Merge pull request 'Order conversations by recency and auto-name from first message' (#24) from feat/conversation-ordering-and-naming into main

Reviewed-on: #24

CLAUDE.md

@@ -91,6 +91,15 @@ docker compose up -d
 
 **Auth Flow**: LLDAP → Authelia (OIDC) → Backend JWT → Frontend localStorage
 
+## Testing
+
+Always run `make test` before pushing code to ensure all tests pass.
+
+```bash
+make test       # Run tests
+make test-cov   # Run tests with coverage
+```
+
 ## Key Patterns
 
 - All endpoints are async (`async def`)

Makefile

@@ -0,0 +1,44 @@
+.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
+
+up:
+	docker compose up -d
+
+down:
+	docker compose down
+
+restart:
+	docker compose restart raggr
+
+logs:
+	docker compose logs -f raggr
+
+# Database migrations
+migrate:
+	docker compose exec raggr aerich upgrade
+
+migrate-new:
+	@read -p "Migration name: " name; \
+	docker compose exec raggr aerich migrate --name $$name
+
+migrate-history:
+	docker compose exec raggr aerich history
+
+# Tests
+test:
+	pytest tests/ -v
+
+test-cov:
+	pytest tests/ -v --cov
+
+# Frontend
+frontend:
+	cd raggr-frontend && yarn install && yarn build

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)
 

blueprints/conversation/__init__.py

@@ -3,7 +3,7 @@ import json
 import logging
 import uuid
 
-from quart import Blueprint, Response, jsonify, make_response, request
+from quart import Blueprint, jsonify, make_response, request
 from quart_jwt_extended import (
     get_jwt_identity,
     jwt_refresh_token_required,
@@ -12,6 +12,7 @@ from quart_jwt_extended import (
 import blueprints.users.models
 from utils.image_process import analyze_user_image
 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_image as s3_get_image
 from utils.s3_client import upload_image as s3_upload_image
 
@@ -122,27 +123,14 @@ async def upload_image():
 
     await s3_upload_image(processed_bytes, key, output_content_type)
 
-    return jsonify(
-        {
-            "image_key": key,
-            "image_url": f"/api/conversation/image/{key}",
-        }
-    )
+    return jsonify({"image_key": key})
 
 
 @conversation_blueprint.get("/image/<path:image_key>")
 @jwt_refresh_token_required
 async def serve_image(image_key: str):
-    try:
-        image_bytes, content_type = await s3_get_image(image_key)
-    except Exception:
-        return jsonify({"error": "Image not found"}), 404
-
-    return Response(
-        image_bytes,
-        content_type=content_type,
-        headers={"Cache-Control": "private, max-age=3600"},
-    )
+    url = await s3_presigned_url(image_key)
+    return jsonify({"url": url})
 
 
 @conversation_blueprint.post("/stream-query")
@@ -287,7 +275,7 @@ 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/logic.py

@@ -19,6 +19,12 @@ 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,

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(),

docker-compose.yml

@@ -61,6 +61,7 @@ services:
       - S3_BUCKET_NAME=${S3_BUCKET_NAME:-asksimba-images}
       - S3_REGION=${S3_REGION:-garage}
       - OLLAMA_HOST=${OLLAMA_HOST:-http://localhost:11434}
+      - FERNET_KEY=${FERNET_KEY}
     depends_on:
       postgres:
         condition: service_healthy

pyproject.toml

@@ -42,6 +42,17 @@ dependencies = [
     "aioboto3>=13.0.0",
 ]
 
+[project.optional-dependencies]
+test = [
+    "pytest>=8.0.0",
+    "pytest-asyncio>=0.25.0",
+    "pytest-cov>=6.0.0",
+]
+
+[tool.pytest.ini_options]
+testpaths = ["tests"]
+asyncio_mode = "auto"
+
 [tool.aerich]
 tortoise_orm = "config.db.TORTOISE_CONFIG"
 location = "./migrations"

raggr-frontend/src/api/conversationService.ts

@@ -125,7 +125,7 @@ class ConversationService {
   async uploadImage(
     file: File,
     conversationId: string,
-  ): Promise<{ image_key: string; image_url: string }> {
+  ): Promise<{ image_key: string }> {
     const formData = new FormData();
     formData.append("file", file);
     formData.append("conversation_id", conversationId);
@@ -147,8 +147,15 @@ class ConversationService {
     return await response.json();
   }
 
-  getImageUrl(imageKey: string): string {
-    return `/api/conversation/image/${imageKey}`;
+  async getPresignedImageUrl(imageKey: string): Promise<string> {
+    const response = await userService.fetchWithRefreshToken(
+      `${this.conversationBaseUrl}/image/${imageKey}`,
+    );
+    if (!response.ok) {
+      throw new Error("Failed to get image URL");
+    }
+    const data = await response.json();
+    return data.url;
   }
 
   async streamQuery(

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>
   );
-};
+});

raggr-frontend/src/components/QuestionBubble.tsx

@@ -1,3 +1,4 @@
+import { useEffect, useState } from "react";
 import { cn } from "../lib/utils";
 import { conversationService } from "../api/conversationService";
 
@@ -7,6 +8,20 @@ type QuestionBubbleProps = {
 };
 
 export const QuestionBubble = ({ text, image_key }: QuestionBubbleProps) => {
+  const [imageUrl, setImageUrl] = useState<string | null>(null);
+  const [imageError, setImageError] = useState(false);
+
+  useEffect(() => {
+    if (!image_key) return;
+    conversationService
+      .getPresignedImageUrl(image_key)
+      .then(setImageUrl)
+      .catch((err) => {
+        console.error("Failed to load image:", err);
+        setImageError(true);
+      });
+  }, [image_key]);
+
   return (
     <div className="flex justify-end message-enter">
       <div
@@ -17,9 +32,15 @@ export const QuestionBubble = ({ text, image_key }: QuestionBubbleProps) => {
           "shadow-sm shadow-leaf/10",
         )}
       >
-        {image_key && (
+        {imageError && (
+          <div className="flex items-center gap-2 text-xs text-charcoal/50 bg-charcoal/5 rounded-xl px-3 py-2 mb-2">
+            <span>🖼️</span>
+            <span>Image failed to load</span>
+          </div>
+        )}
+        {imageUrl && (
           <img
-            src={conversationService.getImageUrl(image_key)}
+            src={imageUrl}
             alt="Uploaded image"
             className="max-w-full rounded-xl mb-2"
           />

tests/conftest.py

@@ -0,0 +1,11 @@
+import os
+import sys
+
+# Ensure project root is on the path so imports work
+sys.path.insert(0, os.path.join(os.path.dirname(__file__), ".."))
+
+# Set FERNET_KEY for tests that import email models (EncryptedTextField needs it at import time)
+if "FERNET_KEY" not in os.environ:
+    from cryptography.fernet import Fernet
+
+    os.environ["FERNET_KEY"] = Fernet.generate_key().decode()

tests/unit/test_chunker.py

@@ -0,0 +1,139 @@
+"""Tests for text preprocessing functions in utils/chunker.py."""
+
+from utils.chunker import (
+    remove_headers_footers,
+    remove_special_characters,
+    remove_repeated_substrings,
+    remove_extra_spaces,
+    preprocess_text,
+)
+
+
+class TestRemoveHeadersFooters:
+    def test_removes_default_header(self):
+        text = "Header Line\nActual content here"
+        result = remove_headers_footers(text)
+        assert "Header" not in result
+        assert "Actual content here" in result
+
+    def test_removes_default_footer(self):
+        text = "Actual content\nFooter Line"
+        result = remove_headers_footers(text)
+        assert "Footer" not in result
+        assert "Actual content" in result
+
+    def test_custom_patterns(self):
+        text = "PAGE 1\nContent\nCopyright 2024"
+        result = remove_headers_footers(
+            text,
+            header_patterns=[r"^PAGE \d+$"],
+            footer_patterns=[r"^Copyright.*$"],
+        )
+        assert "PAGE 1" not in result
+        assert "Copyright" not in result
+        assert "Content" in result
+
+    def test_no_match_preserves_text(self):
+        text = "Just normal content"
+        result = remove_headers_footers(text)
+        assert result == "Just normal content"
+
+    def test_empty_string(self):
+        assert remove_headers_footers("") == ""
+
+
+class TestRemoveSpecialCharacters:
+    def test_removes_special_chars(self):
+        text = "Hello @world #test $100"
+        result = remove_special_characters(text)
+        assert "@" not in result
+        assert "#" not in result
+        assert "$" not in result
+
+    def test_preserves_allowed_chars(self):
+        text = "Hello, world! How's it going? Yes-no."
+        result = remove_special_characters(text)
+        assert "," in result
+        assert "!" in result
+        assert "'" in result
+        assert "?" in result
+        assert "-" in result
+        assert "." in result
+
+    def test_custom_pattern(self):
+        text = "keep @this but not #that"
+        result = remove_special_characters(text, special_chars=r"[#]")
+        assert "@this" in result
+        assert "#" not in result
+
+    def test_empty_string(self):
+        assert remove_special_characters("") == ""
+
+
+class TestRemoveRepeatedSubstrings:
+    def test_collapses_dots(self):
+        text = "Item.....Value"
+        result = remove_repeated_substrings(text)
+        assert result == "Item.Value"
+
+    def test_single_dot_preserved(self):
+        text = "End of sentence."
+        result = remove_repeated_substrings(text)
+        assert result == "End of sentence."
+
+    def test_custom_pattern(self):
+        text = "hello---world"
+        result = remove_repeated_substrings(text, pattern=r"-{2,}")
+        # Function always replaces matched pattern with "."
+        assert result == "hello.world"
+
+    def test_empty_string(self):
+        assert remove_repeated_substrings("") == ""
+
+
+class TestRemoveExtraSpaces:
+    def test_collapses_multiple_blank_lines(self):
+        text = "Line 1\n\n\n\nLine 2"
+        result = remove_extra_spaces(text)
+        # After collapsing newlines to \n\n, then \s+ collapses everything to single spaces
+        assert "\n\n\n" not in result
+
+    def test_collapses_multiple_spaces(self):
+        text = "Hello    world"
+        result = remove_extra_spaces(text)
+        assert result == "Hello world"
+
+    def test_strips_whitespace(self):
+        text = "  Hello world  "
+        result = remove_extra_spaces(text)
+        assert result == "Hello world"
+
+    def test_empty_string(self):
+        assert remove_extra_spaces("") == ""
+
+
+class TestPreprocessText:
+    def test_full_pipeline(self):
+        text = "Header Info\nHello @world...  with   spaces\nFooter Info"
+        result = preprocess_text(text)
+        assert "Header" not in result
+        assert "Footer" not in result
+        assert "@" not in result
+        assert "..." not in result
+        assert "   " not in result
+
+    def test_preserves_meaningful_content(self):
+        text = "The cat weighs 10 pounds."
+        result = preprocess_text(text)
+        assert "cat" in result
+        assert "10" in result
+        assert "pounds" in result
+
+    def test_empty_string(self):
+        assert preprocess_text("") == ""
+
+    def test_already_clean(self):
+        text = "Simple clean text here."
+        result = preprocess_text(text)
+        assert "Simple" in result
+        assert "clean" in result

tests/unit/test_crypto_service.py

@@ -0,0 +1,91 @@
+"""Tests for encryption/decryption in blueprints/email/crypto_service.py."""
+
+import os
+from unittest.mock import patch
+
+import pytest
+from cryptography.fernet import Fernet
+
+
+# Generate a valid key for testing
+TEST_FERNET_KEY = Fernet.generate_key().decode()
+
+
+class TestEncryptedTextField:
+    @pytest.fixture
+    def field(self):
+        with patch.dict(os.environ, {"FERNET_KEY": TEST_FERNET_KEY}):
+            from blueprints.email.crypto_service import EncryptedTextField
+
+            return EncryptedTextField()
+
+    def test_encrypt_decrypt_roundtrip(self, field):
+        original = "my secret password"
+        encrypted = field.to_db_value(original, None)
+        decrypted = field.to_python_value(encrypted)
+        assert decrypted == original
+        assert encrypted != original
+
+    def test_none_passthrough(self, field):
+        assert field.to_db_value(None, None) is None
+        assert field.to_python_value(None) is None
+
+    def test_unicode_roundtrip(self, field):
+        original = "Hello 世界 🐱"
+        encrypted = field.to_db_value(original, None)
+        decrypted = field.to_python_value(encrypted)
+        assert decrypted == original
+
+    def test_empty_string_roundtrip(self, field):
+        encrypted = field.to_db_value("", None)
+        decrypted = field.to_python_value(encrypted)
+        assert decrypted == ""
+
+    def test_long_text_roundtrip(self, field):
+        original = "x" * 10000
+        encrypted = field.to_db_value(original, None)
+        decrypted = field.to_python_value(encrypted)
+        assert decrypted == original
+
+    def test_different_encryptions_differ(self, field):
+        """Fernet includes a timestamp, so two encryptions of the same value differ."""
+        e1 = field.to_db_value("same", None)
+        e2 = field.to_db_value("same", None)
+        assert e1 != e2  # Different ciphertexts
+        assert field.to_python_value(e1) == field.to_python_value(e2) == "same"
+
+    def test_wrong_key_fails(self, field):
+        encrypted = field.to_db_value("secret", None)
+
+        # Create a field with a different key
+        other_key = Fernet.generate_key().decode()
+        with patch.dict(os.environ, {"FERNET_KEY": other_key}):
+            from blueprints.email.crypto_service import EncryptedTextField
+
+            other_field = EncryptedTextField()
+
+        with pytest.raises(Exception):
+            other_field.to_python_value(encrypted)
+
+
+class TestValidateFernetKey:
+    def test_valid_key(self):
+        with patch.dict(os.environ, {"FERNET_KEY": TEST_FERNET_KEY}):
+            from blueprints.email.crypto_service import validate_fernet_key
+
+            validate_fernet_key()  # Should not raise
+
+    def test_missing_key(self):
+        with patch.dict(os.environ, {}, clear=True):
+            os.environ.pop("FERNET_KEY", None)
+            from blueprints.email.crypto_service import validate_fernet_key
+
+            with pytest.raises(ValueError, match="not set"):
+                validate_fernet_key()
+
+    def test_invalid_key(self):
+        with patch.dict(os.environ, {"FERNET_KEY": "not-a-valid-key"}):
+            from blueprints.email.crypto_service import validate_fernet_key
+
+            with pytest.raises(ValueError, match="validation failed"):
+                validate_fernet_key()

tests/unit/test_email_helpers.py

@@ -0,0 +1,38 @@
+"""Tests for email helper functions in blueprints/email/helpers.py."""
+
+from blueprints.email.helpers import generate_email_token, get_user_email_address
+
+
+class TestGenerateEmailToken:
+    def test_returns_16_char_hex(self):
+        token = generate_email_token("user-123", "my-secret")
+        assert len(token) == 16
+        assert all(c in "0123456789abcdef" for c in token)
+
+    def test_deterministic(self):
+        t1 = generate_email_token("user-123", "my-secret")
+        t2 = generate_email_token("user-123", "my-secret")
+        assert t1 == t2
+
+    def test_different_users_different_tokens(self):
+        t1 = generate_email_token("user-1", "secret")
+        t2 = generate_email_token("user-2", "secret")
+        assert t1 != t2
+
+    def test_different_secrets_different_tokens(self):
+        t1 = generate_email_token("user-1", "secret-a")
+        t2 = generate_email_token("user-1", "secret-b")
+        assert t1 != t2
+
+
+class TestGetUserEmailAddress:
+    def test_formats_correctly(self):
+        addr = get_user_email_address("abc123", "example.com")
+        assert addr == "ask+abc123@example.com"
+
+    def test_preserves_token(self):
+        token = "deadbeef12345678"
+        addr = get_user_email_address(token, "mail.test.org")
+        assert token in addr
+        assert addr.startswith("ask+")
+        assert "@mail.test.org" in addr

tests/unit/test_obsidian_service.py

@@ -0,0 +1,259 @@
+"""Tests for ObsidianService markdown parsing and file operations."""
+
+import os
+from datetime import datetime
+from pathlib import Path
+from unittest.mock import patch
+
+import pytest
+
+# Set vault path before importing so __init__ validation passes
+_test_vault_dir = None
+
+
+@pytest.fixture(autouse=True)
+def vault_dir(tmp_path):
+    """Create a temporary vault directory with a sample .md file."""
+    global _test_vault_dir
+    _test_vault_dir = tmp_path
+
+    # Create a sample markdown file so vault validation passes
+    sample = tmp_path / "sample.md"
+    sample.write_text("# Sample\nHello world")
+
+    with patch.dict(os.environ, {"OBSIDIAN_VAULT_PATH": str(tmp_path)}):
+        yield tmp_path
+
+
+@pytest.fixture
+def service(vault_dir):
+    from utils.obsidian_service import ObsidianService
+
+    return ObsidianService()
+
+
+class TestParseMarkdown:
+    def test_extracts_frontmatter(self, service):
+        content = "---\ntitle: Test Note\ntags: [cat, vet]\n---\n\nBody content"
+        result = service.parse_markdown(content)
+        assert result["metadata"]["title"] == "Test Note"
+        assert result["metadata"]["tags"] == ["cat", "vet"]
+
+    def test_no_frontmatter(self, service):
+        content = "Just body content with no frontmatter"
+        result = service.parse_markdown(content)
+        assert result["metadata"] == {}
+        assert "Just body content" in result["content"]
+
+    def test_invalid_yaml_frontmatter(self, service):
+        content = "---\n: invalid: yaml: [[\n---\n\nBody"
+        result = service.parse_markdown(content)
+        assert result["metadata"] == {}
+
+    def test_extracts_tags(self, service):
+        content = "Some text with #tag1 and #tag2 here"
+        result = service.parse_markdown(content)
+        assert "tag1" in result["tags"]
+        assert "tag2" in result["tags"]
+
+    def test_extracts_wikilinks(self, service):
+        content = "Link to [[Other Note]] and [[Another Page]]"
+        result = service.parse_markdown(content)
+        assert "Other Note" in result["wikilinks"]
+        assert "Another Page" in result["wikilinks"]
+
+    def test_extracts_embeds(self, service):
+        content = "An embed [[!my_embed]] here"
+        result = service.parse_markdown(content)
+        assert "my_embed" in result["embeds"]
+
+    def test_cleans_wikilinks_from_content(self, service):
+        content = "Text with [[link]] included"
+        result = service.parse_markdown(content)
+        assert "[[" not in result["content"]
+        assert "]]" not in result["content"]
+
+    def test_filepath_passed_through(self, service):
+        result = service.parse_markdown("text", filepath=Path("/vault/note.md"))
+        assert result["filepath"] == "/vault/note.md"
+
+    def test_filepath_none_by_default(self, service):
+        result = service.parse_markdown("text")
+        assert result["filepath"] is None
+
+    def test_empty_content(self, service):
+        result = service.parse_markdown("")
+        assert result["metadata"] == {}
+        assert result["tags"] == []
+        assert result["wikilinks"] == []
+        assert result["embeds"] == []
+
+
+class TestGetDailyNotePath:
+    def test_formats_path_correctly(self, service):
+        date = datetime(2026, 3, 15)
+        path = service.get_daily_note_path(date)
+        assert path == "journal/2026/2026-03-15.md"
+
+    def test_defaults_to_today(self, service):
+        path = service.get_daily_note_path()
+        today = datetime.now()
+        assert today.strftime("%Y-%m-%d") in path
+        assert path.startswith(f"journal/{today.strftime('%Y')}/")
+
+
+class TestWalkVault:
+    def test_finds_markdown_files(self, service, vault_dir):
+        (vault_dir / "note1.md").write_text("# Note 1")
+        (vault_dir / "subdir").mkdir()
+        (vault_dir / "subdir" / "note2.md").write_text("# Note 2")
+
+        files = service.walk_vault()
+        filenames = [f.name for f in files]
+        assert "sample.md" in filenames
+        assert "note1.md" in filenames
+        assert "note2.md" in filenames
+
+    def test_excludes_obsidian_dir(self, service, vault_dir):
+        obsidian_dir = vault_dir / ".obsidian"
+        obsidian_dir.mkdir()
+        (obsidian_dir / "config.md").write_text("config")
+
+        files = service.walk_vault()
+        filenames = [f.name for f in files]
+        assert "config.md" not in filenames
+
+    def test_ignores_non_md_files(self, service, vault_dir):
+        (vault_dir / "image.png").write_bytes(b"\x89PNG")
+
+        files = service.walk_vault()
+        filenames = [f.name for f in files]
+        assert "image.png" not in filenames
+
+
+class TestCreateNote:
+    def test_creates_file(self, service, vault_dir):
+        path = service.create_note("My Test Note", "Body content")
+        full_path = vault_dir / path
+        assert full_path.exists()
+
+    def test_sanitizes_title(self, service, vault_dir):
+        path = service.create_note("Hello World! @#$", "Body")
+        assert "hello-world" in path
+        assert "@" not in path
+        assert "#" not in path
+
+    def test_includes_frontmatter(self, service, vault_dir):
+        path = service.create_note("Test", "Body", tags=["cat", "vet"])
+        full_path = vault_dir / path
+        content = full_path.read_text()
+        assert "---" in content
+        assert "created_by: simbarag" in content
+        assert "cat" in content
+        assert "vet" in content
+
+    def test_custom_folder(self, service, vault_dir):
+        path = service.create_note("Test", "Body", folder="custom/subfolder")
+        assert path.startswith("custom/subfolder/")
+        assert (vault_dir / path).exists()
+
+
+class TestDailyNoteTasks:
+    def test_get_tasks_from_daily_note(self, service, vault_dir):
+        # Create a daily note with tasks
+        date = datetime(2026, 1, 15)
+        rel_path = service.get_daily_note_path(date)
+        note_path = vault_dir / rel_path
+        note_path.parent.mkdir(parents=True, exist_ok=True)
+        note_path.write_text(
+            "---\nmodified: 2026-01-15\n---\n"
+            "### tasks\n\n"
+            "- [ ] Feed the cat\n"
+            "- [x] Clean litter box\n"
+            "- [ ] Buy cat food\n\n"
+            "### log\n"
+        )
+
+        result = service.get_daily_tasks(date)
+        assert result["found"] is True
+        assert len(result["tasks"]) == 3
+        assert result["tasks"][0] == {"text": "Feed the cat", "done": False}
+        assert result["tasks"][1] == {"text": "Clean litter box", "done": True}
+        assert result["tasks"][2] == {"text": "Buy cat food", "done": False}
+
+    def test_get_tasks_no_note(self, service):
+        date = datetime(2099, 12, 31)
+        result = service.get_daily_tasks(date)
+        assert result["found"] is False
+        assert result["tasks"] == []
+
+    def test_add_task_creates_note(self, service, vault_dir):
+        date = datetime(2026, 6, 1)
+        result = service.add_task_to_daily_note("Walk the cat", date)
+        assert result["success"] is True
+        assert result["created_note"] is True
+
+        # Verify file was created with the task
+        note_path = vault_dir / result["path"]
+        content = note_path.read_text()
+        assert "- [ ] Walk the cat" in content
+
+    def test_add_task_to_existing_note(self, service, vault_dir):
+        date = datetime(2026, 6, 2)
+        rel_path = service.get_daily_note_path(date)
+        note_path = vault_dir / rel_path
+        note_path.parent.mkdir(parents=True, exist_ok=True)
+        note_path.write_text(
+            "---\nmodified: 2026-06-02\n---\n"
+            "### tasks\n\n"
+            "- [ ] Existing task\n\n"
+            "### log\n"
+        )
+
+        result = service.add_task_to_daily_note("New task", date)
+        assert result["success"] is True
+        assert result["created_note"] is False
+
+        content = note_path.read_text()
+        assert "- [ ] Existing task" in content
+        assert "- [ ] New task" in content
+
+    def test_complete_task_exact_match(self, service, vault_dir):
+        date = datetime(2026, 6, 3)
+        rel_path = service.get_daily_note_path(date)
+        note_path = vault_dir / rel_path
+        note_path.parent.mkdir(parents=True, exist_ok=True)
+        note_path.write_text("### tasks\n\n" "- [ ] Feed the cat\n" "- [ ] Buy food\n")
+
+        result = service.complete_task_in_daily_note("Feed the cat", date)
+        assert result["success"] is True
+
+        content = note_path.read_text()
+        assert "- [x] Feed the cat" in content
+        assert "- [ ] Buy food" in content  # Other task unchanged
+
+    def test_complete_task_partial_match(self, service, vault_dir):
+        date = datetime(2026, 6, 4)
+        rel_path = service.get_daily_note_path(date)
+        note_path = vault_dir / rel_path
+        note_path.parent.mkdir(parents=True, exist_ok=True)
+        note_path.write_text("### tasks\n\n- [ ] Feed the cat at 5pm\n")
+
+        result = service.complete_task_in_daily_note("Feed the cat", date)
+        assert result["success"] is True
+
+    def test_complete_task_not_found(self, service, vault_dir):
+        date = datetime(2026, 6, 5)
+        rel_path = service.get_daily_note_path(date)
+        note_path = vault_dir / rel_path
+        note_path.parent.mkdir(parents=True, exist_ok=True)
+        note_path.write_text("### tasks\n\n- [ ] Feed the cat\n")
+
+        result = service.complete_task_in_daily_note("Walk the dog", date)
+        assert result["success"] is False
+        assert "not found" in result["error"]
+
+    def test_complete_task_no_note(self, service):
+        date = datetime(2099, 12, 31)
+        result = service.complete_task_in_daily_note("Something", date)
+        assert result["success"] is False

tests/unit/test_rate_limiting.py

@@ -0,0 +1,92 @@
+"""Tests for rate limiting logic in email and WhatsApp blueprints."""
+
+import time
+
+
+class TestEmailRateLimit:
+    def setup_method(self):
+        """Reset rate limit store before each test."""
+        from blueprints.email import _rate_limit_store
+
+        _rate_limit_store.clear()
+
+    def test_allows_under_limit(self):
+        from blueprints.email import _check_rate_limit, RATE_LIMIT_MAX
+
+        for _ in range(RATE_LIMIT_MAX):
+            assert _check_rate_limit("sender@test.com") is True
+
+    def test_blocks_at_limit(self):
+        from blueprints.email import _check_rate_limit, RATE_LIMIT_MAX
+
+        for _ in range(RATE_LIMIT_MAX):
+            _check_rate_limit("sender@test.com")
+
+        assert _check_rate_limit("sender@test.com") is False
+
+    def test_different_senders_independent(self):
+        from blueprints.email import _check_rate_limit, RATE_LIMIT_MAX
+
+        for _ in range(RATE_LIMIT_MAX):
+            _check_rate_limit("user1@test.com")
+
+        # user1 is at limit, but user2 should be fine
+        assert _check_rate_limit("user1@test.com") is False
+        assert _check_rate_limit("user2@test.com") is True
+
+    def test_window_expiry(self):
+        from blueprints.email import (
+            _check_rate_limit,
+            _rate_limit_store,
+            RATE_LIMIT_MAX,
+        )
+
+        # Fill up the rate limit with timestamps in the past
+        past = time.monotonic() - 999  # Well beyond any window
+        _rate_limit_store["old@test.com"] = [past] * RATE_LIMIT_MAX
+
+        # Should be allowed because all timestamps are expired
+        assert _check_rate_limit("old@test.com") is True
+
+
+class TestWhatsAppRateLimit:
+    def setup_method(self):
+        """Reset rate limit store before each test."""
+        from blueprints.whatsapp import _rate_limit_store
+
+        _rate_limit_store.clear()
+
+    def test_allows_under_limit(self):
+        from blueprints.whatsapp import _check_rate_limit, RATE_LIMIT_MAX
+
+        for _ in range(RATE_LIMIT_MAX):
+            assert _check_rate_limit("whatsapp:+1234567890") is True
+
+    def test_blocks_at_limit(self):
+        from blueprints.whatsapp import _check_rate_limit, RATE_LIMIT_MAX
+
+        for _ in range(RATE_LIMIT_MAX):
+            _check_rate_limit("whatsapp:+1234567890")
+
+        assert _check_rate_limit("whatsapp:+1234567890") is False
+
+    def test_different_numbers_independent(self):
+        from blueprints.whatsapp import _check_rate_limit, RATE_LIMIT_MAX
+
+        for _ in range(RATE_LIMIT_MAX):
+            _check_rate_limit("whatsapp:+1111111111")
+
+        assert _check_rate_limit("whatsapp:+1111111111") is False
+        assert _check_rate_limit("whatsapp:+2222222222") is True
+
+    def test_window_expiry(self):
+        from blueprints.whatsapp import (
+            _check_rate_limit,
+            _rate_limit_store,
+            RATE_LIMIT_MAX,
+        )
+
+        past = time.monotonic() - 999
+        _rate_limit_store["whatsapp:+9999999999"] = [past] * RATE_LIMIT_MAX
+
+        assert _check_rate_limit("whatsapp:+9999999999") is True

tests/unit/test_user_model.py

@@ -0,0 +1,86 @@
+"""Tests for User model methods in blueprints/users/models.py."""
+
+from unittest.mock import MagicMock
+
+import bcrypt
+
+
+class TestUserModelMethods:
+    """Test User model methods without requiring a database connection.
+
+    We instantiate a mock object with the same methods as User
+    to avoid Tortoise ORM initialization.
+    """
+
+    def _make_user(self, ldap_groups=None, password=None):
+        """Create a mock user with real method implementations."""
+        from blueprints.users.models import User
+
+        user = MagicMock(spec=User)
+        user.ldap_groups = ldap_groups
+        user.password = password
+
+        # Bind real methods
+        user.has_group = lambda group: group in (user.ldap_groups or [])
+        user.is_admin = lambda: user.has_group("lldap_admin")
+
+        def set_password(plain):
+            user.password = bcrypt.hashpw(plain.encode("utf-8"), bcrypt.gensalt())
+
+        user.set_password = set_password
+
+        def verify_password(plain):
+            if not user.password:
+                return False
+            return bcrypt.checkpw(plain.encode("utf-8"), user.password)
+
+        user.verify_password = verify_password
+
+        return user
+
+    def test_has_group_true(self):
+        user = self._make_user(ldap_groups=["lldap_admin", "users"])
+        assert user.has_group("lldap_admin") is True
+        assert user.has_group("users") is True
+
+    def test_has_group_false(self):
+        user = self._make_user(ldap_groups=["users"])
+        assert user.has_group("lldap_admin") is False
+
+    def test_has_group_empty_list(self):
+        user = self._make_user(ldap_groups=[])
+        assert user.has_group("anything") is False
+
+    def test_has_group_none(self):
+        user = self._make_user(ldap_groups=None)
+        assert user.has_group("anything") is False
+
+    def test_is_admin_true(self):
+        user = self._make_user(ldap_groups=["lldap_admin"])
+        assert user.is_admin() is True
+
+    def test_is_admin_false(self):
+        user = self._make_user(ldap_groups=["users"])
+        assert user.is_admin() is False
+
+    def test_is_admin_empty(self):
+        user = self._make_user(ldap_groups=[])
+        assert user.is_admin() is False
+
+    def test_set_and_verify_password(self):
+        user = self._make_user()
+        user.set_password("hunter2")
+        assert user.password is not None
+        assert user.verify_password("hunter2") is True
+        assert user.verify_password("wrong") is False
+
+    def test_verify_password_no_password_set(self):
+        user = self._make_user(password=None)
+        assert user.verify_password("anything") is False
+
+    def test_password_is_hashed(self):
+        user = self._make_user()
+        user.set_password("mypassword")
+        # The stored password should not be the plaintext
+        assert user.password != b"mypassword"
+        assert user.password != "mypassword"

tests/unit/test_ynab_service.py

@@ -0,0 +1,254 @@
+"""Tests for YNAB service data formatting and filtering logic."""
+
+import os
+from unittest.mock import MagicMock, patch
+
+import pytest
+
+
+def _mock_category(
+    name, budgeted, activity, balance, deleted=False, hidden=False, goal_type=None
+):
+    cat = MagicMock()
+    cat.name = name
+    cat.budgeted = budgeted
+    cat.activity = activity
+    cat.balance = balance
+    cat.deleted = deleted
+    cat.hidden = hidden
+    cat.goal_type = goal_type
+    return cat
+
+
+def _mock_transaction(
+    var_date, payee_name, category_name, amount, memo="", deleted=False, approved=True
+):
+    txn = MagicMock()
+    txn.var_date = var_date
+    txn.payee_name = payee_name
+    txn.category_name = category_name
+    txn.amount = amount
+    txn.memo = memo
+    txn.deleted = deleted
+    txn.approved = approved
+    return txn
+
+
+@pytest.fixture
+def ynab_service():
+    """Create a YNABService with mocked API client."""
+    with patch.dict(
+        os.environ, {"YNAB_ACCESS_TOKEN": "fake-token", "YNAB_BUDGET_ID": "test-budget"}
+    ):
+        with patch("utils.ynab_service.ynab") as mock_ynab:
+            # Mock the configuration and API client chain
+            mock_ynab.Configuration.return_value = MagicMock()
+            mock_ynab.ApiClient.return_value = MagicMock()
+            mock_ynab.PlansApi.return_value = MagicMock()
+            mock_ynab.TransactionsApi.return_value = MagicMock()
+            mock_ynab.MonthsApi.return_value = MagicMock()
+            mock_ynab.CategoriesApi.return_value = MagicMock()
+
+            from utils.ynab_service import YNABService
+
+            service = YNABService()
+            yield service
+
+
+class TestGetBudgetSummary:
+    def test_calculates_totals(self, ynab_service):
+        categories = [
+            _mock_category("Groceries", 500_000, -350_000, 150_000),
+            _mock_category("Rent", 1_500_000, -1_500_000, 0),
+        ]
+
+        mock_month = MagicMock()
+        mock_month.to_be_budgeted = 200_000
+
+        mock_budget = MagicMock()
+        mock_budget.name = "My Budget"
+        mock_budget.months = [mock_month]
+        mock_budget.categories = categories
+        mock_budget.currency_format = MagicMock(iso_code="USD")
+
+        mock_response = MagicMock()
+        mock_response.data.budget = mock_budget
+        ynab_service.plans_api.get_plan_by_id.return_value = mock_response
+
+        result = ynab_service.get_budget_summary()
+
+        assert result["budget_name"] == "My Budget"
+        assert result["to_be_budgeted"] == 200.0
+        assert result["total_budgeted"] == 2000.0  # (500k + 1500k) / 1000
+        assert result["total_activity"] == -1850.0
+        assert result["currency_format"] == "USD"
+
+    def test_skips_deleted_and_hidden(self, ynab_service):
+        categories = [
+            _mock_category("Active", 100_000, -50_000, 50_000),
+            _mock_category("Deleted", 999_000, -999_000, 0, deleted=True),
+            _mock_category("Hidden", 999_000, -999_000, 0, hidden=True),
+        ]
+
+        mock_month = MagicMock()
+        mock_month.to_be_budgeted = 0
+        mock_budget = MagicMock()
+        mock_budget.name = "Budget"
+        mock_budget.months = [mock_month]
+        mock_budget.categories = categories
+        mock_budget.currency_format = None
+
+        mock_response = MagicMock()
+        mock_response.data.budget = mock_budget
+        ynab_service.plans_api.get_plan_by_id.return_value = mock_response
+
+        result = ynab_service.get_budget_summary()
+        assert result["total_budgeted"] == 100.0
+        assert result["currency_format"] == "USD"  # Default fallback
+
+
+class TestGetTransactions:
+    def test_filters_by_date_range(self, ynab_service):
+        transactions = [
+            _mock_transaction("2026-01-05", "Store", "Groceries", -25_000),
+            _mock_transaction("2026-01-15", "Gas", "Transport", -40_000),
+            _mock_transaction(
+                "2026-02-01", "Store", "Groceries", -30_000
+            ),  # Out of range
+        ]
+
+        mock_response = MagicMock()
+        mock_response.data.transactions = transactions
+        ynab_service.transactions_api.get_transactions.return_value = mock_response
+
+        result = ynab_service.get_transactions(
+            start_date="2026-01-01", end_date="2026-01-31"
+        )
+
+        assert result["count"] == 2
+        assert result["total_amount"] == -65.0
+
+    def test_filters_by_category(self, ynab_service):
+        transactions = [
+            _mock_transaction("2026-01-05", "Store", "Groceries", -25_000),
+            _mock_transaction("2026-01-06", "Gas", "Transport", -40_000),
+        ]
+
+        mock_response = MagicMock()
+        mock_response.data.transactions = transactions
+        ynab_service.transactions_api.get_transactions.return_value = mock_response
+
+        result = ynab_service.get_transactions(
+            start_date="2026-01-01",
+            end_date="2026-01-31",
+            category_name="groceries",  # Case insensitive
+        )
+
+        assert result["count"] == 1
+        assert result["transactions"][0]["category"] == "Groceries"
+
+    def test_filters_by_payee(self, ynab_service):
+        transactions = [
+            _mock_transaction("2026-01-05", "Whole Foods", "Groceries", -25_000),
+            _mock_transaction("2026-01-06", "Shell Gas", "Transport", -40_000),
+        ]
+
+        mock_response = MagicMock()
+        mock_response.data.transactions = transactions
+        ynab_service.transactions_api.get_transactions.return_value = mock_response
+
+        result = ynab_service.get_transactions(
+            start_date="2026-01-01",
+            end_date="2026-01-31",
+            payee_name="whole",
+        )
+
+        assert result["count"] == 1
+        assert result["transactions"][0]["payee"] == "Whole Foods"
+
+    def test_skips_deleted(self, ynab_service):
+        transactions = [
+            _mock_transaction("2026-01-05", "Store", "Groceries", -25_000),
+            _mock_transaction("2026-01-06", "Deleted", "Other", -10_000, deleted=True),
+        ]
+
+        mock_response = MagicMock()
+        mock_response.data.transactions = transactions
+        ynab_service.transactions_api.get_transactions.return_value = mock_response
+
+        result = ynab_service.get_transactions(
+            start_date="2026-01-01", end_date="2026-01-31"
+        )
+
+        assert result["count"] == 1
+
+    def test_converts_milliunits(self, ynab_service):
+        transactions = [
+            _mock_transaction("2026-01-05", "Store", "Groceries", -12_340),
+        ]
+
+        mock_response = MagicMock()
+        mock_response.data.transactions = transactions
+        ynab_service.transactions_api.get_transactions.return_value = mock_response
+
+        result = ynab_service.get_transactions(
+            start_date="2026-01-01", end_date="2026-01-31"
+        )
+
+        assert result["transactions"][0]["amount"] == -12.34
+
+    def test_sorts_by_date_descending(self, ynab_service):
+        transactions = [
+            _mock_transaction("2026-01-01", "A", "Cat", -10_000),
+            _mock_transaction("2026-01-15", "B", "Cat", -20_000),
+            _mock_transaction("2026-01-10", "C", "Cat", -30_000),
+        ]
+
+        mock_response = MagicMock()
+        mock_response.data.transactions = transactions
+        ynab_service.transactions_api.get_transactions.return_value = mock_response
+
+        result = ynab_service.get_transactions(
+            start_date="2026-01-01", end_date="2026-01-31"
+        )
+
+        dates = [t["date"] for t in result["transactions"]]
+        assert dates == sorted(dates, reverse=True)
+
+
+class TestGetCategorySpending:
+    def test_month_format_normalization(self, ynab_service):
+        """Passing YYYY-MM should be normalized to YYYY-MM-01."""
+        categories = [_mock_category("Food", 100_000, -50_000, 50_000)]
+
+        mock_month = MagicMock()
+        mock_month.categories = categories
+        mock_month.to_be_budgeted = 0
+
+        mock_response = MagicMock()
+        mock_response.data.month = mock_month
+        ynab_service.months_api.get_plan_month.return_value = mock_response
+
+        result = ynab_service.get_category_spending("2026-03")
+
+        assert result["month"] == "2026-03"
+
+    def test_identifies_overspent(self, ynab_service):
+        categories = [
+            _mock_category("Dining", 200_000, -300_000, -100_000),  # Overspent
+            _mock_category("Groceries", 500_000, -400_000, 100_000),  # Fine
+        ]
+
+        mock_month = MagicMock()
+        mock_month.categories = categories
+        mock_month.to_be_budgeted = 0
+
+        mock_response = MagicMock()
+        mock_response.data.month = mock_month
+        ynab_service.months_api.get_plan_month.return_value = mock_response
+
+        result = ynab_service.get_category_spending("2026-03")
+
+        assert len(result["overspent_categories"]) == 1
+        assert result["overspent_categories"][0]["name"] == "Dining"
+        assert result["overspent_categories"][0]["overspent_by"] == 100.0

utils/s3_client.py

@@ -47,6 +47,16 @@ async def get_image(key: str) -> tuple[bytes, str]:
     return body, content_type
 
 
+async def generate_presigned_url(key: str, expires_in: int = 3600) -> str:
+    async with _get_client() as client:
+        url = await client.generate_presigned_url(
+            "get_object",
+            Params={"Bucket": S3_BUCKET_NAME, "Key": key},
+            ExpiresIn=expires_in,
+        )
+    return url
+
+
 async def delete_image(key: str) -> None:
     async with _get_client() as client:
         await client.delete_object(Bucket=S3_BUCKET_NAME, Key=key)

uv.lock

@@ -17,6 +17,42 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/87/1a/956c6b1e35881bb9835a33c8db1565edcd133f8e45321010489092a0df40/aerich-0.9.2-py3-none-any.whl", hash = "sha256:d0f007acb21f6559f1eccd4e404fb039cf48af2689e0669afa62989389c0582d", size = 46451, upload-time = "2025-10-10T05:53:48.71Z" },
 ]
 
+[[package]]
+name = "aioboto3"
+version = "15.5.0"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "aiobotocore", extra = ["boto3"] },
+    { name = "aiofiles" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/a2/01/92e9ab00f36e2899315f49eefcd5b4685fbb19016c7f19a9edf06da80bb0/aioboto3-15.5.0.tar.gz", hash = "sha256:ea8d8787d315594842fbfcf2c4dce3bac2ad61be275bc8584b2ce9a3402a6979", size = 255069, upload-time = "2025-10-30T13:37:16.122Z" }
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+]
+
+[[package]]
+name = "aiobotocore"
+version = "2.25.1"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "aiohttp" },
+    { name = "aioitertools" },
+    { name = "botocore" },
+    { name = "jmespath" },
+    { name = "multidict" },
+    { name = "python-dateutil" },
+    { name = "wrapt" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/62/94/2e4ec48cf1abb89971cb2612d86f979a6240520f0a659b53a43116d344dc/aiobotocore-2.25.1.tar.gz", hash = "sha256:ea9be739bfd7ece8864f072ec99bb9ed5c7e78ebb2b0b15f29781fbe02daedbc", size = 120560, upload-time = "2025-10-28T22:33:21.787Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/95/2a/d275ec4ce5cd0096665043995a7d76f5d0524853c76a3d04656de49f8808/aiobotocore-2.25.1-py3-none-any.whl", hash = "sha256:eb6daebe3cbef5b39a0bb2a97cffbe9c7cb46b2fcc399ad141f369f3c2134b1f", size = 86039, upload-time = "2025-10-28T22:33:19.949Z" },
+]
+
+[package.optional-dependencies]
+boto3 = [
+    { name = "boto3" },
+]
+
 [[package]]
 name = "aiofiles"
 version = "25.1.0"
@@ -115,6 +151,24 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/1a/99/84ba7273339d0f3dfa57901b846489d2e5c2cd731470167757f1935fffbd/aiohttp_retry-2.9.1-py3-none-any.whl", hash = "sha256:66d2759d1921838256a05a3f80ad7e724936f083e35be5abb5e16eed6be6dc54", size = 9981, upload-time = "2024-11-06T10:44:52.917Z" },
 ]
 
+[[package]]
+name = "aioimaplib"
+version = "2.0.1"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/ee/da/a454c47fb8522e607425e15bf1f49ccfdb3d75f4071f40b63ebd49573495/aioimaplib-2.0.1.tar.gz", hash = "sha256:5a494c3b75f220977048f5eb2c7ba9c0570a3148aaf38bee844e37e4d7af8648", size = 35555, upload-time = "2025-01-16T10:38:23.14Z" }
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+]
+
+[[package]]
+name = "aioitertools"
+version = "0.13.0"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/fd/3c/53c4a17a05fb9ea2313ee1777ff53f5e001aefd5cc85aa2f4c2d982e1e38/aioitertools-0.13.0.tar.gz", hash = "sha256:620bd241acc0bbb9ec819f1ab215866871b4bbd1f73836a55f799200ee86950c", size = 19322, upload-time = "2025-11-06T22:17:07.609Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/10/a1/510b0a7fadc6f43a6ce50152e69dbd86415240835868bb0bd9b5b88b1e06/aioitertools-0.13.0-py3-none-any.whl", hash = "sha256:0be0292b856f08dfac90e31f4739432f4cb6d7520ab9eb73e143f4f2fa5259be", size = 24182, upload-time = "2025-11-06T22:17:06.502Z" },
+]
+
 [[package]]
 name = "aiosignal"
 version = "1.4.0"
@@ -331,6 +385,34 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/10/cb/f2ad4230dc2eb1a74edf38f1a38b9b52277f75bef262d8908e60d957e13c/blinker-1.9.0-py3-none-any.whl", hash = "sha256:ba0efaa9080b619ff2f3459d1d500c57bddea4a6b424b60a91141db6fd2f08bc", size = 8458, upload-time = "2024-11-08T17:25:46.184Z" },
 ]
 
+[[package]]
+name = "boto3"
+version = "1.40.61"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "botocore" },
+    { name = "jmespath" },
+    { name = "s3transfer" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/ed/f9/6ef8feb52c3cce5ec3967a535a6114b57ac7949fd166b0f3090c2b06e4e5/boto3-1.40.61.tar.gz", hash = "sha256:d6c56277251adf6c2bdd25249feae625abe4966831676689ff23b4694dea5b12", size = 111535, upload-time = "2025-10-28T19:26:57.247Z" }
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+]
+
+[[package]]
+name = "botocore"
+version = "1.40.61"
+source = { registry = "https://pypi.org/simple" }
+dependencies = [
+    { name = "jmespath" },
+    { name = "python-dateutil" },
+    { name = "urllib3" },
+]
+sdist = { url = "https://files.pythonhosted.org/packages/28/a3/81d3a47c2dbfd76f185d3b894f2ad01a75096c006a2dd91f237dca182188/botocore-1.40.61.tar.gz", hash = "sha256:a2487ad69b090f9cccd64cf07c7021cd80ee9c0655ad974f87045b02f3ef52cd", size = 14393956, upload-time = "2025-10-28T19:26:46.108Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/38/c5/f6ce561004db45f0b847c2cd9b19c67c6bf348a82018a48cb718be6b58b0/botocore-1.40.61-py3-none-any.whl", hash = "sha256:17ebae412692fd4824f99cde0f08d50126dc97954008e5ba2b522eb049238aa7", size = 14055973, upload-time = "2025-10-28T19:26:42.15Z" },
+]
+
 [[package]]
 name = "build"
 version = "1.3.0"
@@ -523,6 +605,75 @@ wheels = [
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+[[package]]
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+version = "7.13.5"
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