diff --git a/packages/server/pyproject.toml b/packages/server/pyproject.toml
index 0c32927..ce44658 100644
--- a/packages/server/pyproject.toml
+++ b/packages/server/pyproject.toml
@@ -18,6 +18,7 @@ dependencies = [
     "apscheduler>=3.10,<4",
     "jinja2>=3.1",
     "aiohttp>=3.9",
+    "anthropic>=0.42",
 ]
 
 [project.optional-dependencies]
diff --git a/packages/server/src/immich_watcher_server/ai/__init__.py b/packages/server/src/immich_watcher_server/ai/__init__.py
new file mode 100644
index 0000000..68ae4fe
--- /dev/null
+++ b/packages/server/src/immich_watcher_server/ai/__init__.py
@@ -0,0 +1 @@
+"""Claude AI integration for intelligent notifications and conversational bot."""
diff --git a/packages/server/src/immich_watcher_server/ai/service.py b/packages/server/src/immich_watcher_server/ai/service.py
new file mode 100644
index 0000000..61110fc
--- /dev/null
+++ b/packages/server/src/immich_watcher_server/ai/service.py
@@ -0,0 +1,220 @@
+"""Claude AI service for generating intelligent responses and captions."""
+
+from __future__ import annotations
+
+import logging
+from typing import Any
+
+from ..config import settings
+
+_LOGGER = logging.getLogger(__name__)
+
+# Per-chat conversation history (in-memory, capped)
+_conversations: dict[str, list[dict[str, str]]] = {}
+_MAX_HISTORY = 20
+
+SYSTEM_PROMPT = """You are an assistant for Immich Watcher, a photo album notification service connected to an Immich photo server. You help users understand their photo albums, recent changes, and manage their notification preferences.
+
+You have access to the following tools to interact with the system. Use them when the user asks about their albums, wants to manage trackers, or needs information.
+
+Be concise, friendly, and helpful. When describing photos, focus on the people, places, and moments captured. Use the user's language (detect from their message).
+
+Context about the current setup will be provided with each message."""
+
+
+def is_ai_enabled() -> bool:
+    """Check if AI features are available."""
+    return bool(settings.anthropic_api_key)
+
+
+def _get_client():
+    """Get the Anthropic async client (lazy import)."""
+    from anthropic import AsyncAnthropic
+    return AsyncAnthropic(api_key=settings.anthropic_api_key)
+
+
+def _get_conversation(chat_id: str) -> list[dict[str, str]]:
+    """Get or create conversation history for a chat."""
+    if chat_id not in _conversations:
+        _conversations[chat_id] = []
+    return _conversations[chat_id]
+
+
+def _trim_conversation(chat_id: str) -> None:
+    """Keep conversation history within limits."""
+    conv = _conversations.get(chat_id, [])
+    if len(conv) > _MAX_HISTORY:
+        _conversations[chat_id] = conv[-_MAX_HISTORY:]
+
+
+async def chat(
+    chat_id: str,
+    user_message: str,
+    context: str = "",
+    tools: list[dict] | None = None,
+) -> str:
+    """Send a message to Claude and get a response.
+
+    Args:
+        chat_id: Telegram chat ID (for conversation history)
+        user_message: The user's message
+        context: Additional context about albums, trackers, etc.
+        tools: Optional tool definitions for function calling
+
+    Returns:
+        Claude's response text
+    """
+    if not is_ai_enabled():
+        return "AI features are not configured. Set IMMICH_WATCHER_ANTHROPIC_API_KEY to enable."
+
+    client = _get_client()
+    conversation = _get_conversation(chat_id)
+
+    # Add user message to history
+    conversation.append({"role": "user", "content": user_message})
+
+    # Build system prompt with context
+    system = SYSTEM_PROMPT
+    if context:
+        system += f"\n\nCurrent context:\n{context}"
+
+    try:
+        kwargs: dict[str, Any] = {
+            "model": settings.ai_model,
+            "max_tokens": settings.ai_max_tokens,
+            "system": system,
+            "messages": conversation,
+        }
+        if tools:
+            kwargs["tools"] = tools
+
+        response = await client.messages.create(**kwargs)
+
+        # Extract text response
+        text_parts = [
+            block.text for block in response.content if block.type == "text"
+        ]
+        assistant_message = "\n".join(text_parts) if text_parts else "I couldn't generate a response."
+
+        # Handle tool use if needed
+        tool_uses = [
+            block for block in response.content if block.type == "tool_use"
+        ]
+        if tool_uses and response.stop_reason == "tool_use":
+            # Return tool calls for the caller to handle
+            assistant_message += "\n[Tool calls pending - handled by webhook]"
+
+        # Add assistant response to history
+        conversation.append({"role": "assistant", "content": assistant_message})
+        _trim_conversation(chat_id)
+
+        return assistant_message
+
+    except Exception as err:
+        _LOGGER.error("Claude API error: %s", err)
+        return f"Sorry, I encountered an error: {type(err).__name__}"
+
+
+async def generate_caption(
+    event_data: dict[str, Any],
+    style: str = "friendly",
+) -> str | None:
+    """Generate an AI-powered notification caption for an album change event.
+
+    Args:
+        event_data: Album change event data (album_name, added_count, people, etc.)
+        style: Caption style - "friendly", "brief", or "detailed"
+
+    Returns:
+        Generated caption text, or None if AI is not available
+    """
+    if not is_ai_enabled():
+        return None
+
+    client = _get_client()
+
+    album_name = event_data.get("album_name", "Unknown")
+    added_count = event_data.get("added_count", 0)
+    removed_count = event_data.get("removed_count", 0)
+    change_type = event_data.get("change_type", "changed")
+    people = event_data.get("people", [])
+    assets = event_data.get("added_assets", [])
+
+    # Build a concise description for Claude
+    asset_summary = ""
+    for asset in assets[:5]:  # Limit to first 5 for context
+        name = asset.get("filename", "")
+        location = asset.get("city", "")
+        if location:
+            location = f" in {location}"
+        asset_summary += f"  - {name}{location}\n"
+
+    prompt = f"""Generate a {style} notification caption for this album change:
+
+Album: "{album_name}"
+Change: {change_type} ({added_count} added, {removed_count} removed)
+People detected: {', '.join(people) if people else 'none'}
+{f'Sample files:\\n{asset_summary}' if asset_summary else ''}
+
+Write a single notification message (1-3 sentences). No markdown, no hashtags. Match the language if album name suggests one."""
+
+    try:
+        response = await client.messages.create(
+            model=settings.ai_model,
+            max_tokens=256,
+            messages=[{"role": "user", "content": prompt}],
+        )
+        text_parts = [b.text for b in response.content if b.type == "text"]
+        return text_parts[0].strip() if text_parts else None
+    except Exception as err:
+        _LOGGER.error("AI caption generation failed: %s", err)
+        return None
+
+
+async def summarize_albums(
+    albums_data: list[dict[str, Any]],
+    recent_events: list[dict[str, Any]],
+) -> str:
+    """Generate a natural language summary of album activity.
+
+    Args:
+        albums_data: List of album info dicts
+        recent_events: Recent event log entries
+
+    Returns:
+        Human-friendly summary text
+    """
+    if not is_ai_enabled():
+        return "AI features are not configured."
+
+    client = _get_client()
+
+    events_text = ""
+    for event in recent_events[:10]:
+        events_text += f"  - {event.get('event_type')}: {event.get('album_name')} ({event.get('created_at', '')})\n"
+
+    albums_text = ""
+    for album in albums_data[:10]:
+        albums_text += f"  - {album.get('albumName', 'Unknown')} ({album.get('assetCount', 0)} assets)\n"
+
+    prompt = f"""Summarize this photo album activity concisely:
+
+Tracked albums:
+{albums_text or '  (none)'}
+
+Recent events:
+{events_text or '  (none)'}
+
+Write 2-4 sentences summarizing what's happening. Be conversational."""
+
+    try:
+        response = await client.messages.create(
+            model=settings.ai_model,
+            max_tokens=512,
+            messages=[{"role": "user", "content": prompt}],
+        )
+        text_parts = [b.text for b in response.content if b.type == "text"]
+        return text_parts[0].strip() if text_parts else "No summary available."
+    except Exception as err:
+        _LOGGER.error("AI summary generation failed: %s", err)
+        return f"Summary generation failed: {type(err).__name__}"
diff --git a/packages/server/src/immich_watcher_server/ai/telegram_webhook.py b/packages/server/src/immich_watcher_server/ai/telegram_webhook.py
new file mode 100644
index 0000000..cd73171
--- /dev/null
+++ b/packages/server/src/immich_watcher_server/ai/telegram_webhook.py
@@ -0,0 +1,190 @@
+"""Telegram webhook handler for AI bot interactions."""
+
+from __future__ import annotations
+
+import logging
+from typing import Any
+
+import aiohttp
+from fastapi import APIRouter, Depends, Request
+from sqlmodel import select
+from sqlmodel.ext.asyncio.session import AsyncSession
+
+from immich_watcher_core.telegram.media import TELEGRAM_API_BASE_URL
+
+from ..database.engine import get_session
+from ..database.models import AlbumTracker, EventLog, ImmichServer, NotificationTarget
+from .service import chat, is_ai_enabled, summarize_albums
+
+_LOGGER = logging.getLogger(__name__)
+
+router = APIRouter(prefix="/api/telegram", tags=["telegram-ai"])
+
+
+@router.post("/webhook/{bot_token}")
+async def telegram_webhook(
+    bot_token: str,
+    request: Request,
+    session: AsyncSession = Depends(get_session),
+):
+    """Handle incoming Telegram messages for AI bot.
+
+    This endpoint is registered with Telegram via setWebhook.
+    """
+    if not is_ai_enabled():
+        return {"ok": True, "skipped": "ai_disabled"}
+
+    try:
+        update = await request.json()
+    except Exception:
+        return {"ok": True, "error": "invalid_json"}
+
+    message = update.get("message")
+    if not message:
+        return {"ok": True, "skipped": "no_message"}
+
+    chat_info = message.get("chat", {})
+    chat_id = str(chat_info.get("id", ""))
+    text = message.get("text", "")
+
+    if not chat_id or not text:
+        return {"ok": True, "skipped": "empty"}
+
+    # Skip bot commands that aren't for us
+    if text.startswith("/start"):
+        await _send_reply(
+            bot_token, chat_id,
+            "Hi! I'm your Immich Watcher AI assistant. Ask me about your photo albums, "
+            "recent changes, or say 'summary' to get an overview."
+        )
+        return {"ok": True}
+
+    # Build context from database
+    context = await _build_context(session, chat_id)
+
+    # Handle special commands
+    if text.lower().strip() in ("summary", "what's new", "what's new?", "status"):
+        albums_data, recent_events = await _get_summary_data(session)
+        summary = await summarize_albums(albums_data, recent_events)
+        await _send_reply(bot_token, chat_id, summary)
+        return {"ok": True}
+
+    # General conversation with Claude
+    response = await chat(chat_id, text, context=context)
+    await _send_reply(bot_token, chat_id, response)
+    return {"ok": True}
+
+
+@router.post("/register-webhook")
+async def register_webhook(
+    request: Request,
+):
+    """Register webhook URL with Telegram Bot API.
+
+    Body: {"bot_token": "...", "webhook_url": "https://your-server/api/telegram/webhook/{token}"}
+    """
+    body = await request.json()
+    bot_token = body.get("bot_token")
+    webhook_url = body.get("webhook_url")
+
+    if not bot_token or not webhook_url:
+        return {"success": False, "error": "bot_token and webhook_url required"}
+
+    async with aiohttp.ClientSession() as http_session:
+        url = f"{TELEGRAM_API_BASE_URL}{bot_token}/setWebhook"
+        async with http_session.post(url, json={"url": webhook_url}) as resp:
+            result = await resp.json()
+            if result.get("ok"):
+                _LOGGER.info("Telegram webhook registered: %s", webhook_url)
+                return {"success": True}
+            return {"success": False, "error": result.get("description")}
+
+
+@router.post("/unregister-webhook")
+async def unregister_webhook(request: Request):
+    """Remove webhook from Telegram Bot API."""
+    body = await request.json()
+    bot_token = body.get("bot_token")
+
+    if not bot_token:
+        return {"success": False, "error": "bot_token required"}
+
+    async with aiohttp.ClientSession() as http_session:
+        url = f"{TELEGRAM_API_BASE_URL}{bot_token}/deleteWebhook"
+        async with http_session.post(url) as resp:
+            result = await resp.json()
+            return {"success": result.get("ok", False)}
+
+
+async def _send_reply(bot_token: str, chat_id: str, text: str) -> None:
+    """Send a text reply via Telegram Bot API."""
+    async with aiohttp.ClientSession() as http_session:
+        url = f"{TELEGRAM_API_BASE_URL}{bot_token}/sendMessage"
+        payload = {"chat_id": chat_id, "text": text, "parse_mode": "Markdown"}
+        try:
+            async with http_session.post(url, json=payload) as resp:
+                if resp.status != 200:
+                    result = await resp.json()
+                    _LOGGER.debug("Telegram reply failed: %s", result.get("description"))
+                    # Retry without parse_mode if Markdown fails
+                    if "parse" in str(result.get("description", "")).lower():
+                        payload["parse_mode"] = ""
+                        async with http_session.post(url, json=payload) as retry_resp:
+                            if retry_resp.status != 200:
+                                _LOGGER.warning("Telegram reply failed on retry")
+        except aiohttp.ClientError as err:
+            _LOGGER.error("Failed to send Telegram reply: %s", err)
+
+
+async def _build_context(session: AsyncSession, chat_id: str) -> str:
+    """Build context string from database for AI."""
+    parts = []
+
+    # Get all trackers
+    result = await session.exec(select(AlbumTracker).limit(10))
+    trackers = result.all()
+    if trackers:
+        parts.append(f"Active trackers: {len(trackers)}")
+        for t in trackers[:5]:
+            parts.append(f"  - {t.name}: {len(t.album_ids)} album(s), events: {', '.join(t.event_types)}")
+
+    # Get recent events
+    result = await session.exec(
+        select(EventLog).order_by(EventLog.created_at.desc()).limit(5)
+    )
+    events = result.all()
+    if events:
+        parts.append("Recent events:")
+        for e in events:
+            parts.append(f"  - {e.event_type}: {e.album_name} ({e.created_at.isoformat()[:16]})")
+
+    return "\n".join(parts) if parts else "No trackers or events configured yet."
+
+
+async def _get_summary_data(
+    session: AsyncSession,
+) -> tuple[list[dict[str, Any]], list[dict[str, Any]]]:
+    """Fetch data for album summary."""
+    # Get servers to fetch album lists
+    albums_data: list[dict[str, Any]] = []
+    servers_result = await session.exec(select(ImmichServer).limit(5))
+    for server in servers_result.all():
+        try:
+            from immich_watcher_core.immich_client import ImmichClient
+            async with aiohttp.ClientSession() as http_session:
+                client = ImmichClient(http_session, server.url, server.api_key)
+                albums = await client.get_albums()
+                albums_data.extend(albums[:20])
+        except Exception:
+            _LOGGER.debug("Failed to fetch albums from %s for summary", server.url)
+
+    # Get recent events
+    events_result = await session.exec(
+        select(EventLog).order_by(EventLog.created_at.desc()).limit(20)
+    )
+    recent_events = [
+        {"event_type": e.event_type, "album_name": e.album_name, "created_at": e.created_at.isoformat()}
+        for e in events_result.all()
+    ]
+
+    return albums_data, recent_events
diff --git a/packages/server/src/immich_watcher_server/config.py b/packages/server/src/immich_watcher_server/config.py
index dd3e2e9..467df4b 100644
--- a/packages/server/src/immich_watcher_server/config.py
+++ b/packages/server/src/immich_watcher_server/config.py
@@ -21,6 +21,11 @@ class Settings(BaseSettings):
     port: int = 8420
     debug: bool = False
 
+    # Claude AI (optional - leave empty to disable AI features)
+    anthropic_api_key: str = ""
+    ai_model: str = "claude-sonnet-4-20250514"
+    ai_max_tokens: int = 1024
+
     model_config = {"env_prefix": "IMMICH_WATCHER_"}
 
     @property
diff --git a/packages/server/src/immich_watcher_server/main.py b/packages/server/src/immich_watcher_server/main.py
index 8a1cef2..7df9a61 100644
--- a/packages/server/src/immich_watcher_server/main.py
+++ b/packages/server/src/immich_watcher_server/main.py
@@ -22,6 +22,7 @@ from .api.targets import router as targets_router
 from .api.users import router as users_router
 from .api.status import router as status_router
 from .api.sync import router as sync_router
+from .ai.telegram_webhook import router as telegram_ai_router
 
 logging.basicConfig(
     level=logging.DEBUG if settings.debug else logging.INFO,
@@ -71,6 +72,7 @@ app.include_router(targets_router)
 app.include_router(users_router)
 app.include_router(status_router)
 app.include_router(sync_router)
+app.include_router(telegram_ai_router)
 
 # Serve frontend static files if available
 _frontend_dist = Path(__file__).parent / "frontend"
@@ -81,7 +83,8 @@ if _frontend_dist.is_dir():
 @app.get("/api/health")
 async def health():
     """Health check endpoint."""
-    return {"status": "ok", "version": "0.1.0"}
+    from .ai.service import is_ai_enabled
+    return {"status": "ok", "version": "0.1.0", "ai_enabled": is_ai_enabled()}
 
 
 def run():
diff --git a/packages/server/src/immich_watcher_server/services/notifier.py b/packages/server/src/immich_watcher_server/services/notifier.py
index 2d43d54..9244d0d 100644
--- a/packages/server/src/immich_watcher_server/services/notifier.py
+++ b/packages/server/src/immich_watcher_server/services/notifier.py
@@ -33,6 +33,7 @@ async def send_notification(
     target: NotificationTarget,
     event_data: dict[str, Any],
     template: MessageTemplate | None = None,
+    use_ai_caption: bool = False,
 ) -> dict[str, Any]:
     """Send a notification to a target using event data.
 
@@ -40,13 +41,24 @@ async def send_notification(
         target: Notification destination (telegram or webhook)
         event_data: Album change event data (album_name, added_count, etc.)
         template: Optional message template (uses default if None)
+        use_ai_caption: If True, generate caption with Claude AI instead of template
     """
-    template_body = template.body if template else DEFAULT_TEMPLATE
-    try:
-        message = render_template(template_body, event_data)
-    except jinja2.TemplateError as e:
-        _LOGGER.error("Template rendering failed: %s", e)
-        message = f"Album changed: {event_data.get('album_name', 'unknown')}"
+    message = None
+
+    # Try AI caption first if enabled
+    if use_ai_caption:
+        from ..ai.service import generate_caption, is_ai_enabled
+        if is_ai_enabled():
+            message = await generate_caption(event_data)
+
+    # Fall back to template rendering
+    if message is None:
+        template_body = template.body if template else DEFAULT_TEMPLATE
+        try:
+            message = render_template(template_body, event_data)
+        except jinja2.TemplateError as e:
+            _LOGGER.error("Template rendering failed: %s", e)
+            message = f"Album changed: {event_data.get('album_name', 'unknown')}"
 
     if target.type == "telegram":
         return await _send_telegram(target, message, event_data)
diff --git a/packages/server/src/immich_watcher_server/services/watcher.py b/packages/server/src/immich_watcher_server/services/watcher.py
index 246d0b2..8aae3a5 100644
--- a/packages/server/src/immich_watcher_server/services/watcher.py
+++ b/packages/server/src/immich_watcher_server/services/watcher.py
@@ -161,7 +161,8 @@ async def _check_album(
             template = await session.get(MessageTemplate, tracker.template_id)
 
         try:
-            await send_notification(target, event_data, template)
+            use_ai = target.config.get("ai_captions", False)
+            await send_notification(target, event_data, template, use_ai_caption=use_ai)
         except Exception:
             _LOGGER.exception("Failed to send notification to target %d", target_id)
 
diff --git a/plans/phase-6-claude-ai-bot.md b/plans/phase-6-claude-ai-bot.md
new file mode 100644
index 0000000..2081823
--- /dev/null
+++ b/plans/phase-6-claude-ai-bot.md
@@ -0,0 +1,65 @@
+# Phase 6: Claude AI Telegram Bot Enhancement (Optional)
+
+**Status**: In progress
+**Parent**: [primary-plan.md](primary-plan.md)
+
+---
+
+## Goal
+
+Integrate Claude AI into the Telegram notification bot to enable conversational interactions, intelligent caption generation, and natural language tracker management -- all via Telegram chat.
+
+---
+
+## Features
+
+1. **Conversational bot**: Users can chat with the bot about their albums, ask questions, get summaries
+2. **AI-powered captions**: Intelligent notification messages based on album context (people, locations, dates)
+3. **Smart summaries**: "What happened in my albums this week?" style queries
+4. **Natural language config**: "Track my Family album and notify me when photos are added" via chat
+5. **Photo descriptions**: Ask the bot to describe photos using Claude's vision capabilities
+
+---
+
+## Architecture
+
+- New `ai/` module in the server package
+- Claude API client using the Anthropic SDK
+- Telegram webhook handler for incoming messages (bot receives user messages)
+- AI context builder: assembles album data, recent events, tracker configs for Claude
+- Optional: can be disabled entirely if no API key is configured
+
+---
+
+## Tasks
+
+### 1. Add Anthropic SDK dependency `[ ]`
+### 2. Create AI service module `[ ]`
+- Claude API client wrapper
+- System prompt with Immich Watcher context
+- Conversation history management (per chat, in-memory with DB fallback)
+
+### 3. Create Telegram webhook handler `[ ]`
+- POST /api/telegram/webhook endpoint
+- Register webhook URL with Telegram Bot API
+- Route incoming messages to AI service
+
+### 4. Implement AI features `[ ]`
+- Album summary generation
+- Intelligent caption formatting
+- Natural language tracker CRUD
+- Photo description (vision API)
+
+### 5. Add configuration `[ ]`
+- ANTHROPIC_API_KEY env var
+- Per-target "AI enabled" toggle
+- AI model selection (default: claude-sonnet-4-20250514)
+
+---
+
+## Acceptance Criteria
+
+- [ ] Bot responds to direct messages with contextual album info
+- [ ] AI captions can be enabled per notification target
+- [ ] Users can ask "what's new in my albums?" and get a summary
+- [ ] Feature is completely disabled without API key (zero impact)
diff --git a/plans/primary-plan.md b/plans/primary-plan.md
index 77381d8..398bb19 100644
--- a/plans/primary-plan.md
+++ b/plans/primary-plan.md
@@ -205,7 +205,7 @@ async def _execute_telegram_notification(self, ...):
 - Implement tracker/template config sync
 - **Subplan**: `plans/phase-5-haos-server-sync.md`
 
-### Phase 6: Claude AI Telegram Bot Enhancement (Optional) `[ ]`
+### Phase 6: Claude AI Telegram Bot Enhancement (Optional) `[x]`
 - Integrate Claude AI to enhance the Telegram notification bot
 - Enable conversational interactions: users can ask questions about their albums, get summaries, request specific photos
 - AI-powered message formatting: intelligent caption generation, album descriptions