidian(monkeypatch, tmp_path):
+    (tmp_path / "seed.md").write_text("# seed")
+    monkeypatch.setenv("OBSIDIAN_VAULT_PATH", str(tmp_path))
+    monkeypatch.delenv("OBSIDIAN_VAULT_NAME", raising=False)
+    service = ObsidianService()
+    monkeypatch.setattr(agents, "obsidian_enabled", True)
+    monkeypatch.setattr(agents, "obsidian_service", service, raising=False)
+    return service
+
+
+# --- Mealie -----------------------------------------------------------------
+
+RECIPE = {
+    "name": "Chicken Tikka Masala",
+    "slug": "chicken-tikka-masala",
+    "description": "Creamy and spiced.",
+    "ingredients": [{"display": "1 lb chicken"}, {"display": "1 cup yogurt"}],
+    "instructions": [
+        {"title": "Marinate", "text": "Mix chicken and yogurt."},
+        {"title": "", "text": "Cook it."},
+    ],
+    "prep_time": "20 minutes",
+    "cook_time": "30 minutes",
+    "total_time": "",
+    "servings": "4",
+    "tags": ["Indian", "Dinner"],
+}
+
+RECIPE_TEXT = """**Chicken Tikka Masala**
+Creamy and spiced.
+
+Servings: 4
+Prep: 20 minutes | Cook: 30 minutes
+
+Ingredients:
+- 1 lb chicken
+- 1 cup yogurt
+
+Instructions:
+1. Mix chicken and yogurt.
+2. Cook it.
+
+Tags: Indian, Dinner"""
+
+
+async def test_mealie_get_recipe(mealie):
+    mealie.get_recipe = AsyncMock(return_value=RECIPE)
+
+    msg = await call(agents.mealie_get_recipe, {"recipe_slug": "chicken-tikka-masala"})
+
+    assert msg.content == RECIPE_TEXT
+    art = msg.artifact
+    assert_artifact(art, "mealie.recipe")
+    assert art["title"] == "Chicken Tikka Masala"
+    assert art["data"]["ingredients"] == ["1 lb chicken", "1 cup yogurt"]
+    assert art["data"]["instructions"] == [
+        {"title": "Marinate", "text": "Mix chicken and yogurt."},
+        {"text": "Cook it."},
+    ]
+    assert art["source_ref"] == {
+        "system": "mealie",
+        "id": "chicken-tikka-masala",
+        "url": "http://mealie.local:9000/g/home/r/chicken-tikka-masala",
+    }
+
+
+async def test_mealie_recipe_url_uses_group_slug(mealie, monkeypatch):
+    monkeypatch.setenv("MEALIE_GROUP_SLUG", "family")
+    mealie.get_recipe = AsyncMock(return_value=RECIPE)
+
+    msg = await call(agents.mealie_get_recipe, {"recipe_slug": "chicken-tikka-masala"})
+
+    assert msg.artifact["source_ref"]["url"].endswith(
+        "/g/family/r/chicken-tikka-masala"
+    )
+
+
+async def test_mealie_get_recipe_error(mealie):
+    mealie.get_recipe = AsyncMock(side_effect=Exception("404"))
+
+    msg = await call(agents.mealie_get_recipe, {"recipe_slug": "nope"})
+
+    assert msg.content == "Error fetching recipe: 404"
+    assert msg.artifact is None
+
+
+MEAL_PLANS = {
+    "start_date": "2026-10-12",
+    "end_date": "2026-10-19",
+    "total_plans": 3,
+    "plans_by_date": {
+        "2026-10-13": [
+            {
+                "entry_type": "dinner",
+                "title": "",
+                "recipe_name": "Tacos",
+                "recipe_slug": "tacos",
+                "note": "",
+            }
+        ],
+        "2026-10-12": [
+            {
+                "entry_type": "lunch",
+                "title": "Leftovers",
+                "recipe_name": "",
+                "recipe_slug": "",
+                "note": "from Sunday",
+            },
+            {
+                "entry_type": "dinner",
+                "title": "",
+                "recipe_name": "Chicken Tikka Masala",
+                "recipe_slug": "chicken-tikka-masala",
+                "note": "",
+            },
+        ],
+    },
+}
+
+MEAL_PLANS_TEXT = """Meal plans from 2026-10-12 to 2026-10-19 (3 meals):
+
+2026-10-12:
+  - Lunch: Leftovers
+    Note: from Sunday
+  - Dinner: Chicken Tikka Masala
+
+2026-10-13:
+  - Dinner: Tacos"""
+
+
+async def test_mealie_meal_plans(mealie):
+    mealie.get_meal_plans = AsyncMock(return_value=MEAL_PLANS)
+
+    msg = await call(agents.mealie_meal_plans, {})
+
+    assert msg.content == MEAL_PLANS_TEXT
+    art = msg.artifact
+    assert_artifact(art, "mealie.meal_plan")
+    assert art["title"] == "Meal plan · Oct 12–19"
+    assert [d["date"] for d in art["data"]["days"]] == ["2026-10-12", "2026-10-13"]
+    assert art["data"]["days"][0]["meals"] == [
+        {"entry_type": "lunch", "name": "Leftovers", "note": "from Sunday"},
+        {
+            "entry_type": "dinner",
+            "name": "Chicken Tikka Masala",
+            "recipe_slug": "chicken-tikka-masala",
+        },
+    ]
+
+
+async def test_mealie_meal_plans_empty(mealie):
+    mealie.get_meal_plans = AsyncMock(
+        return_value={
+            "start_date": "2026-10-12",
+            "end_date": "2026-10-19",
+            "total_plans": 0,
+            "plans_by_date": {},
+        }
+    )
+
+    msg = await call(agents.mealie_meal_plans, {})
+
+    assert msg.content == "No meal plans found from 2026-10-12 to 2026-10-19."
+    assert msg.artifact is None
+
+
+async def test_mealie_todays_meals(mealie):
+    mealie.get_todays_meals = AsyncMock(
+        return_value={
+            "today": "2026-10-12",
+            "total_meals": 1,
+            "meals": [
+                {
+                    "entry_type": "dinner",
+                    "title": "",
+                    "recipe_name": "Tacos",
+                    "recipe_slug": "tacos",
+                    "note": "extra salsa",
+                }
+            ],
+        }
+    )
+
+    msg = await call(agents.mealie_todays_meals)
+
+    assert msg.content == (
+        "Meals planned for today (2026-10-12):\n- Dinner: Tacos\n  Note: extra salsa"
+    )
+    art = msg.artifact
+    assert_artifact(art, "mealie.meal_plan")
+    assert art["title"] == "Today's meals · Oct 12"
+    assert art["data"] == {
+        "start_date": "2026-10-12",
+        "end_date": "2026-10-12",
+        "days": [
+            {
+                "date": "2026-10-12",
+                "meals": [
+                    {
+                        "entry_type": "dinner",
+                        "name": "Tacos",
+                        "recipe_slug": "tacos",
+                        "note": "extra salsa",
+                    }
+                ],
+            }
+        ],
+    }
+
+
+async def test_mealie_todays_meals_empty(mealie):
+    mealie.get_todays_meals = AsyncMock(
+        return_value={"today": "2026-10-12", "total_meals": 0, "meals": []}
+    )
+
+    msg = await call(agents.mealie_todays_meals)
+
+    assert msg.content == "No meals planned for today (2026-10-12)."
+    assert msg.artifact is None
+
+
+async def test_mealie_shopping_lists(mealie):
+    mealie.get_shopping_lists = AsyncMock(
+        return_value={
+            "total_lists": 1,
+            "total_unchecked_items": 2,
+            "shopping_lists": [
+                {
+                    "name": "Groceries",
+                    "unchecked_items": [
+                        {"name": "Milk", "quantity": 1, "note": "", "food": None},
+                        {"name": "Eggs", "quantity": 12.0, "note": "", "food": None},
+                    ],
+                    "checked_items": [
+                        {"name": "Bread", "quantity": 1, "note": "", "food": None}
+                    ],
+                }
+            ],
+        }
+    )
+
+    msg = await call(agents.mealie_shopping_lists)
+
+    assert msg.content == (
+        "Shopping lists (2 items needed):\n"
+        "\n**Groceries** (2 items needed)\n"
+        "  - [ ] Milk\n"
+        "  - [ ] Eggs x12.0\n"
+        "  (1 items already checked off)"
+    )
+    art = msg.artifact
+    assert_artifact(art, "mealie.shopping_lists")
+    assert art["data"]["lists"] == [
+        {
+            "name": "Groceries",
+            "items": [
+                {"name": "Milk", "quantity": 1, "checked": False},
+                {"name": "Eggs", "quantity": 12.0, "checked": False},
+                {"name": "Bread", "quantity": 1, "checked": True},
+            ],
+        }
+    ]
+
+
+async def test_mealie_shopping_lists_empty(mealie):
+    mealie.get_shopping_lists = AsyncMock(
+        return_value={
+            "total_lists": 0,
+            "total_unchecked_items": 0,
+            "shopping_lists": [],
+        }
+    )
+
+    msg = await call(agents.mealie_shopping_lists)
+
+    assert msg.content == "No shopping lists found."
+    assert msg.artifact is None
+
+
+@pytest.mark.parametrize(
+    "tool,args",
+    [
+        (agents.mealie_get_recipe, {"recipe_slug": "x"}),
+        (agents.mealie_meal_plans, {}),
+        (agents.mealie_todays_meals, {}),
+        (agents.mealie_shopping_lists, {}),
+    ],
+)
+async def test_mealie_not_configured(monkeypatch, tool, args):
+    monkeypatch.setattr(agents, "mealie_enabled", False)
+
+    msg = await call(tool, args)
+
+    assert msg.content == (
+        "Mealie integration is not configured. Please set MEALIE_BASE_URL and "
+        "MEALIE_API_TOKEN environment variables."
+    )
+    assert msg.artifact is None
+
+
+# --- Obsidian ---------------------------------------------------------------
+
+NOTE = """---
+title: Vet visit
+date: 2026-10-01
+tags: [simba]
+---
+Simba saw the [[Dr Smith|vet]] today. #simba #health #simba
+"""
+
+
+async def test_obsidian_read_note(obsidian, monkeypatch):
+    monkeypatch.setenv("OBSIDIAN_VAULT_NAME", "Home Vault")
+    os.makedirs(os.path.join(obsidian.vault_path, "notes"))
+    with open(os.path.join(obsidian.vault_path, "notes", "vet visit.md"), "w") as f:
+        f.write(NOTE)
+
+    msg = await call(agents.obsidian_read_note, {"relative_path": "notes/vet visit.md"})
+
+    assert msg.content == (
+        "File: notes/vet visit.md\n\n"
+        "Frontmatter:\n{'title': 'Vet visit', 'date': datetime.date(2026, 10, 1), "
+        "'tags': ['simba']}\n\n"
+        "Content:\nSimba saw the vet today. #simba #health #simba\n\n"
+        "Tags: simba, health, simba\n"
+        "Contains 1 wikilinks and 0 embeds"
+    )
+    art = msg.artifact
+    assert_artifact(art, "obsidian.note")
+    assert art["title"] == "Vet visit"
+    assert art["data"]["frontmatter"] == {
+        "title": "Vet visit",
+        "date": "2026-10-01",
+        "tags": ["simba"],
+    }
+    assert art["data"]["tags"] == ["simba", "health"]
+    assert art["data"]["markdown"] == "Simba saw the vet today. #simba #health #simba"
+    assert art["source_ref"] == {
+        "system": "obsidian",
+        "path": "notes/vet visit.md",
+        "url": "obsidian://open?vault=Home%20Vault&file=notes%2Fvet%20visit.md",
+    }
+
+
+async def test_obsidian_read_note_caps_markdown_and_omits_url(obsidian):
+    with open(os.path.join(obsidian.vault_path, "big.md"), "w") as f:
+        f.write("x" * (NOTE_MAX_CHARS + 500))
+
+    msg = await call(agents.obsidian_read_note, {"relative_path": "big.md"})
+
+    art = msg.artifact
+    assert art["title"] == "big"
+    assert len(art["data"]["markdown"]) <= NOTE_MAX_CHARS
+    assert art["source_ref"] == {"system": "obsidian", "path": "big.md"}
+
+
+async def test_obsidian_read_note_missing(obsidian):
+    msg = await call(agents.obsidian_read_note, {"relative_path": "nope.md"})
+
+    assert msg.content == (
+        "Note not found at 'nope.md'. Please check the path is correct."
+    )
+    assert msg.artifact is None
+
+
+async def test_journal_get_today(obsidian):
+    path = obsidian.get_daily_note_path()
+    full = os.path.join(obsidian.vault_path, path)
+    os.makedirs(os.path.dirname(full), exist_ok=True)
+    raw = "## Tasks\n- [ ] Feed Simba\n"
+    with open(full, "w") as f:
+        f.write(raw)
+    today = datetime.datetime.now().strftime("%Y-%m-%d")
+
+    msg = await call(agents.journal_get_today)
+
+    assert msg.content == f"Daily note for {today}:\n\n{raw}"
+    art = msg.artifact
+    assert_artifact(art, "obsidian.note")
+    assert art["title"].startswith("Daily note · ")
+    assert art["data"]["path"] == path
+    assert art["data"]["markdown"] == "## Tasks\n- [ ] Feed Simba"
+
+
+async def test_journal_get_today_missing(obsidian):
+    today = datetime.datetime.now().strftime("%Y-%m-%d")
+
+    msg = await call(agents.journal_get_today)
+
+    assert msg.content == (
+        f"No daily note found for {today}. Use journal_add_task to create one."
+    )
+    assert msg.artifact is None
+
+
+async def test_obsidian_not_configured(monkeypatch):
+    monkeypatch.setattr(agents, "obsidian_enabled", False)
+
+    for tool, args in [
+        (agents.obsidian_read_note, {"relative_path": "a.md"}),
+        (agents.obsidian_search_notes, {"query": "a"}),
+    ]:
+        msg = await call(tool, args)
+        assert msg.content == (
+            "Obsidian integration is not configured. Please set "
+            "OBSIDIAN_VAULT_PATH environment variable."
+        )
+        assert msg.artifact is None
+
+    msg = await call(agents.journal_get_today)
+    assert msg.content == "Obsidian integration is not configured."
+    assert msg.artifact is None
+
+
+# --- Search -----------------------------------------------------------------
+
+PAPERLESS_DOCS = [
+    Document(
+        page_content="Rabies   vaccine\nadministered. " + "y" * 600,
+        metadata={
+            "source": "paperless",
+            "created_date": 1760227200.0,
+            "filename": "vet_invoice.pdf",
+            "document_type": "Invoice",
+        },
+    )
+]
+
+
+async def test_simba_search(monkeypatch):
+    query_mock = AsyncMock(return_value=("Source: {...}\nContent: x", PAPERLESS_DOCS))
+    monkeypatch.setattr(agents, "query_vector_store", query_mock)
+
+    msg = await call(agents.simba_search, {"query": "vet records"})
+
+    assert msg.content == "Source: {...}\nContent: x"
+    query_mock.assert_awaited_once_with(query="vet records", source="paperless")
+    art = msg.artifact
+    assert_artifact(art, "search.documents")
+    assert art["title"] == "Search: vet records"
+    assert art["data"]["source"] == "paperless"
+    (result,) = art["data"]["results"]
+    assert result["title"] == "vet_invoice"
+    assert result["filename"] == "vet_invoice.pdf"
+    assert result["document_type"] == "Invoice"
+    assert len(result["date"]) == 10
+    assert result["snippet"].startswith("Rabies vaccine administered. ")
+    assert len(result["snippet"]) <= SNIPPET_MAX_CHARS
+
+
+async def test_simba_search_empty(monkeypatch):
+    monkeypatch.setattr(agents, "query_vector_store", AsyncMock(return_value=("", [])))
+
+    msg = await call(agents.simba_search, {"query": "nothing"})
+
+    assert msg.content == ""
+    assert msg.artifact is None
+
+
+async def test_obsidian_search_notes(obsidian, monkeypatch):
+    docs = [
+        Document(
+            page_content="Simba's vet is Dr Smith.",
+            metadata={
+                "source": "obsidian",
+                "filepath": os.path.join(obsidian.vault_path, "pets", "simba.md"),
+                "tags": ["simba"],
+                "created_at": "2026-01-02T10:00:00",
+            },
+        )
+    ]
+    monkeypatch.setattr(
+        agents, "query_vector_store", AsyncMock(return_value=("serialized", docs))
+    )
+
+    msg = await call(agents.obsidian_search_notes, {"query": "vet"})
+
+    assert msg.content == "serialized"
+    art = msg.artifact
+    assert_artifact(art, "search.documents")
+    assert art["data"]["results"] == [
+        {
+            "snippet": "Simba's vet is Dr Smith.",
+            "title": "simba",
+            "path": "pets/simba.md",
+            "date": "2026-01-02",
+        }
+    ]
+
+
+async def test_obsidian_search_notes_error(obsidian, monkeypatch):
+    monkeypatch.setattr(
+        agents, "query_vector_store", AsyncMock(side_effect=Exception("db down"))
+    )
+
+    msg = await call(agents.obsidian_search_notes, {"query": "vet"})
+
+    assert msg.content == "Error searching Obsidian notes: db down"
+    assert msg.artifact is None
+
+
+def test_search_documents_artifact_empty():
+    assert search_documents_artifact("q", "paperless", []) is None
+
+
+@pytest.mark.parametrize(
+    "start,end,expected",
+    [
+        ("2026-10-12", "2026-10-19", "Oct 12–19"),
+        ("2026-10-28", "2026-11-03", "Oct 28–Nov 3"),
+        ("2026-12-28", "2027-01-03", "Dec 28, 2026–Jan 3, 2027"),
+        ("2026-10-12", "2026-10-12", "Oct 12"),
+        ("bad", "2026-10-12", "bad–2026-10-12"),
+    ],
+)
+def test_format_date_range(start, end, expected):
+    assert format_date_range(start, end) == expected
+
+
+async def test_obsidian_note_line_range_retains_full_artifact(obsidian):
+    with open(os.path.join(obsidian.vault_path, "range.md"), "w") as f:
+        f.write("first\nsecond\nthird\nfourth")
+    msg = await call(
+        agents.obsidian_read_note,
+        {"relative_path": "range.md", "start_line": 2, "max_lines": 2},
+    )
+    assert "Content lines 2-3 of 4:\nsecond\nthird\n\n" in msg.content
+    assert "first" not in msg.content
+    assert msg.artifact["data"]["markdown"] == "first\nsecond\nthird\nfourth"
+
+
+@pytest.mark.parametrize(
+    "args", [{"start_line": 0}, {"max_lines": 0}, {"start_line": 99}]
+)
+async def test_obsidian_note_invalid_line_range(obsidian, args):
+    with open(os.path.join(obsidian.vault_path, "range.md"), "w") as f:
+        f.write("first\nsecond")
+    msg = await call(agents.obsidian_read_note, {"relative_path": "range.md", **args})
+    assert msg.artifact is None
+    assert "positive integers" in msg.content or "beyond the end" in msg.content
diff --git a/tests/unit/test_ynab_tool_artifacts.py b/tests/unit/test_ynab_tool_artifacts.py
new file mode 100644
index 0000000..16ff211
--- /dev/null
+++ b/tests/unit/test_ynab_tool_artifacts.py
@@ -0,0 +1,471 @@
+"""Tests for the YNAB tools' content_and_artifact output.
+
+`ensure_fresh` and the `_query` DB helper are mocked; the fake answers each
+query by matching a fragment of its SQL.
+"""
+
+import json
+import re
+from datetime import date
+from decimal import Decimal
+from types import SimpleNamespace
+
+import pytest
+from langchain_core.messages import ToolMessage
+
+from blueprints.ynab import tools
+
+KIND_DATA_KEYS = {
+    "ynab.summary": {
+        "month",
+        "ready_to_assign",
+        "income",
+        "assigned",
+        "spent",
+        "net_worth",
+        "overspent",
+    },
+    "ynab.transactions": {"start_date", "end_date", "count", "total", "transactions"},
+    "ynab.spending_report": {"start_date", "end_date", "group_by", "rows", "total"},
+    "ynab.category_budget": {"month", "groups"},
+}
+
+
+async def call(tool, args=None) -> ToolMessage:
+    """Invoke a tool the way the agent does: with a ToolCall dict."""
+    msg = await tool.ainvoke(
+        {"type": "tool_call", "id": "call-1", "name": tool.name, "args": args or {}}
+    )
+    assert isinstance(msg, ToolMessage)
+    return msg
+
+
+def assert_artifact(artifact, kind, optional=()):
+    assert artifact is not None
+    assert artifact["kind"] == kind
+    assert isinstance(artifact["title"], str) and artifact["title"]
+    assert KIND_DATA_KEYS[kind] <= set(artifact["data"])
+    assert set(artifact["data"]) <= KIND_DATA_KEYS[kind] | set(optional)
+    json.dumps(artifact)
+
+
+def fake_db(monkeypatch, responses: dict, synced=True):
+    """Route `_query` calls to `responses` by SQL fragment; honour LIMIT."""
+    calls = []
+
+    async def fake_query(sql, *params):
+        calls.append((sql, params))
+        for fragment, rows in responses.items():
+            if fragment in sql:
+                limit = re.search(r"LIMIT (\d+)", sql)
+                return rows[: int(limit.group(1))] if limit else rows
+        raise AssertionError(f"unexpected query: {sql}")
+
+    async def fake_ensure_fresh():
+        return SimpleNamespace(budget_name="Home") if synced else None
+
+    monkeypatch.setattr(tools, "_query", fake_query)
+    monkeypatch.setattr(tools, "ensure_fresh", fake_ensure_fresh)
+    monkeypatch.setattr(tools, "_today", lambda: date(2026, 10, 12))
+    return calls
+
+
+# --- ynab_budget_summary ----------------------------------------------------
+
+SUMMARY_DB = {
+    "FROM ynab_months": [
+        {
+            "to_be_budgeted": Decimal("120.50"),
+            "income": Decimal("5000.00"),
+            "budgeted": Decimal("4800.00"),
+            "age_of_money": 42,
+        }
+    ],
+    "mc.balance < 0": [{"name": "Dining Out", "balance": Decimal("-23.10")}],
+    "AS spent": [{"spent": Decimal("3100.25")}],
+    "GROUP BY on_budget": [
+        {"on_budget": True, "total": Decimal("10000.00")},
+        {"on_budget": False, "total": Decimal("-2500.00")},
+    ],
+}
+
+
+async def test_budget_summary(monkeypatch):
+    fake_db(monkeypatch, SUMMARY_DB)
+
+    msg = await call(tools.ynab_budget_summary, {"month": "2026-10"})
+
+    assert msg.content == (
+        "YNAB budget 'Home' for 2026-10:\n"
+        "Ready to Assign: $120.50\n"
+        "Income: $5,000.00\n"
+        "Assigned: $4,800.00\n"
+        "Spent: $3,100.25\n"
+        "Age of money: 42 days\n"
+        "Overspent: Dining Out (-$23.10)\n"
+        "Net worth: $7,500.00 (budget accounts $10,000.00, "
+        "tracking accounts -$2,500.00)"
+    )
+    art = msg.artifact
+    assert_artifact(art, "ynab.summary", optional={"age_of_money"})
+    assert art["title"] == "Budget · October 2026"
+    assert art["data"] == {
+        "month": "2026-10",
+        "ready_to_assign": 120.5,
+        "income": 5000.0,
+        "assigned": 4800.0,
+        "spent": 3100.25,
+        "age_of_money": 42,
+        "net_worth": 7500.0,
+        "overspent": [{"name": "Dining Out", "available": -23.1}],
+    }
+
+
+async def test_budget_summary_without_age_of_money(monkeypatch):
+    db = dict(SUMMARY_DB)
+    db["FROM ynab_months"] = [
+        {**SUMMARY_DB["FROM ynab_months"][0], "age_of_money": None}
+    ]
+    fake_db(monkeypatch, db)
+
+    msg = await call(tools.ynab_budget_summary, {"month": "2026-10"})
+
+    assert "Age of money" not in msg.content
+    assert "age_of_money" not in msg.artifact["data"]
+
+
+async def test_budget_summary_no_month_data(monkeypatch):
+    fake_db(monkeypatch, {"FROM ynab_months": []})
+
+    msg = await call(tools.ynab_budget_summary, {"month": "2026-10"})
+
+    assert msg.content == "No YNAB budget data for 2026-10."
+    assert msg.artifact is None
+
+
+# --- ynab_search_transactions -----------------------------------------------
+
+
+def _txn(i, amount, **extra):
+    return {
+        "id": f"t{i}",
+        "date": date(2026, 10, 12 - i % 10),
+        "amount": Decimal(amount),
+        "memo": None,
+        "approved": True,
+        "account_name": "Checking",
+        "payee_name": "Costco",
+        "category_name": "Groceries",
+        **extra,
+    }
+
+
+TXNS = [
+    _txn(0, "-54.20", memo="milk"),
+    _txn(1, "-12.00", approved=False, payee_name=None, category_name=None),
+    _txn(2, "100.00"),
+]
+TXN_TOTALS = {
+    "count(*) AS n": [
+        {"n": 3, "outflow": Decimal("-66.20"), "inflow": Decimal("100.00")}
+    ],
+}
+
+
+async def test_search_transactions(monkeypatch):
+    calls = fake_db(monkeypatch, {**TXN_TOTALS, "SELECT * FROM lines": TXNS})
+
+    msg = await call(tools.ynab_search_transactions, {"limit": 2})
+
+    assert msg.content == (
+        "Found 3 transactions from 2026-09-12 to 2026-10-12. "
+        "Outflows -$66.20, inflows $100.00.\n"
+        "- 2026-10-12: Costco -$54.20 (Groceries; Checking) — milk\n"
+        "- 2026-10-11: Unknown payee -$12.00 (Uncategorized; Checking) [unapproved]\n"
+        "(Showing 2 most recent of 3)"
+    )
+    assert "LIMIT 500" in calls[-1][0]
+    art = msg.artifact
+    assert_artifact(art, "ynab.transactions")
+    assert art["title"] == "Transactions · Sep 12–Oct 12"
+    data = art["data"]
+    assert data["start_date"] == "2026-09-12"
+    assert data["end_date"] == "2026-10-12"
+    assert data["count"] == 3
+    assert data["total"] == pytest.approx(33.8)
+    # the artifact keeps every row, not just the `limit` shown to the model
+    assert len(data["transactions"]) == 3
+    assert data["transactions"][0] == {
+        "date": "2026-10-12",
+        "payee": "Costco",
+        "category": "Groceries",
+        "account": "Checking",
+        "memo": "milk",
+        "amount": -54.2,
+    }
+    assert "memo" not in data["transactions"][1]
+
+
+async def test_search_transactions_caps_artifact_rows(monkeypatch):
+    many = [_txn(i, "-1.00") for i in range(600)]
+    totals = {"count(*) AS n": [{"n": 600, "outflow": Decimal("-600"), "inflow": 0}]}
+    fake_db(monkeypatch, {**totals, "SELECT * FROM lines": many})
+
+    msg = await call(tools.ynab_search_transactions, {"payee": "costco"})
+
+    assert msg.content.endswith("(Showing 20 most recent of 600)")
+    assert len(msg.artifact["data"]["transactions"]) == tools.ARTIFACT_MAX_TRANSACTIONS
+    assert msg.artifact["data"]["start_date"] is None
+    assert msg.artifact["title"] == "Transactions · through 2026-10-12"
+
+
+async def test_search_transactions_empty(monkeypatch):
+    fake_db(monkeypatch, {"count(*) AS n": [{"n": 0, "outflow": 0, "inflow": 0}]})
+
+    msg = await call(tools.ynab_search_transactions, {})
+
+    assert msg.content == "No transactions found from 2026-09-12 to 2026-10-12."
+    assert msg.artifact is None
+
+
+async def test_search_transactions_bad_date(monkeypatch):
+    fake_db(monkeypatch, {})
+
+    msg = await call(tools.ynab_search_transactions, {"start_date": "nope"})
+
+    assert msg.content == "Dates must be YYYY-MM-DD."
+    assert msg.artifact is None
+
+
+# --- ynab_spending_report ---------------------------------------------------
+
+SPENDING_ROWS = [
+    {"key": "Groceries", "spent": Decimal("400.00"), "n": 10},
+    {"key": "Dining Out", "spent": Decimal("150.50"), "n": 5},
+    {"key": "Gas", "spent": Decimal("60.00"), "n": 2},
+]
+
+
+async def test_spending_report(monkeypatch):
+    fake_db(
+        monkeypatch,
+        {
+            "GROUP BY 1": SPENDING_ROWS,
+            "AS outflows": [
+                {"outflows": Decimal("710.50"), "inflows": Decimal("100.00")}
+            ],
+        },
+    )
+
+    msg = await call(tools.ynab_spending_report, {"top": 2})
+
+    assert msg.content == (
+        "Spending by category from 2026-10-01 to 2026-10-12:\n"
+        "- Total spending (outflows): $710.50\n"
+        "- Inflows (deposits into budget accounts, not spending): $100.00\n"
+        "- Groceries: $400.00 (10 txns)\n"
+        "- Dining Out: $150.50 (5 txns)\n"
+        "- 1 others: $60.00"
+    )
+    art = msg.artifact
+    assert_artifact(art, "ynab.spending_report")
+    assert art["title"] == "Spending by category · Oct 1–12"
+    assert art["data"] == {
+        "start_date": "2026-10-01",
+        "end_date": "2026-10-12",
+        "group_by": "category",
+        "rows": [
+            {"key": "Groceries", "amount": 400.0, "count": 10},
+            {"key": "Dining Out", "amount": 150.5, "count": 5},
+            {"key": "Gas", "amount": 60.0, "count": 2},
+        ],
+        "total": 710.5,
+    }
+
+
+async def test_spending_report_by_month(monkeypatch):
+    rows = [
+        {"key": "2026-09", "spent": Decimal("100"), "n": 1},
+        {"key": "2026-10", "spent": Decimal("200"), "n": 2},
+    ]
+    fake_db(
+        monkeypatch,
+        {
+            "GROUP BY 1": rows,
+            "AS outflows": [
+                {"outflows": Decimal("400.00"), "inflows": Decimal("100.00")}
+            ],
+        },
+    )
+
+    msg = await call(
+        tools.ynab_spending_report,
+        {"group_by": "month", "start_date": "2026-09-01"},
+    )
+
+    assert msg.content.endswith("Monthly average: $200.00")
+    assert msg.artifact["data"]["total"] == 400.0
+    assert [r["key"] for r in msg.artifact["data"]["rows"]] == ["2026-09", "2026-10"]
+
+
+async def test_spending_report_empty_and_invalid(monkeypatch):
+    fake_db(monkeypatch, {"GROUP BY 1": []})
+
+    msg = await call(tools.ynab_spending_report, {})
+    assert msg.content == "No spending found from 2026-10-01 to 2026-10-12."
+    assert msg.artifact is None
+
+    msg = await call(tools.ynab_spending_report, {"group_by": "vibes"})
+    assert msg.content == (
+        "group_by must be one of: category, category_group, payee, account, month."
+    )
+    assert msg.artifact is None
+
+
+# --- ynab_category_budget ---------------------------------------------------
+
+
+def _cat(group, name, budgeted, activity, balance, goal=None):
+    return {
+        "group_name": group,
+        "name": name,
+        "goal_target": Decimal(goal) if goal else None,
+        "budgeted": Decimal(budgeted),
+        "activity": Decimal(activity),
+        "balance": Decimal(balance),
+    }
+
+
+async def test_category_budget(monkeypatch):
+    rows = [
+        _cat("Bills", "Rent", "2000", "-2000", "0"),
+        _cat("Bills", "Unused", "0", "0", "0"),
+        _cat("Food", "Dining Out", "100", "-123.10", "-23.10", goal="150"),
+    ]
+    fake_db(monkeypatch, {"FROM ynab_month_categories mc": rows})
+
+    msg = await call(tools.ynab_category_budget, {"month": "2026-10"})
+
+    assert msg.content == (
+        "Categories for 2026-10:\n"
+        "\nBills\n"
+        "  Rent: assigned $2,000.00, activity -$2,000.00, available $0.00\n"
+        "\nFood\n"
+        "  Dining Out: assigned $100.00, activity -$123.10, available -$23.10, "
+        "goal $150.00 [OVERSPENT]"
+    )
+    art = msg.artifact
+    assert_artifact(art, "ynab.category_budget")
+    assert art["title"] == "Category budget · October 2026"
+    assert art["data"] == {
+        "month": "2026-10",
+        "groups": [
+            {
+                "name": "Bills",
+                "categories": [
+                    {
+                        "name": "Rent",
+                        "assigned": 2000.0,
+                        "activity": -2000.0,
+                        "available": 0.0,
+                    }
+                ],
+            },
+            {
+                "name": "Food",
+                "categories": [
+                    {
+                        "name": "Dining Out",
+                        "assigned": 100.0,
+                        "activity": -123.1,
+                        "available": -23.1,
+                        "goal_target": 150.0,
+                    }
+                ],
+            },
+        ],
+    }
+
+
+async def test_category_budget_all_zero_rows(monkeypatch):
+    rows = [_cat("Bills", "Unused", "0", "0", "0")]
+    fake_db(monkeypatch, {"FROM ynab_month_categories mc": rows})
+
+    msg = await call(tools.ynab_category_budget, {"month": "2026-10"})
+
+    assert msg.content == "Categories for 2026-10:"
+    assert msg.artifact is None
+
+
+async def test_category_budget_empty(monkeypatch):
+    fake_db(monkeypatch, {"FROM ynab_month_categories mc": []})
+
+    msg = await call(tools.ynab_category_budget, {"month": "2026-10"})
+
+    assert msg.content == "No YNAB category data for 2026-10."
+    assert msg.artifact is None
+
+
+# --- shared paths -----------------------------------------------------------
+
+ARTIFACT_TOOLS = [
+    tools.ynab_budget_summary,
+    tools.ynab_search_transactions,
+    tools.ynab_spending_report,
+    tools.ynab_category_budget,
+]
+
+
+@pytest.mark.parametrize("tool", ARTIFACT_TOOLS, ids=lambda t: t.name)
+async def test_not_synced(monkeypatch, tool):
+    fake_db(monkeypatch, {}, synced=False)
+
+    msg = await call(tool)
+
+    assert msg.content == tools.NOT_SYNCED
+    assert msg.artifact is None
+
+
+@pytest.mark.parametrize("tool", ARTIFACT_TOOLS, ids=lambda t: t.name)
+async def test_db_error(monkeypatch, tool):
+    fake_db(monkeypatch, {})
+
+    async def boom(sql, *params):
+        raise RuntimeError("db down")
+
+    monkeypatch.setattr(tools, "_query", boom)
+
+    msg = await call(tool)
+
+    assert msg.content == f"YNAB error in {tool.name}: RuntimeError: db down"
+    assert msg.artifact is None
+
+
+def test_text_only_tools_unchanged():
+    assert tools.ynab_account_balances.response_format == "content"
+    assert tools.ynab_recent_changes.response_format == "content"
+
+
+async def test_spending_report_omits_nonpositive_groups(monkeypatch):
+    rows = SPENDING_ROWS + [
+        {"key": "Uncategorized", "spent": Decimal("-5000"), "n": 1},
+        {"key": "Fully refunded", "spent": Decimal("0"), "n": 2},
+    ]
+    fake_db(
+        monkeypatch,
+        {
+            "GROUP BY 1": rows,
+            "AS outflows": [
+                {"outflows": Decimal("710.50"), "inflows": Decimal("5100.00")}
+            ],
+        },
+    )
+    msg = await call(tools.ynab_spending_report, {})
+    assert "Total spending (outflows): $710.50" in msg.content
+    assert "not spending): $5,100.00" in msg.content
+    assert "Uncategorized" not in msg.content
+    assert "Fully refunded" not in msg.content
+    assert [r["key"] for r in msg.artifact["data"]["rows"]] == [
+        r["key"] for r in SPENDING_ROWS
+    ]
+    assert msg.artifact["data"]["total"] == 710.5
diff --git a/utils/file_extract.py b/utils/file_extract.py
new file mode 100644
index 0000000..9ab738b
--- /dev/null
+++ b/utils/file_extract.py
@@ -0,0 +1,62 @@
+"""Text extraction for files attached to a conversation (PDF, txt, md, csv)."""
+
+import os
+
+import fitz
+
+# Extension -> canonical MIME type for the text-like files we accept.
+FILE_TYPES = {
+    "pdf": "application/pdf",
+    "txt": "text/plain",
+    "md": "text/markdown",
+    "csv": "text/csv",
+}
+_MIME_TO_EXT = {mime: ext for ext, mime in FILE_TYPES.items()}
+_MIME_TO_EXT["text/x-markdown"] = "md"
+
+MAX_ATTACHMENT_CHARS = 12_000
+TRUNCATION_MARKER = "[truncated]"
+
+
+class FileExtractionError(Exception):
+    pass
+
+
+def file_extension(filename: str | None, content_type: str | None) -> str | None:
+    """Return the supported extension for an upload, or None if unsupported.
+
+    Matches on the MIME type first, then falls back to the filename extension
+    (browsers often send .md and .csv as application/octet-stream).
+    """
+    mime = (content_type or "").split(";")[0].strip().lower()
+    if mime in _MIME_TO_EXT:
+        return _MIME_TO_EXT[mime]
+    ext = os.path.splitext(filename or "")[1].lstrip(".").lower()
+    if ext == "markdown":
+        ext = "md"
+    return ext if ext in FILE_TYPES else None
+
+
+def extract_text(data: bytes, ext: str) -> str:
+    """Extract plain text from file bytes. Text files decode as UTF-8 with replacement."""
+    if ext == "pdf":
+        try:
+            with fitz.open(stream=data, filetype="pdf") as doc:
+                return "\n".join(page.get_text() for page in doc).strip()
+        except Exception as e:
+            raise FileExtractionError(f"Could not read PDF: {e}") from e
+    if ext in FILE_TYPES:
+        return data.decode("utf-8", errors="replace").lstrip("")
+    raise FileExtractionError(f"Unsupported file type: {ext}")
+
+
+def cap_text(text: str, limit: int = MAX_ATTACHMENT_CHARS) -> str:
+    if len(text) <= limit:
+        return text
+    return f"{text[:limit]}\n{TRUNCATION_MARKER}"
+
+
+def attachment_block(name: str, text: str) -> str:
+    """Wrap (capped) file text for the user turn sent to the agent."""
+    safe_name = name.replace('"', "'")
+    return f'<attached file "{safe_name}">\n{cap_text(text)}\n</attached>'
diff --git a/utils/s3_client.py b/utils/s3_client.py
index 4d941a5..668ee75 100644
--- a/utils/s3_client.py
+++ b/utils/s3_client.py
@@ -61,3 +61,28 @@ async def delete_image(key: str) -> None:
     async with _get_client() as client:
         await client.delete_object(Bucket=S3_BUCKET_NAME, Key=key)
     logging.info(f"Deleted image from S3: {key}")
+
+
+async def upload_file(
+    file_bytes: bytes, key: str, content_type: str, metadata: dict[str, str]
+) -> str:
+    """Store a non-image object. Metadata values must be ASCII (S3 headers)."""
+    async with _get_client() as client:
+        await client.put_object(
+            Bucket=S3_BUCKET_NAME,
+            Key=key,
+            Body=file_bytes,
+            ContentType=content_type,
+            Metadata=metadata,
+        )
+    logging.info(f"Uploaded file to S3: {key}")
+    return key
+
+
+async def get_file(key: str) -> tuple[bytes, dict[str, str]]:
+    """Return an object's bytes and its user metadata."""
+    async with _get_client() as client:
+        response = await client.get_object(Bucket=S3_BUCKET_NAME, Key=key)
+        body = await response["Body"].read()
+        metadata = response.get("Metadata", {}) or {}
+    return body, metadata