Simplify conversation naming to truncate first message

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

Makefile

@@ -1,8 +1,11 @@
-.PHONY: deploy build up down restart logs migrate migrate-new frontend test
+.PHONY: deploy redeploy build up down restart logs migrate migrate-new frontend test
 
 # Build and deploy
 deploy: build up
 
+redeploy:
+	git pull && $(MAKE) down && $(MAKE) up
+
 build:
 	docker compose build raggr
 

app.py

@@ -1,5 +1,6 @@
 import logging
 import os
+from datetime import timedelta
 
 from dotenv import load_dotenv
 from quart import Quart, jsonify, render_template, request, send_from_directory
@@ -38,6 +39,8 @@ app = Quart(
 )
 
 app.config["JWT_SECRET_KEY"] = os.getenv("JWT_SECRET_KEY", "SECRET_KEY")
+app.config["JWT_ACCESS_TOKEN_EXPIRES"] = timedelta(hours=1)
+app.config["JWT_REFRESH_TOKEN_EXPIRES"] = timedelta(days=30)
 app.config["MAX_CONTENT_LENGTH"] = 10 * 1024 * 1024  # 10 MB upload limit
 jwt = JWTManager(app)
 
@@ -132,17 +135,10 @@ async def get_messages():
             }
         )
 
-    name = conversation.name
-    if len(messages) > 8:
-        name = await blueprints.conversation.logic.rename_conversation(
-            user=user,
-            conversation=conversation,
-        )
-
     return jsonify(
         {
             "id": str(conversation.id),
-            "name": name,
+            "name": conversation.name,
             "messages": messages,
             "created_at": conversation.created_at.isoformat(),
             "updated_at": conversation.updated_at.isoformat(),

blueprints/conversation/__init__.py

@@ -1,4 +1,3 @@
-import datetime
 import json
 import logging
 import uuid
@@ -20,8 +19,8 @@ from .agents import main_agent
 from .logic import (
     add_message_to_conversation,
     get_conversation_by_id,
-    rename_conversation,
 )
+from .memory import get_memories_for_user
 from .models import (
     Conversation,
     PydConversation,
@@ -36,15 +35,27 @@ conversation_blueprint = Blueprint(
 _SYSTEM_PROMPT = SIMBA_SYSTEM_PROMPT
 
 
+async def _build_system_prompt_with_memories(user_id: str) -> str:
+    """Append user memories to the base system prompt."""
+    memories = await get_memories_for_user(user_id)
+    if not memories:
+        return _SYSTEM_PROMPT
+    memory_block = "\n".join(f"- {m}" for m in memories)
+    return f"{_SYSTEM_PROMPT}\n\nUSER MEMORIES (facts the user has asked you to remember):\n{memory_block}"
+
+
 def _build_messages_payload(
-    conversation, query_text: str, image_description: str | None = None
+    conversation,
+    query_text: str,
+    image_description: str | None = None,
+    system_prompt: str | None = None,
 ) -> list:
     recent_messages = (
         conversation.messages[-10:]
         if len(conversation.messages) > 10
         else conversation.messages
     )
-    messages_payload = [{"role": "system", "content": _SYSTEM_PROMPT}]
+    messages_payload = [{"role": "system", "content": system_prompt or _SYSTEM_PROMPT}]
     for msg in recent_messages[:-1]:  # Exclude the message we just added
         role = "user" if msg.speaker == "user" else "assistant"
         text = msg.text
@@ -80,10 +91,14 @@ async def query():
         user=user,
     )
 
-    messages_payload = _build_messages_payload(conversation, query)
+    system_prompt = await _build_system_prompt_with_memories(str(user.id))
+    messages_payload = _build_messages_payload(
+        conversation, query, system_prompt=system_prompt
+    )
     payload = {"messages": messages_payload}
+    agent_config = {"configurable": {"user_id": str(user.id)}}
 
-    response = await main_agent.ainvoke(payload)
+    response = await main_agent.ainvoke(payload, config=agent_config)
     message = response.get("messages", [])[-1].content
     await add_message_to_conversation(
         conversation=conversation,
@@ -163,15 +178,19 @@ async def stream_query():
             logging.error(f"Failed to analyze image: {e}")
             image_description = "[Image could not be analyzed]"
 
+    system_prompt = await _build_system_prompt_with_memories(str(user.id))
     messages_payload = _build_messages_payload(
-        conversation, query_text or "", image_description
+        conversation, query_text or "", image_description, system_prompt=system_prompt
     )
     payload = {"messages": messages_payload}
+    agent_config = {"configurable": {"user_id": str(user.id)}}
 
     async def event_generator():
         final_message = None
         try:
-            async for event in main_agent.astream_events(payload, version="v2"):
+            async for event in main_agent.astream_events(
+                payload, version="v2", config=agent_config
+            ):
                 event_type = event.get("event")
 
                 if event_type == "on_tool_start":
@@ -221,8 +240,6 @@ async def stream_query():
 @jwt_refresh_token_required
 async def get_conversation(conversation_id: str):
     conversation = await Conversation.get(id=conversation_id)
-    current_user_uuid = get_jwt_identity()
-    user = await blueprints.users.models.User.get(id=current_user_uuid)
     await conversation.fetch_related("messages")
 
     # Manually serialize the conversation with messages
@@ -237,18 +254,10 @@ async def get_conversation(conversation_id: str):
                 "image_key": msg.image_key,
             }
         )
-    name = conversation.name
-    if len(messages) > 8 and "datetime" in name.lower():
-        name = await rename_conversation(
-            user=user,
-            conversation=conversation,
-        )
-        print(name)
-
     return jsonify(
         {
             "id": str(conversation.id),
-            "name": name,
+            "name": conversation.name,
             "messages": messages,
             "created_at": conversation.created_at.isoformat(),
             "updated_at": conversation.updated_at.isoformat(),
@@ -262,7 +271,7 @@ async def create_conversation():
     user_uuid = get_jwt_identity()
     user = await blueprints.users.models.User.get(id=user_uuid)
     conversation = await Conversation.create(
-        name=f"{user.username} {datetime.datetime.now().timestamp}",
+        name="New Conversation",
         user=user,
     )
 
@@ -275,7 +284,7 @@ async def create_conversation():
 async def get_all_conversations():
     user_uuid = get_jwt_identity()
     user = await blueprints.users.models.User.get(id=user_uuid)
-    conversations = Conversation.filter(user=user)
+    conversations = Conversation.filter(user=user).order_by("-updated_at")
     serialized_conversations = await PydListConversation.from_queryset(conversations)
 
     return jsonify(serialized_conversations.model_dump())

blueprints/conversation/agents.py

@@ -5,9 +5,11 @@ from dotenv import load_dotenv
 from langchain.agents import create_agent
 from langchain.chat_models import BaseChatModel
 from langchain.tools import tool
+from langchain_core.runnables import RunnableConfig
 from langchain_openai import ChatOpenAI
 from tavily import AsyncTavilyClient
 
+from blueprints.conversation.memory import save_memory
 from blueprints.rag.logic import query_vector_store
 from utils.obsidian_service import ObsidianService
 from utils.ynab_service import YNABService
@@ -589,8 +591,35 @@ async def obsidian_create_task(
         return f"Error creating task: {str(e)}"
 
 
+@tool
+async def save_user_memory(content: str, config: RunnableConfig) -> str:
+    """Save a fact or preference about the user for future conversations.
+
+    Use this tool when the user:
+    - Explicitly asks you to remember something ("remember that...", "keep in mind...")
+    - Shares a personal preference that would be useful in future conversations
+      (e.g., "I prefer metric units", "my cat's name is Luna")
+    - Tells you a meaningful personal fact (e.g., "I'm allergic to peanuts")
+
+    Do NOT save:
+    - Trivial or ephemeral info (e.g., "I'm tired today")
+    - Information already in the system prompt or documents
+    - Conversation-specific context that won't matter later
+
+    Args:
+        content: A concise statement of the fact or preference to remember.
+                 Write it as a standalone sentence (e.g., "User prefers dark mode"
+                 rather than "likes dark mode").
+
+    Returns:
+        Confirmation that the memory was saved.
+    """
+    user_id = config["configurable"]["user_id"]
+    return await save_memory(user_id=user_id, content=content)
+
+
 # Create tools list based on what's available
-tools = [get_current_date, simba_search, web_search]
+tools = [get_current_date, simba_search, web_search, save_user_memory]
 if ynab_enabled:
     tools.extend(
         [

blueprints/conversation/logic.py

@@ -1,9 +1,8 @@
 import tortoise.exceptions
-from langchain_openai import ChatOpenAI
 
 import blueprints.users.models
 
-from .models import Conversation, ConversationMessage, RenameConversationOutputSchema
+from .models import Conversation, ConversationMessage
 
 
 async def create_conversation(name: str = "") -> Conversation:
@@ -19,6 +18,12 @@ async def add_message_to_conversation(
     image_key: str | None = None,
 ) -> ConversationMessage:
     print(conversation, message, speaker)
+
+    # Name the conversation after the first user message
+    if speaker == "user" and not await conversation.messages.all().exists():
+        conversation.name = message[:100]
+        await conversation.save()
+
     message = await ConversationMessage.create(
         text=message,
         speaker=speaker,
@@ -61,22 +66,3 @@ async def get_conversation_transcript(
         messages.append(f"{message.speaker} at {message.created_at}: {message.text}")
 
     return "\n".join(messages)
-
-
-async def rename_conversation(
-    user: blueprints.users.models.User,
-    conversation: Conversation,
-) -> str:
-    messages: str = await get_conversation_transcript(
-        user=user, conversation=conversation
-    )
-
-    llm = ChatOpenAI(model="gpt-4o-mini")
-    structured_llm = llm.with_structured_output(RenameConversationOutputSchema)
-
-    prompt = f"Summarize the following conversation into a sassy one-liner title:\n\n{messages}"
-    response = structured_llm.invoke(prompt)
-    new_name: str = response.get("title", "")
-    conversation.name = new_name
-    await conversation.save()
-    return new_name

blueprints/conversation/memory.py

@@ -0,0 +1,19 @@
+from .models import UserMemory
+
+
+async def get_memories_for_user(user_id: str) -> list[str]:
+    """Return all memory content strings for a user, ordered by most recently updated."""
+    memories = await UserMemory.filter(user_id=user_id).order_by("-updated_at")
+    return [m.content for m in memories]
+
+
+async def save_memory(user_id: str, content: str) -> str:
+    """Save a new memory or touch an existing one (exact-match dedup)."""
+    existing = await UserMemory.filter(user_id=user_id, content=content).first()
+    if existing:
+        existing.updated_at = None  # auto_now=True will refresh it on save
+        await existing.save(update_fields=["updated_at"])
+        return "Memory already exists (refreshed)."
+
+    await UserMemory.create(user_id=user_id, content=content)
+    return "Memory saved."

blueprints/conversation/models.py

@@ -1,5 +1,4 @@
 import enum
-from dataclasses import dataclass
 
 from tortoise import fields
 from tortoise.contrib.pydantic import (
@@ -9,12 +8,6 @@ from tortoise.contrib.pydantic import (
 from tortoise.models import Model
 
 
-@dataclass
-class RenameConversationOutputSchema:
-    title: str
-    justification: str
-
-
 class Speaker(enum.Enum):
     USER = "user"
     SIMBA = "simba"
@@ -47,6 +40,17 @@ class ConversationMessage(Model):
         table = "conversation_messages"
 
 
+class UserMemory(Model):
+    id = fields.UUIDField(primary_key=True)
+    user = fields.ForeignKeyField("models.User", related_name="memories")
+    content = fields.TextField()
+    created_at = fields.DatetimeField(auto_now_add=True)
+    updated_at = fields.DatetimeField(auto_now=True)
+
+    class Meta:
+        table = "user_memories"
+
+
 PydConversationMessage = pydantic_model_creator(ConversationMessage)
 PydConversation = pydantic_model_creator(
     Conversation, name="Conversation", allow_cycles=True, exclude=("user",)

blueprints/conversation/prompts.py

@@ -54,4 +54,7 @@ You have access to Ryan's daily journal notes. Each note lives at journal/YYYY/Y
 - Use journal_get_tasks to list tasks (done/pending) for today or a specific date
 - Use journal_add_task to add a new task to today's (or a given date's) note
 - Use journal_complete_task to check off a task as done
-Use these tools when Ryan asks about today's tasks, wants to add something to his list, or wants to mark a task complete."""
+Use these tools when Ryan asks about today's tasks, wants to add something to his list, or wants to mark a task complete.
+
+USER MEMORY:
+You can remember facts about the user across conversations using the save_user_memory tool. When a user explicitly asks you to remember something, or shares a meaningful preference or personal fact, save it. Saved memories will automatically appear at the end of this prompt in future conversations under "USER MEMORIES"."""

blueprints/users/oidc_service.py

@@ -35,7 +35,7 @@ class OIDCUserService:
                 claims.get("preferred_username") or claims.get("name") or user.username
             )
             # Update LDAP groups from claims
-            user.ldap_groups = claims.get("groups", [])
+            user.ldap_groups = claims.get("groups") or []
             await user.save()
             return user
 
@@ -48,7 +48,7 @@ class OIDCUserService:
                 user.oidc_subject = oidc_subject
                 user.auth_provider = "oidc"
                 user.password = None  # Clear password
-                user.ldap_groups = claims.get("groups", [])
+                user.ldap_groups = claims.get("groups") or []
                 await user.save()
                 return user
 
@@ -61,7 +61,7 @@ class OIDCUserService:
         )
 
         # Extract LDAP groups from claims
-        groups = claims.get("groups", [])
+        groups = claims.get("groups") or []
 
         user = await User.create(
             id=uuid4(),

migrations/models/5_20260409215154_add_user_memories.py

@@ -0,0 +1,112 @@
+from tortoise import BaseDBAsyncClient
+
+RUN_IN_TRANSACTION = True
+
+
+async def upgrade(db: BaseDBAsyncClient) -> str:
+    return """
+        CREATE TABLE IF NOT EXISTS "user_memories" (
+    "id" UUID NOT NULL PRIMARY KEY,
+    "content" TEXT NOT NULL,
+    "created_at" TIMESTAMPTZ NOT NULL DEFAULT CURRENT_TIMESTAMP,
+    "updated_at" TIMESTAMPTZ NOT NULL DEFAULT CURRENT_TIMESTAMP,
+    "user_id" UUID NOT NULL REFERENCES "users" ("id") ON DELETE CASCADE
+);
+        CREATE TABLE IF NOT EXISTS "email_accounts" (
+    "id" UUID NOT NULL PRIMARY KEY,
+    "email_address" VARCHAR(255) NOT NULL UNIQUE,
+    "display_name" VARCHAR(255),
+    "imap_host" VARCHAR(255) NOT NULL,
+    "imap_port" INT NOT NULL DEFAULT 993,
+    "imap_username" VARCHAR(255) NOT NULL,
+    "imap_password" TEXT NOT NULL,
+    "is_active" BOOL NOT NULL DEFAULT True,
+    "last_error" TEXT,
+    "created_at" TIMESTAMPTZ NOT NULL DEFAULT CURRENT_TIMESTAMP,
+    "updated_at" TIMESTAMPTZ NOT NULL DEFAULT CURRENT_TIMESTAMP,
+    "user_id" UUID NOT NULL REFERENCES "users" ("id") ON DELETE CASCADE
+);
+COMMENT ON TABLE "email_accounts" IS 'Email account configuration for IMAP connections.';
+        CREATE TABLE IF NOT EXISTS "emails" (
+    "id" UUID NOT NULL PRIMARY KEY,
+    "message_id" VARCHAR(255) NOT NULL UNIQUE,
+    "subject" VARCHAR(500) NOT NULL,
+    "from_address" VARCHAR(255) NOT NULL,
+    "to_address" TEXT NOT NULL,
+    "date" TIMESTAMPTZ NOT NULL,
+    "body_text" TEXT,
+    "body_html" TEXT,
+    "chromadb_doc_id" VARCHAR(255),
+    "created_at" TIMESTAMPTZ NOT NULL DEFAULT CURRENT_TIMESTAMP,
+    "expires_at" TIMESTAMPTZ NOT NULL,
+    "account_id" UUID NOT NULL REFERENCES "email_accounts" ("id") ON DELETE CASCADE
+);
+CREATE INDEX IF NOT EXISTS "idx_emails_message_981ddd" ON "emails" ("message_id");
+COMMENT ON TABLE "emails" IS 'Email message metadata and content.';
+        CREATE TABLE IF NOT EXISTS "email_sync_status" (
+    "id" UUID NOT NULL PRIMARY KEY,
+    "last_sync_date" TIMESTAMPTZ,
+    "last_message_uid" INT NOT NULL DEFAULT 0,
+    "message_count" INT NOT NULL DEFAULT 0,
+    "consecutive_failures" INT NOT NULL DEFAULT 0,
+    "last_failure_date" TIMESTAMPTZ,
+    "updated_at" TIMESTAMPTZ NOT NULL DEFAULT CURRENT_TIMESTAMP,
+    "account_id" UUID NOT NULL REFERENCES "email_accounts" ("id") ON DELETE CASCADE
+);
+COMMENT ON TABLE "email_sync_status" IS 'Tracks sync progress and state per email account.';"""
+
+
+async def downgrade(db: BaseDBAsyncClient) -> str:
+    return """
+        DROP TABLE IF EXISTS "user_memories";
+        DROP TABLE IF EXISTS "email_accounts";
+        DROP TABLE IF EXISTS "emails";
+        DROP TABLE IF EXISTS "email_sync_status";"""
+
+
+MODELS_STATE = (
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+    "AxhSAWmX+XWMolGaGw+Q6d7aDZpJ94k26UlOeppDR5WM8sD2vfSQ31z8JqYWqbE10RPUc1"
+    "R8uCZrRoU5kv5xU/S1+TEUcT+KTJMjvhIcVho3j9Xflt8+KH6QmTujzoPcQHc2BplAAxal"
+    "5PAPfyGbfCj3MXfxin+OPcB/sozt4O3Z19FKfENzZ2f7x8+x8fHBMe"
+)

raggr-frontend/src/components/ChatScreen.tsx

@@ -1,4 +1,4 @@
-import { useEffect, useState, useRef } from "react";
+import { useCallback, useEffect, useState, useRef } from "react";
 import { LogOut, Shield, PanelLeftClose, PanelLeftOpen, Menu, X } from "lucide-react";
 import { conversationService } from "../api/conversationService";
 import { userService } from "../api/userService";
@@ -63,9 +63,13 @@ export const ChatScreen = ({ setAuthenticated }: ChatScreenProps) => {
   const abortControllerRef = useRef<AbortController | null>(null);
   const simbaAnswers = ["meow.", "hiss...", "purrrrrr", "yowOWROWWowowr"];
 
-  const scrollToBottom = () => {
-    messagesEndRef.current?.scrollIntoView({ behavior: "smooth" });
-  };
+  const scrollToBottom = useCallback(() => {
+    requestAnimationFrame(() => {
+      messagesEndRef.current?.scrollIntoView({
+        behavior: isLoading ? "instant" : "smooth",
+      });
+    });
+  }, [isLoading]);
 
   useEffect(() => {
     isMountedRef.current = true;
@@ -130,7 +134,7 @@ export const ChatScreen = ({ setAuthenticated }: ChatScreenProps) => {
     load();
   }, [selectedConversation?.id]);
 
-  const handleQuestionSubmit = async () => {
+  const handleQuestionSubmit = useCallback(async () => {
     if ((!query.trim() && !pendingImage) || isLoading) return;
 
     let activeConversation = selectedConversation;
@@ -214,19 +218,22 @@ export const ChatScreen = ({ setAuthenticated }: ChatScreenProps) => {
       if (isMountedRef.current) setIsLoading(false);
       abortControllerRef.current = null;
     }
-  };
+  }, [query, pendingImage, isLoading, selectedConversation, simbaMode, messages, setAuthenticated]);
 
-  const handleQueryChange = (event: React.ChangeEvent<HTMLTextAreaElement>) => {
+  const handleQueryChange = useCallback((event: React.ChangeEvent<HTMLTextAreaElement>) => {
     setQuery(event.target.value);
-  };
+  }, []);
 
-  const handleKeyDown = (event: React.ChangeEvent<HTMLTextAreaElement>) => {
+  const handleKeyDown = useCallback((event: React.ChangeEvent<HTMLTextAreaElement>) => {
     const kev = event as unknown as React.KeyboardEvent<HTMLTextAreaElement>;
     if (kev.key === "Enter" && !kev.shiftKey) {
       kev.preventDefault();
       handleQuestionSubmit();
     }
-  };
+  }, [handleQuestionSubmit]);
+
+  const handleImageSelect = useCallback((file: File) => setPendingImage(file), []);
+  const handleClearImage = useCallback(() => setPendingImage(null), []);
 
   const handleLogout = () => {
     localStorage.removeItem("access_token");
@@ -380,8 +387,8 @@ export const ChatScreen = ({ setAuthenticated }: ChatScreenProps) => {
                 setSimbaMode={setSimbaMode}
                 isLoading={isLoading}
                 pendingImage={pendingImage}
-                onImageSelect={(file) => setPendingImage(file)}
-                onClearImage={() => setPendingImage(null)}
+                onImageSelect={handleImageSelect}
+                onClearImage={handleClearImage}
               />
             </div>
           </div>
@@ -416,7 +423,7 @@ export const ChatScreen = ({ setAuthenticated }: ChatScreenProps) => {
               </div>
             </div>
 
-            <footer className="border-t border-sand-light/40 bg-cream/80 backdrop-blur-sm">
+            <footer className="border-t border-sand-light/40 bg-cream">
               <div className="max-w-2xl mx-auto px-4 py-3">
                 <MessageInput
                   query={query}
@@ -425,6 +432,9 @@ export const ChatScreen = ({ setAuthenticated }: ChatScreenProps) => {
                   handleQuestionSubmit={handleQuestionSubmit}
                   setSimbaMode={setSimbaMode}
                   isLoading={isLoading}
+                  pendingImage={pendingImage}
+                  onImageSelect={(file) => setPendingImage(file)}
+                  onClearImage={() => setPendingImage(null)}
                 />
               </div>
             </footer>

raggr-frontend/src/components/MessageInput.tsx

@@ -1,4 +1,4 @@
-import { useRef, useState } from "react";
+import React, { useEffect, useMemo, useRef, useState } from "react";
 import { ArrowUp, ImagePlus, X } from "lucide-react";
 import { cn } from "../lib/utils";
 import { Textarea } from "./ui/textarea";
@@ -15,7 +15,7 @@ type MessageInputProps = {
   onClearImage: () => void;
 };
 
-export const MessageInput = ({
+export const MessageInput = React.memo(({
   query,
   handleKeyDown,
   handleQueryChange,
@@ -29,6 +29,18 @@ export const MessageInput = ({
   const [simbaMode, setLocalSimbaMode] = useState(false);
   const fileInputRef = useRef<HTMLInputElement>(null);
 
+  // Create blob URL once per file, revoke on cleanup
+  const previewUrl = useMemo(
+    () => (pendingImage ? URL.createObjectURL(pendingImage) : null),
+    [pendingImage],
+  );
+
+  useEffect(() => {
+    return () => {
+      if (previewUrl) URL.revokeObjectURL(previewUrl);
+    };
+  }, [previewUrl]);
+
   const toggleSimbaMode = () => {
     const next = !simbaMode;
     setLocalSimbaMode(next);
@@ -59,7 +71,7 @@ export const MessageInput = ({
         <div className="px-3 pt-3">
           <div className="relative inline-block">
             <img
-              src={URL.createObjectURL(pendingImage)}
+              src={previewUrl!}
               alt="Pending upload"
               className="h-20 rounded-lg object-cover border border-sand"
             />
@@ -145,4 +157,4 @@ export const MessageInput = ({
       </div>
     </div>
   );
-};
+});