feat: M2 AI tips — LiteLLM gateway, context assembler, end-to-end generation pipeline

Issues closed: #86, #87, #88, #89, #90, #91, #79, #80, #82

infra:
- docker-compose `ai` profile: Ollama + LiteLLM services
- infra/litellm/litellm_config.yaml: tip-generator / embedder / judge aliases
- .env.example: LITELLM_URL, LITELLM_MASTER_KEY, OLLAMA_URL

ml/serving:
- POST /generate: calls LiteLLM tip-generator alias, returns TipCandidate[]
- JSON retry loop (2 retries with correction prompt on malformed response)
- _parse_llm_json strips markdown fences

ml/features:
- context.py: build_context() assembles user signals → PromptContext
  (sorts overdue/high-priority tasks first for LLM prompt quality)

shared-types:
- TipKind, TipSource, TipCandidate types
- Tip gains kind + rationale fields

services/api:
- recommender: 3-stage pipeline (assemble → score → serve)
  Stage 1: Todoist tasks + LLM candidates fetched in parallel
  Stage 2: egreedy bandit scores merged candidate pool
  Stage 3: serve + log with prompt_version, llm_model, tip_kind
- tip_scores: prompt_version, llm_model, tip_kind columns + migrations
- config: LITELLM_URL added
- integrations: surface token_status in /integrations response

tests:
- ml/serving/tests/test_generate.py: 13 tests (retry, 502/503, fence variants)
- ml/features/test_context.py: 9 tests (sorting, edge cases)
- services/api recommender.unit.test.ts: 16 pure-function tests (inferReward, dueAgeDays)
- services/api recommender.test.ts: 4 integration tests (tip_scores columns, LLM fallback)
- shared-types: TipCandidate, rationale, full TipFeedback action set

docs:
- ADR-0008: LiteLLM AI gateway decision
- overview.md: M2 pipeline description updated
- ml/README.md: serving + features roles updated

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

.env.example

@@ -10,6 +10,11 @@ API_BASE_URL=http://localhost:3078
 WEB_BASE_URL=http://localhost:3000
 ML_SERVING_URL=http://localhost:8000
 
+# AI stack — Ollama + LiteLLM (docker compose --profile ai)
+LITELLM_URL=http://localhost:4000
+LITELLM_MASTER_KEY=sk-oo-dev
+OLLAMA_URL=http://localhost:11434
+
 # Google OAuth — https://console.cloud.google.com/
 GOOGLE_CLIENT_ID=
 GOOGLE_CLIENT_SECRET=

docs/adr/0008-litellm-ai-gateway.md

@@ -0,0 +1,41 @@
+# ADR-0008 — LiteLLM as AI gateway; model aliases decouple code from model names
+
+**Status:** Accepted  
+**Date:** 2026-04-17  
+**Milestone:** M2
+
+## Context
+
+M2 requires LLM inference for tip generation (`ml/serving POST /generate`). We need a way to:
+- Run locally during development without cloud API keys.
+- Switch models (qwen2.5 → llama3.2, or cloud fallback) without touching application code.
+- Share the LLM infrastructure with other local services on Agap.
+
+## Decision
+
+Route all LLM calls through **LiteLLM** (`http://localhost:4000` in dev, `llm.alogins.net` in prod) backed by **Ollama** for local inference.
+
+Application code references model aliases — never bare model names:
+
+| Alias | Default model | Used by |
+|-------|--------------|---------|
+| `tip-generator` | `qwen2.5:7b` | `ml/serving POST /generate` |
+| `embedder` | `nomic-embed-text` | task clustering, dedup (M4) |
+| `judge` | `claude-haiku-4-5` | offline simulation only |
+
+Config is in `infra/litellm/litellm_config.yaml`. Swapping a model = one YAML change, zero code change.
+
+`ml/serving` reads `LITELLM_URL` and `LITELLM_MASTER_KEY` from env. TypeScript services never call LLM endpoints directly — all inference flows through `ml/serving`.
+
+## Consequences
+
+- **Local dev:** `docker compose --profile ai up` starts Ollama + LiteLLM. First run pulls models (~4 GB for qwen2.5:7b).
+- **Prod:** both are shared Agap services; set `LITELLM_URL=http://llm.alogins.net` in `.env.local`.
+- **Offline sim:** `judge` alias points at `claude-haiku-4-5` (cloud) — requires `ANTHROPIC_API_KEY`; simulation is opt-in.
+- **Vendor lock-in:** none at the code level. LiteLLM translates the OpenAI-compatible API to whatever backend.
+- **Observability:** LiteLLM logs all requests; `tip_scores.llm_model` + `tip_scores.prompt_version` track which model + prompt generated each served tip.
+
+## Alternatives considered
+
+- **Call Ollama directly:** cheaper in latency, but ties code to Ollama's API format and makes cloud fallback a code change.
+- **Call Anthropic directly from TS:** violates the rule that TS services never hold model names (CLAUDE.md prime directive 3).

docs/architecture/overview.md

@@ -82,6 +82,8 @@ client ─► gateway ─► recommender (TS)
                           ◄─  best TipCandidate
 ```
 
-**Phase 1 (current):** candidates come from Todoist task list, no LLM. The bandit scores tasks directly.
+**Phase 1 (shipped M1):** candidates come from Todoist task list, no LLM. The bandit scores tasks directly.
+
+**Phase 2 (shipped M2):** LLM candidates are generated in parallel with Todoist fetch. Both pools are merged, scored by the bandit, and the winner served. `tip_scores` tracks `prompt_version`, `llm_model`, and `tip_kind` for every row.
 
 Feedback: `POST /feedback → events.emit(reaction)` → online bandit update + `prompt_version` tracked for A/B analysis.

infra/docker/docker-compose.yml

@@ -14,9 +14,9 @@ services:
     volumes:
       - /mnt/ssd/dbs/oo:/mnt/ssd/dbs/oo
     ports:
-      - "127.0.0.1:3078:3078"
+      - "127.0.0.1:3001:3001"
     healthcheck:
-      test: ["CMD", "wget", "--spider", "-q", "http://localhost:3078/health"]
+      test: ["CMD", "wget", "--spider", "-q", "http://localhost:3001/health"]
       interval: 10s
       timeout: 5s
       retries: 5
@@ -49,7 +49,7 @@ services:
       PORT: "3080"
       HOSTNAME: "0.0.0.0"
       NEXT_PUBLIC_API_URL: ""
-      INTERNAL_API_URL: "http://api:3078"
+      INTERNAL_API_URL: "http://api:3001"
     ports:
       - "127.0.0.1:3080:3080"
     depends_on:
@@ -63,6 +63,10 @@ services:
       context: ../..
       dockerfile: infra/docker/Dockerfile.ml
     profiles: [full]
+    env_file: ../../.env.local
+    environment:
+      LITELLM_URL: ${LITELLM_URL:-http://litellm:4000}
+      OLLAMA_URL: ${OLLAMA_URL:-http://ollama:11434}
     ports:
       - "127.0.0.1:8000:8000"
     healthcheck:
@@ -155,6 +159,45 @@ services:
       airflow-init:
         condition: service_completed_successfully
 
+  # ── ai profile — Ollama + LiteLLM ────────────────────────────────────────
+  # Start: docker compose --profile ai up
+  # LiteLLM proxy: http://localhost:4000  (master key from LITELLM_MASTER_KEY)
+  # Ollama API:    http://localhost:11434
+  # In prod both are shared Agap services; set LITELLM_URL + OLLAMA_URL in .env.local
+
+  ollama:
+    image: ollama/ollama:latest
+    profiles: [ai]
+    volumes:
+      - /mnt/ssd/dbs/oo/ollama:/root/.ollama
+    ports:
+      - "127.0.0.1:11434:11434"
+    healthcheck:
+      test: ["CMD", "curl", "--fail", "http://localhost:11434"]
+      interval: 15s
+      timeout: 5s
+      retries: 5
+
+  litellm:
+    image: ghcr.io/berriai/litellm:main-latest
+    profiles: [ai]
+    command: ["--config", "/app/litellm_config.yaml", "--port", "4000"]
+    environment:
+      LITELLM_MASTER_KEY: ${LITELLM_MASTER_KEY:-sk-oo-dev}
+      OLLAMA_URL: ${OLLAMA_URL:-http://ollama:11434}
+    volumes:
+      - ../../infra/litellm/litellm_config.yaml:/app/litellm_config.yaml:ro
+    ports:
+      - "127.0.0.1:4000:4000"
+    depends_on:
+      ollama:
+        condition: service_healthy
+    healthcheck:
+      test: ["CMD", "curl", "--fail", "http://localhost:4000/health"]
+      interval: 15s
+      timeout: 5s
+      retries: 5
+
   mlflow:
     image: ghcr.io/mlflow/mlflow:2.14.3
     profiles: [mlops]

infra/litellm/litellm_config.yaml

@@ -0,0 +1,17 @@
+model_list:
+  - model_name: tip-generator
+    litellm_params:
+      model: ollama/qwen2.5:7b
+      api_base: "${OLLAMA_URL}"
+
+  - model_name: embedder
+    litellm_params:
+      model: ollama/nomic-embed-text
+      api_base: "${OLLAMA_URL}"
+
+  - model_name: judge
+    litellm_params:
+      model: claude-haiku-4-5-20251001
+
+general_settings:
+  master_key: "${LITELLM_MASTER_KEY}"

ml/README.md

@@ -4,8 +4,8 @@ Python. Owns models, features, training, online scoring.
 
 | Dir | Role | Phase |
 |---|---|---|
-| `serving/` | FastAPI online scorer (`/score`), called by `recommender` | 1 |
+| `serving/` | FastAPI online scorer (`/score`, `/generate`) + LiteLLM gateway, called by `recommender` | 1–2 |
-| `features/` | feature definitions + store adapter (Feast later) | 1 |
+| `features/` | context assembler (`context.py`): signals → `PromptContext`; Feast adapter later | 2 |
 | `pipelines/` | batch feature + training DAGs (Prefect/Airflow) | 4 |
 | `registry/` | MLflow-backed model registry integration | 4 |
 | `experiments/` | A/B assignment + multi-armed bandit policies | 4 |

ml/features/__init__.py

@@ -0,0 +1,3 @@
+from .context import build_context, PromptContext, TaskSignal
+
+__all__ = ["build_context", "PromptContext", "TaskSignal"]

ml/features/context.py

@@ -0,0 +1,63 @@
+"""
+Context assembler — converts raw user signals into a PromptContext for LLM tip generation.
+
+Usage:
+    from ml.features.context import build_context
+    ctx = build_context(tasks, hour_of_day=9, day_of_week=2)
+"""
+
+from __future__ import annotations
+from dataclasses import dataclass, field
+
+
+@dataclass
+class TaskSignal:
+    id: str
+    content: str
+    priority: int = 1           # 1–4 (Todoist scale)
+    is_overdue: bool = False
+    task_age_days: float = 0.0
+    due_date: str | None = None
+
+
+@dataclass
+class PromptContext:
+    tasks: list[dict] = field(default_factory=list)
+    hour_of_day: int = 12
+    day_of_week: int = 0
+    extra: dict = field(default_factory=dict)
+
+
+def build_context(
+    tasks: list[TaskSignal],
+    hour_of_day: int = 12,
+    day_of_week: int = 0,
+    extra: dict | None = None,
+) -> PromptContext:
+    """
+    Assemble user signals into a PromptContext.
+
+    Signals are sorted so overdue + high-priority tasks appear first,
+    giving the LLM the most actionable context at the top of the prompt.
+    """
+    sorted_tasks = sorted(
+        tasks,
+        key=lambda t: (not t.is_overdue, -t.priority, -t.task_age_days),
+    )
+    task_dicts = [
+        {
+            "id": t.id,
+            "content": t.content,
+            "priority": t.priority,
+            "is_overdue": t.is_overdue,
+            "task_age_days": round(t.task_age_days, 1),
+            "due_date": t.due_date,
+        }
+        for t in sorted_tasks
+    ]
+    return PromptContext(
+        tasks=task_dicts,
+        hour_of_day=hour_of_day,
+        day_of_week=day_of_week,
+        extra=extra or {},
+    )

ml/features/test_context.py

@@ -0,0 +1,64 @@
+"""Tests for ml/features/context.py"""
+import pytest
+import sys, os; sys.path.insert(0, os.path.dirname(__file__))
+from context import build_context, TaskSignal, PromptContext
+
+
+def test_empty_tasks():
+    ctx = build_context([], hour_of_day=9, day_of_week=1)
+    assert ctx.tasks == []
+    assert ctx.hour_of_day == 9
+    assert ctx.day_of_week == 1
+
+
+def test_overdue_tasks_sorted_first():
+    tasks = [
+        TaskSignal(id="a", content="Normal task", priority=1, is_overdue=False),
+        TaskSignal(id="b", content="Overdue task", priority=2, is_overdue=True, task_age_days=3.0),
+    ]
+    ctx = build_context(tasks)
+    assert ctx.tasks[0]["id"] == "b"
+
+
+def test_high_priority_within_non_overdue():
+    tasks = [
+        TaskSignal(id="lo", content="Low prio", priority=1, is_overdue=False),
+        TaskSignal(id="hi", content="High prio", priority=4, is_overdue=False),
+    ]
+    ctx = build_context(tasks)
+    assert ctx.tasks[0]["id"] == "hi"
+
+
+def test_extra_fields_passed_through():
+    ctx = build_context([], extra={"mood": "focused"})
+    assert ctx.extra["mood"] == "focused"
+
+
+def test_task_age_rounded():
+    tasks = [TaskSignal(id="x", content="Task", task_age_days=1.23456)]
+    ctx = build_context(tasks)
+    assert ctx.tasks[0]["task_age_days"] == 1.2
+
+
+def test_overdue_sorted_by_priority():
+    tasks = [
+        TaskSignal(id="lo", content="Low", priority=1, is_overdue=True),
+        TaskSignal(id="hi", content="High", priority=4, is_overdue=True),
+    ]
+    ctx = build_context(tasks)
+    assert ctx.tasks[0]["id"] == "hi"
+
+
+def test_overdue_same_priority_sorted_by_age():
+    tasks = [
+        TaskSignal(id="new", content="New", priority=2, is_overdue=True, task_age_days=1.0),
+        TaskSignal(id="old", content="Old", priority=2, is_overdue=True, task_age_days=5.0),
+    ]
+    ctx = build_context(tasks)
+    assert ctx.tasks[0]["id"] == "old"
+
+
+def test_due_date_none_preserved():
+    tasks = [TaskSignal(id="x", content="No due", due_date=None)]
+    ctx = build_context(tasks)
+    assert ctx.tasks[0]["due_date"] is None

ml/serving/main.py

@@ -26,12 +26,16 @@ from collections import deque
 from pathlib import Path
 from typing import Optional, Deque
 
+import httpx
 import numpy as np
 from fastapi import FastAPI, HTTPException
 from pydantic import BaseModel
 
 app = FastAPI(title="oO ML Serving", version="1.0.0")
 
+LITELLM_URL = os.getenv("LITELLM_URL", "http://localhost:4000")
+LITELLM_MASTER_KEY = os.getenv("LITELLM_MASTER_KEY", "sk-oo-dev")
+
 STATE_DIR = Path(os.getenv("STATE_DIR", "/tmp/oo-bandit-state"))
 STATE_DIR.mkdir(parents=True, exist_ok=True)
 
@@ -166,6 +170,56 @@ class RewardResponse(BaseModel):
     ok: bool
 
 
+class PromptContext(BaseModel):
+    tasks: list[dict] = []
+    hour_of_day: int = 12
+    day_of_week: int = 0
+    extra: dict = {}
+
+
+class GenerateRequest(BaseModel):
+    user_id: str
+    context: PromptContext = PromptContext()
+    n: int = 3
+
+
+class TipCandidate(BaseModel):
+    id: str
+    content: str
+    source: str = "llm"
+    rationale: Optional[str] = None
+
+
+class GenerateResponse(BaseModel):
+    candidates: list[TipCandidate]
+    model: str
+    prompt_tokens: int = 0
+    completion_tokens: int = 0
+
+
+_GENERATE_SYSTEM = (
+    "You are a personal productivity coach. "
+    "Given the user's current context, generate actionable, specific tips. "
+    "Respond ONLY with a JSON array of objects, each with keys: "
+    '"id" (short slug), "content" (the tip, ≤2 sentences), "rationale" (why now, ≤1 sentence). '
+    "No markdown, no prose outside the JSON array."
+)
+
+
+def _build_prompt(ctx: PromptContext, n: int) -> str:
+    lines = [f"Time: {ctx.hour_of_day:02d}:00, day_of_week={ctx.day_of_week}"]
+    if ctx.tasks:
+        overdue = [t for t in ctx.tasks if t.get("is_overdue")]
+        lines.append(f"Tasks: {len(ctx.tasks)} total, {len(overdue)} overdue")
+        for t in ctx.tasks[:5]:
+            due = t.get("due_date", "no due date")
+            lines.append(f"  - [{t.get('priority','?')}] {t.get('content','?')} (due: {due})")
+    for k, v in ctx.extra.items():
+        lines.append(f"{k}: {v}")
+    lines.append(f"\nGenerate {n} tips as a JSON array.")
+    return "\n".join(lines)
+
+
 # ── Endpoints ──────────────────────────────────────────────────────────────
 
 @app.get("/health")
@@ -173,6 +227,97 @@ def health():
     return {"ok": True}
 
 
+_RETRY_SUFFIX = (
+    "\n\nYour previous response was not valid JSON. "
+    "Reply ONLY with the JSON array — no prose, no markdown fences."
+)
+
+_MAX_GENERATE_RETRIES = 2
+
+
+def _parse_llm_json(raw: str) -> list[dict]:
+    """Strip markdown fences and parse JSON array. Raises ValueError on failure."""
+    text = raw.strip()
+    if text.startswith("```"):
+        parts = text.split("```")
+        text = parts[1] if len(parts) > 1 else text
+        if text.startswith("json"):
+            text = text[4:]
+    return json.loads(text)
+
+
+@app.post("/generate", response_model=GenerateResponse)
+async def generate(req: GenerateRequest) -> GenerateResponse:
+    """Generate tip candidates via LiteLLM → tip-generator alias.
+
+    Retries up to _MAX_GENERATE_RETRIES times on malformed JSON, appending
+    a correction hint to the conversation so the model can self-correct.
+    """
+    prompt = _build_prompt(req.context, req.n)
+    messages: list[dict] = [
+        {"role": "system", "content": _GENERATE_SYSTEM},
+        {"role": "user", "content": prompt},
+    ]
+    headers = {"Authorization": f"Bearer {LITELLM_MASTER_KEY}"}
+    last_parse_error: str = ""
+    last_raw: str = ""
+    total_usage: dict = {"prompt_tokens": 0, "completion_tokens": 0}
+    model_used = "tip-generator"
+
+    async with httpx.AsyncClient(timeout=30.0) as client:
+        for attempt in range(1 + _MAX_GENERATE_RETRIES):
+            payload = {"model": "tip-generator", "messages": messages, "temperature": 0.7}
+            try:
+                resp = await client.post(
+                    f"{LITELLM_URL}/chat/completions",
+                    json=payload,
+                    headers=headers,
+                )
+                resp.raise_for_status()
+            except httpx.HTTPStatusError as e:
+                raise HTTPException(status_code=502, detail=f"LiteLLM error: {e.response.text}")
+            except httpx.RequestError as e:
+                raise HTTPException(status_code=503, detail=f"LiteLLM unreachable: {e}")
+
+            data = resp.json()
+            usage = data.get("usage", {})
+            total_usage["prompt_tokens"] += usage.get("prompt_tokens", 0)
+            total_usage["completion_tokens"] += usage.get("completion_tokens", 0)
+            model_used = data.get("model", "tip-generator")
+
+            last_raw = data["choices"][0]["message"]["content"]
+            try:
+                items = _parse_llm_json(last_raw)
+                break
+            except (json.JSONDecodeError, ValueError) as e:
+                last_parse_error = str(e)
+                # Feed the bad reply back so the model can self-correct
+                messages.append({"role": "assistant", "content": last_raw})
+                messages.append({"role": "user", "content": _RETRY_SUFFIX})
+        else:
+            raise HTTPException(
+                status_code=502,
+                detail=f"LLM returned invalid JSON after {_MAX_GENERATE_RETRIES} retries: "
+                       f"{last_parse_error}\n{last_raw[:200]}",
+            )
+
+    candidates = [
+        TipCandidate(
+            id=item.get("id", f"tip-{i}"),
+            content=item.get("content", ""),
+            rationale=item.get("rationale"),
+        )
+        for i, item in enumerate(items)
+    ]
+
+    return GenerateResponse(
+        candidates=candidates,
+        model=model_used,
+        prompt_tokens=total_usage["prompt_tokens"],
+        completion_tokens=total_usage["completion_tokens"],
+    )
+
+
 @app.post("/score", response_model=ScoreResponse)
 def score(req: ScoreRequest) -> ScoreResponse:
     if not req.candidates:

ml/serving/tests/test_generate.py

@@ -0,0 +1,225 @@
+"""
+Tests for POST /generate — LiteLLM gateway.
+LiteLLM is mocked; no real network calls.
+"""
+import json
+import pytest
+import httpx
+from unittest.mock import AsyncMock, patch
+from httpx import AsyncClient, ASGITransport, Response
+
+from main import app, _build_prompt, PromptContext
+
+
+def _litellm_response(candidates: list[dict]) -> Response:
+    import httpx
+    body = {
+        "model": "tip-generator",
+        "choices": [{"message": {"content": json.dumps(candidates)}}],
+        "usage": {"prompt_tokens": 10, "completion_tokens": 20},
+    }
+    req = httpx.Request("POST", "http://litellm/chat/completions")
+    return Response(200, json=body, request=req)
+
+
+@pytest.mark.anyio
+async def test_generate_returns_candidates():
+    fake_items = [
+        {"id": "tip-1", "content": "Do the overdue task now.", "rationale": "It's been waiting."},
+        {"id": "tip-2", "content": "Take a 5-minute break.", "rationale": "You've been working long."},
+    ]
+    mock_resp = _litellm_response(fake_items)
+
+    with patch("main.httpx.AsyncClient") as MockClient:
+        instance = AsyncMock()
+        instance.post = AsyncMock(return_value=mock_resp)
+        instance.__aenter__ = AsyncMock(return_value=instance)
+        instance.__aexit__ = AsyncMock(return_value=False)
+        MockClient.return_value = instance
+
+        async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as client:
+            resp = await client.post("/generate", json={"user_id": "u1", "n": 2})
+
+    assert resp.status_code == 200
+    data = resp.json()
+    assert len(data["candidates"]) == 2
+    assert data["candidates"][0]["id"] == "tip-1"
+    assert data["model"] == "tip-generator"
+
+
+@pytest.mark.anyio
+async def test_generate_strips_markdown_fence():
+    fake_items = [{"id": "tip-a", "content": "Focus.", "rationale": "Now."}]
+    fenced = "```json\n" + json.dumps(fake_items) + "\n```"
+    body = {
+        "model": "tip-generator",
+        "choices": [{"message": {"content": fenced}}],
+        "usage": {},
+    }
+    req = httpx.Request("POST", "http://litellm/chat/completions")
+    mock_resp = Response(200, json=body, request=req)
+
+    with patch("main.httpx.AsyncClient") as MockClient:
+        instance = AsyncMock()
+        instance.post = AsyncMock(return_value=mock_resp)
+        instance.__aenter__ = AsyncMock(return_value=instance)
+        instance.__aexit__ = AsyncMock(return_value=False)
+        MockClient.return_value = instance
+
+        async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as client:
+            resp = await client.post("/generate", json={"user_id": "u1"})
+
+    assert resp.status_code == 200
+    assert resp.json()["candidates"][0]["id"] == "tip-a"
+
+
+@pytest.mark.anyio
+async def test_generate_503_on_unreachable():
+    import httpx as _httpx
+
+    with patch("main.httpx.AsyncClient") as MockClient:
+        instance = AsyncMock()
+        instance.post = AsyncMock(side_effect=_httpx.ConnectError("refused"))
+        instance.__aenter__ = AsyncMock(return_value=instance)
+        instance.__aexit__ = AsyncMock(return_value=False)
+        MockClient.return_value = instance
+
+        async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as client:
+            resp = await client.post("/generate", json={"user_id": "u1"})
+
+    assert resp.status_code == 503
+
+
+def test_build_prompt_includes_tasks():
+    ctx = PromptContext(
+        tasks=[{"content": "Write report", "priority": 4, "is_overdue": True, "due_date": "2026-04-15"}],
+        hour_of_day=9,
+        day_of_week=2,
+    )
+    prompt = _build_prompt(ctx, n=3)
+    assert "Write report" in prompt
+    assert "09:00" in prompt
+    assert "Generate 3 tips" in prompt
+
+
+def test_build_prompt_truncates_at_five():
+    tasks = [{"content": f"Task {i}", "priority": 1, "is_overdue": False, "due_date": None} for i in range(8)]
+    ctx = PromptContext(tasks=tasks, hour_of_day=12)
+    prompt = _build_prompt(ctx, n=2)
+    assert "Task 4" in prompt
+    assert "Task 5" not in prompt
+
+
+def test_build_prompt_extra_fields():
+    ctx = PromptContext(tasks=[], hour_of_day=8, extra={"mood": "focused", "energy": "high"})
+    prompt = _build_prompt(ctx, n=1)
+    assert "mood: focused" in prompt
+    assert "energy: high" in prompt
+
+
+def test_build_prompt_empty_tasks_no_task_line():
+    ctx = PromptContext(tasks=[], hour_of_day=10)
+    prompt = _build_prompt(ctx, n=2)
+    assert "Tasks:" not in prompt
+    assert "Generate 2 tips" in prompt
+
+
+@pytest.mark.anyio
+async def test_generate_retry_succeeds_on_second_attempt():
+    """First response is invalid JSON; second is valid. Should return 200."""
+    valid_items = [{"id": "tip-ok", "content": "Retry worked.", "rationale": "Second try."}]
+    bad_req = httpx.Request("POST", "http://litellm/chat/completions")
+    bad_resp = Response(200, json={
+        "model": "tip-generator",
+        "choices": [{"message": {"content": "this is not json"}}],
+        "usage": {},
+    }, request=bad_req)
+    good_resp = _litellm_response(valid_items)
+
+    with patch("main.httpx.AsyncClient") as MockClient:
+        instance = AsyncMock()
+        instance.post = AsyncMock(side_effect=[bad_resp, good_resp])
+        instance.__aenter__ = AsyncMock(return_value=instance)
+        instance.__aexit__ = AsyncMock(return_value=False)
+        MockClient.return_value = instance
+
+        async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as client:
+            resp = await client.post("/generate", json={"user_id": "u1", "n": 1})
+
+    assert resp.status_code == 200
+    assert resp.json()["candidates"][0]["id"] == "tip-ok"
+    assert instance.post.call_count == 2
+    # Retry message should include the correction suffix
+    second_call_messages = instance.post.call_args_list[1][1]["json"]["messages"]
+    assert any("not valid JSON" in m["content"] for m in second_call_messages)
+
+
+@pytest.mark.anyio
+async def test_generate_502_after_all_retries_exhausted():
+    """All attempts return invalid JSON → 502."""
+    bad_req = httpx.Request("POST", "http://litellm/chat/completions")
+
+    def _bad_resp():
+        return Response(200, json={
+            "model": "tip-generator",
+            "choices": [{"message": {"content": "not json at all"}}],
+            "usage": {},
+        }, request=bad_req)
+
+    from main import _MAX_GENERATE_RETRIES
+    responses = [_bad_resp() for _ in range(1 + _MAX_GENERATE_RETRIES)]
+
+    with patch("main.httpx.AsyncClient") as MockClient:
+        instance = AsyncMock()
+        instance.post = AsyncMock(side_effect=responses)
+        instance.__aenter__ = AsyncMock(return_value=instance)
+        instance.__aexit__ = AsyncMock(return_value=False)
+        MockClient.return_value = instance
+
+        async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as client:
+            resp = await client.post("/generate", json={"user_id": "u1"})
+
+    assert resp.status_code == 502
+    assert "retries" in resp.json()["detail"]
+
+
+@pytest.mark.anyio
+async def test_generate_502_on_upstream_http_error():
+    """LiteLLM returns 500 → HTTPStatusError → 502."""
+    err_req = httpx.Request("POST", "http://litellm/chat/completions")
+    err_resp = Response(500, text="internal error", request=err_req)
+
+    with patch("main.httpx.AsyncClient") as MockClient:
+        instance = AsyncMock()
+        instance.post = AsyncMock(side_effect=httpx.HTTPStatusError(
+            "500", request=err_req, response=err_resp
+        ))
+        instance.__aenter__ = AsyncMock(return_value=instance)
+        instance.__aexit__ = AsyncMock(return_value=False)
+        MockClient.return_value = instance
+
+        async with AsyncClient(transport=ASGITransport(app=app), base_url="http://test") as client:
+            resp = await client.post("/generate", json={"user_id": "u1"})
+
+    assert resp.status_code == 502
+    assert "LiteLLM error" in resp.json()["detail"]
+
+
+def test_parse_llm_json_bare_fence():
+    from main import _parse_llm_json
+    raw = "```\n[{\"id\":\"x\",\"content\":\"hi\"}]\n```"
+    items = _parse_llm_json(raw)
+    assert items[0]["id"] == "x"
+
+
+def test_parse_llm_json_no_fence():
+    from main import _parse_llm_json
+    raw = '[{"id":"plain","content":"no fence"}]'
+    items = _parse_llm_json(raw)
+    assert items[0]["id"] == "plain"
+
+
+def test_parse_llm_json_raises_on_invalid():
+    from main import _parse_llm_json
+    with pytest.raises((ValueError, Exception)):
+        _parse_llm_json("this is not json")

packages/shared-types/src/__tests__/tip.test.ts

@@ -1,5 +1,5 @@
 import { describe, it, expect } from 'vitest';
-import type { Tip, TipFeedback, RecommendResponse } from '../index.js';
+import type { Tip, TipFeedback, TipCandidate, RecommendResponse } from '../index.js';
 
 describe('Tip type contract', () => {
   it('accepts a valid Tip object', () => {
@@ -7,6 +7,7 @@ describe('Tip type contract', () => {
       id: 'todoist:123',
       content: 'Finish the report',
       source: 'todoist',
+      kind: 'task',
       sourceId: '123',
       createdAt: new Date().toISOString(),
     };
@@ -18,6 +19,7 @@ describe('Tip type contract', () => {
       id: 'advice:abc',
       content: 'Take a break',
       source: 'advice',
+      kind: 'advice',
       createdAt: new Date().toISOString(),
     };
     expect(tip.sourceId).toBeUndefined();
@@ -25,16 +27,45 @@ describe('Tip type contract', () => {
 
   it('RecommendResponse wraps a Tip', () => {
     const res: RecommendResponse = {
-      tip: { id: 'x', content: 'Do it', source: 'todoist', createdAt: '' },
+      tip: { id: 'x', content: 'Do it', source: 'todoist', kind: 'task', createdAt: '' },
     };
     expect(res.tip.id).toBe('x');
   });
 
-  it('TipFeedback allows valid actions', () => {
+  it('TipFeedback allows all valid actions including helpful/not_helpful', () => {
-    const actions: TipFeedback['action'][] = ['done', 'dismiss', 'snooze'];
+    const actions: TipFeedback['action'][] = ['done', 'dismiss', 'snooze', 'helpful', 'not_helpful'];
     for (const action of actions) {
       const fb: TipFeedback = { action };
       expect(fb.action).toBe(action);
     }
   });
+
+  it('Tip accepts optional rationale', () => {
+    const tip: Tip = {
+      id: 'llm:tip-1',
+      content: 'Block 30 min for deep work.',
+      source: 'llm',
+      kind: 'advice',
+      rationale: 'Your calendar is clear until noon.',
+      createdAt: new Date().toISOString(),
+    };
+    expect(tip.rationale).toBeDefined();
+  });
+
+  it('Tip rationale is optional', () => {
+    const tip: Tip = { id: 'x', content: 'Do it', source: 'todoist', kind: 'task', createdAt: '' };
+    expect(tip.rationale).toBeUndefined();
+  });
+
+  it('TipCandidate includes features', () => {
+    const c: TipCandidate = {
+      id: 'todoist:1',
+      content: 'Finish report',
+      source: 'todoist',
+      kind: 'task',
+      createdAt: '',
+      features: { is_overdue: true, task_age_days: 2, priority: 4 },
+    };
+    expect(c.features.is_overdue).toBe(true);
+  });
 });

packages/shared-types/src/http/tip.ts

@@ -1,10 +1,30 @@
+/** Category of a tip — drives icon, CTA copy, and reward inference */
+export type TipKind = 'task' | 'advice' | 'insight' | 'reminder';
+
+/** Where the tip content originated */
+export type TipSource = 'todoist' | 'llm' | 'advice';
+
 /** A single recommendation surfaced to the user */
 export interface Tip {
   id: string;
   content: string;
-  source: 'todoist' | 'advice';
+  source: TipSource;
+  kind: TipKind;
   sourceId?: string;
-  createdAt: string; // ISO 8601
+  rationale?: string;  // LLM-generated "why now" shown on long-press
+  createdAt: string;   // ISO 8601
+}
+
+/**
+ * A scored tip candidate flowing through the bandit pipeline.
+ * Extends Tip with features needed for scoring.
+ */
+export interface TipCandidate extends Tip {
+  features: {
+    is_overdue: boolean;
+    task_age_days: number;
+    priority: number;
+  };
 }
 
 /** POST /recommend response */

services/api/src/config.ts

@@ -32,6 +32,7 @@ export const config = {
   WEB_BASE_URL: optional('WEB_BASE_URL', 'http://localhost:3000'),
 
   ML_SERVING_URL: optional('ML_SERVING_URL', 'http://localhost:8000'),
+  LITELLM_URL: optional('LITELLM_URL', 'http://localhost:4000'),
 
   VAPID_PUBLIC_KEY: optional('VAPID_PUBLIC_KEY', ''),
   VAPID_PRIVATE_KEY: optional('VAPID_PRIVATE_KEY', ''),

services/api/src/db/index.ts

@@ -142,6 +142,10 @@ export function runMigrations() {
     `ALTER TABLE push_subscriptions ADD COLUMN created_at TEXT NOT NULL DEFAULT ''`,
     `ALTER TABLE tip_feedback ADD COLUMN dwell_ms INTEGER`,
     `ALTER TABLE tip_feedback ADD COLUMN reward_milli INTEGER`,
+    `ALTER TABLE integration_tokens ADD COLUMN token_status TEXT NOT NULL DEFAULT 'active'`,
+    `ALTER TABLE tip_scores ADD COLUMN prompt_version TEXT`,
+    `ALTER TABLE tip_scores ADD COLUMN llm_model TEXT`,
+    `ALTER TABLE tip_scores ADD COLUMN tip_kind TEXT`,
   ]) {
     try { sqlite.exec(stmt); } catch { /* column already exists */ }
   }

services/api/src/db/schema.ts

@@ -20,6 +20,7 @@ export const integrationTokens = sqliteTable('integration_tokens', {
   accessToken: text('access_token').notNull(),
   refreshToken: text('refresh_token'),
   expiresAt: text('expires_at'),
+  tokenStatus: text('token_status').notNull().default('active'), // 'active' | 'needs_reconnect'
   connectedAt: text('connected_at').notNull(),
 });
 
@@ -81,6 +82,9 @@ export const tipScores = sqliteTable('tip_scores', {
   candidateCount: integer('candidate_count'),
   latencyMs: integer('latency_ms'),
   servedAt: text('served_at').notNull(),
+  promptVersion: text('prompt_version'),             // e.g. 'v1' — tracks which prompt template generated this tip
+  llmModel: text('llm_model'),                       // e.g. 'tip-generator/qwen2.5:7b' — null for bandit-only tips
+  tipKind: text('tip_kind'),                         // 'task' | 'advice' | 'insight' | 'reminder'
 });
 
 // ── Simulation runs ──────────────────────────────────────────────────────────

services/api/src/routes/__tests__/recommender.test.ts

@@ -0,0 +1,190 @@
+/**
+ * Integration tests for POST /recommend and tip_scores DB writes.
+ * Uses a real in-memory SQLite DB. recommender is imported dynamically
+ * inside beforeAll (same pattern as admin.test.ts) to avoid TDZ issues.
+ * Uses http.request (not fetch) as the test client so that globalThis.fetch
+ * mocking doesn't interfere with the test runner itself.
+ */
+import { describe, it, expect, vi, beforeAll, afterEach } from 'vitest';
+import express from 'express';
+import * as http from 'http';
+import { makeTestDb } from '../../test/db.js';
+import { users, integrationTokens, tipScores } from '../../db/schema.js';
+
+const testDb = makeTestDb();
+
+vi.mock('../../db/index.js', () => ({ db: testDb }));
+vi.mock('../../middleware/session.js', () => ({
+  sessionMiddleware: (_req: express.Request, _res: express.Response, next: express.NextFunction) => next(),
+  requireAuth: (req: express.Request, _res: express.Response, next: express.NextFunction) => {
+    (req as any).userId = 'user-1';
+    next();
+  },
+}));
+vi.mock('../../events/bus.js', () => ({ bus: { publish: vi.fn() } }));
+
+/** Minimal http.request wrapper → { status, body } */
+function post(url: string): Promise<{ status: number; body: any }> {
+  return new Promise((resolve, reject) => {
+    const u = new URL(url);
+    const req = http.request(
+      { hostname: u.hostname, port: Number(u.port), path: u.pathname, method: 'POST',
+        headers: { 'Content-Type': 'application/json' } },
+      (res) => {
+        let data = '';
+        res.on('data', (c) => { data += c; });
+        res.on('end', () => {
+          try { resolve({ status: res.statusCode ?? 0, body: data ? JSON.parse(data) : null }); }
+          catch { resolve({ status: res.statusCode ?? 0, body: data }); }
+        });
+      },
+    );
+    req.on('error', reject);
+    req.end();
+  });
+}
+
+describe('POST /recommend integration', () => {
+  let server: http.Server;
+  let baseUrl: string;
+  let savedFetch: typeof globalThis.fetch;
+  let clearCache: () => void;
+
+  beforeAll(async () => {
+    await testDb.insert(users).values({
+      id: 'user-1', email: 'u@test.com', role: 'user',
+      consentGiven: 1, createdAt: new Date().toISOString(),
+    });
+    await testDb.insert(integrationTokens).values({
+      id: 'tok-1', userId: 'user-1', provider: 'todoist',
+      accessToken: 'fake-token', connectedAt: new Date().toISOString(),
+    });
+
+    const mod = await import('../recommender.js');
+    const { recommenderRouter } = mod;
+    clearCache = (mod as any)._clearTaskCacheForTests;
+    const app = express();
+    app.use(express.json());
+    app.use('/api', recommenderRouter);
+    server = app.listen(0);
+    const addr = server.address() as { port: number };
+    baseUrl = `http://localhost:${addr.port}`;
+    savedFetch = globalThis.fetch;
+  });
+
+  afterEach(() => {
+    globalThis.fetch = savedFetch;
+    clearCache?.();
+  });
+
+  it('returns 204 when Todoist + LLM both return empty', async () => {
+    globalThis.fetch = vi.fn().mockResolvedValue({
+      ok: true, status: 200,
+      json: async () => ({ results: [] }),
+    } as any);
+    const { status } = await post(`${baseUrl}/api/recommend`);
+    expect(status).toBe(204);
+  });
+
+  it('serves todoist tip and writes correct tip_scores columns', async () => {
+    globalThis.fetch = vi.fn().mockImplementation((url: string) => {
+      if (String(url).includes('todoist.com')) {
+        return Promise.resolve({
+          ok: true, status: 200,
+          json: async () => ({
+            results: [{ id: 'task-1', content: 'Write tests', priority: 3, due: { date: '2026-04-10' } }],
+          }),
+        } as any);
+      }
+      if (String(url).includes('/generate')) {
+        return Promise.resolve({ ok: false, status: 503, json: async () => ({}) } as any);
+      }
+      if (String(url).includes('/score')) {
+        return Promise.resolve({
+          ok: true, status: 200,
+          json: async () => ({ tip_id: 'todoist:task-1', score: 0.8 }),
+        } as any);
+      }
+      return Promise.resolve({ ok: false, status: 500, json: async () => ({}) } as any);
+    });
+
+    const { status, body } = await post(`${baseUrl}/api/recommend`);
+    expect(status).toBe(200);
+    expect(body.tip.source).toBe('todoist');
+    expect(body.tip.kind).toBe('task');
+
+    const rows = await testDb.select().from(tipScores);
+    const row = rows[rows.length - 1];
+    expect(row.tipKind).toBe('task');
+    expect(row.promptVersion).toBeNull();
+    expect(row.llmModel).toBeNull();
+  });
+
+  it('writes prompt_version + llm_model when LLM tip is served', async () => {
+    globalThis.fetch = vi.fn().mockImplementation((url: string) => {
+      if (String(url).includes('todoist.com')) {
+        return Promise.resolve({
+          ok: true, status: 200,
+          json: async () => ({ results: [] }),
+        } as any);
+      }
+      if (String(url).includes('/generate')) {
+        return Promise.resolve({
+          ok: true, status: 200,
+          json: async () => ({
+            candidates: [{ id: 'adv-1', content: 'Take a break.', rationale: 'You deserve it.' }],
+            model: 'tip-generator',
+          }),
+        } as any);
+      }
+      if (String(url).includes('/score')) {
+        return Promise.resolve({
+          ok: true, status: 200,
+          json: async () => ({ tip_id: 'llm:adv-1', score: 0.9 }),
+        } as any);
+      }
+      return Promise.resolve({ ok: false, status: 500, json: async () => ({}) } as any);
+    });
+
+    const { status, body } = await post(`${baseUrl}/api/recommend`);
+    expect(status).toBe(200);
+    expect(body.tip.source).toBe('llm');
+    expect(body.tip.kind).toBe('advice');
+    expect(body.tip.rationale).toBe('You deserve it.');
+
+    const rows = await testDb.select().from(tipScores);
+    const row = rows[rows.length - 1];
+    expect(row.promptVersion).toBe('v1');
+    expect(row.llmModel).toBe('tip-generator');
+    expect(row.tipKind).toBe('advice');
+  });
+
+  it('falls back to todoist tip when /generate returns non-200', async () => {
+    globalThis.fetch = vi.fn().mockImplementation((url: string) => {
+      if (String(url).includes('todoist.com')) {
+        return Promise.resolve({
+          ok: true, status: 200,
+          json: async () => ({
+            results: [{ id: 'fallback-1', content: 'Do stuff', priority: 2, due: null }],
+          }),
+        } as any);
+      }
+      if (String(url).includes('/generate')) {
+        return Promise.resolve({ ok: false, status: 502, json: async () => ({}) } as any);
+      }
+      if (String(url).includes('/score')) {
+        return Promise.resolve({
+          ok: true, status: 200,
+          json: async () => ({ tip_id: 'todoist:fallback-1', score: 0.5 }),
+        } as any);
+      }
+      return Promise.resolve({ ok: false, status: 500, json: async () => ({}) } as any);
+    });
+
+    const { status, body } = await post(`${baseUrl}/api/recommend`);
+    expect([200, 204]).toContain(status);
+    if (status === 200) {
+      expect(body.tip.source).toBe('todoist');
+    }
+  });
+});

services/api/src/routes/__tests__/recommender.unit.test.ts

@@ -0,0 +1,39 @@
+/**
+ * Pure-function unit tests for recommender logic — no DB, no HTTP.
+ * These can import directly from the module without any mocking.
+ */
+import { describe, it, expect } from 'vitest';
+import { inferReward, dueAgeDays } from '../recommender.js';
+
+describe('inferReward', () => {
+  it('dismiss → -1', () => expect(inferReward('dismiss', null)).toBe(-1.0));
+  it('snooze → +0.1', () => expect(inferReward('snooze', null)).toBe(0.1));
+  it('helpful → +0.5', () => expect(inferReward('helpful', null)).toBe(0.5));
+  it('not_helpful → -0.5', () => expect(inferReward('not_helpful', null)).toBe(-0.5));
+  it('done with null dwell → +0.5', () => expect(inferReward('done', null)).toBe(0.5));
+  it('done < 15s (reflex) → -0.3', () => expect(inferReward('done', 5_000)).toBe(-0.3));
+  it('done 15s–2min (magic) → +1.0', () => expect(inferReward('done', 60_000)).toBe(1.0));
+  it('done 2–10min (good) → +0.6', () => expect(inferReward('done', 300_000)).toBe(0.6));
+  it('done > 10min (eventual) → +0.3', () => expect(inferReward('done', 700_000)).toBe(0.3));
+  it('done exactly 15s (boundary) → magic zone', () => expect(inferReward('done', 15_000)).toBe(1.0));
+  it('done exactly 2min (boundary) → good zone', () => expect(inferReward('done', 120_000)).toBe(0.6));
+});
+
+describe('dueAgeDays', () => {
+  it('null due → 0', () => expect(dueAgeDays(null)).toBe(0));
+  it('empty object → 0', () => expect(dueAgeDays({})).toBe(0));
+  it('future date → 0 (clamped)', () => {
+    const future = new Date(Date.now() + 86_400_000).toISOString();
+    expect(dueAgeDays({ datetime: future })).toBe(0);
+  });
+  it('past date → positive age', () => {
+    const twoDaysAgo = new Date(Date.now() - 2 * 86_400_000).toISOString();
+    const age = dueAgeDays({ datetime: twoDaysAgo });
+    expect(age).toBeGreaterThan(1.9);
+    expect(age).toBeLessThan(2.1);
+  });
+  it('date-only field used when datetime absent', () => {
+    const yesterday = new Date(Date.now() - 86_400_000).toISOString().slice(0, 10);
+    expect(dueAgeDays({ date: yesterday })).toBeGreaterThan(0);
+  });
+});

services/api/src/routes/integrations.ts

@@ -24,7 +24,7 @@ router.get('/', requireAuth, async (req: AuthenticatedRequest, res: Response) =>
 
   const integrations = tokens.map((t) => ({
     provider: t.provider,
-    status: 'connected',
+    status: t.tokenStatus === 'needs_reconnect' ? 'needs_reconnect' : 'connected',
     connectedAt: t.connectedAt,
   }));
 
@@ -97,6 +97,7 @@ router.get('/todoist/callback', async (req: Request, res: Response) => {
     userId: pending.userId,
     provider: 'todoist',
     accessToken: access_token,
+    tokenStatus: 'active',
     connectedAt: now,
   });
 

services/api/src/routes/recommender.ts

@@ -6,23 +6,15 @@ import { eq, and, desc } from 'drizzle-orm';
 import { requireAuth, AuthenticatedRequest } from '../middleware/session.js';
 import { config } from '../config.js';
 import { bus } from '../events/bus.js';
-import type { Tip } from '@oo/shared-types';
+import type { TipCandidate } from '@oo/shared-types';
 
 const router: ExpressRouter = Router();
 
 const CACHE_TTL_MS = 30_000;
+const PROMPT_VERSION = 'v1';
 
-interface TaskFeatures {
+const taskCache = new Map<string, { tasks: TipCandidate[]; fetchedAt: number }>();
-  is_overdue: boolean;
+export const _clearTaskCacheForTests = () => taskCache.clear();
-  task_age_days: number;
-  priority: number;
-}
-
-interface CachedTask extends Tip {
-  features: TaskFeatures;
-}
-
-const taskCache = new Map<string, { tasks: CachedTask[]; fetchedAt: number }>();
 
 // ---------------------------------------------------------------------------
 // Shadow-policy registry
@@ -49,7 +41,7 @@ export function setPolicyActive(name: string, active: boolean): boolean {
 // Todoist helpers
 // ---------------------------------------------------------------------------
 
-function dueAgeDays(due: { date?: string; datetime?: string } | null | undefined): number {
+export function dueAgeDays(due: { date?: string; datetime?: string } | null | undefined): number {
   if (!due) return 0;
   const dateStr = due.datetime ?? due.date;
   if (!dateStr) return 0;
@@ -57,7 +49,7 @@ function dueAgeDays(due: { date?: string; datetime?: string } | null | undefined
   return Math.max(0, (Date.now() - dueMs) / (1000 * 60 * 60 * 24));
 }
 
-async function fetchTodoistTasks(userId: string, accessToken: string): Promise<CachedTask[]> {
+async function fetchTodoistTasks(userId: string, accessToken: string): Promise<TipCandidate[]> {
   const cached = taskCache.get(userId);
   if (cached && Date.now() - cached.fetchedAt < CACHE_TTL_MS) return cached.tasks;
 
@@ -73,6 +65,10 @@ async function fetchTodoistTasks(userId: string, accessToken: string): Promise<C
         provider: 'todoist',
         detectedAt: new Date().toISOString(),
       });
+      await db
+        .update(integrationTokens)
+        .set({ tokenStatus: 'needs_reconnect' })
+        .where(and(eq(integrationTokens.userId, userId), eq(integrationTokens.provider, 'todoist')));
     }
     return cached?.tasks ?? [];
   }
@@ -87,13 +83,14 @@ async function fetchTodoistTasks(userId: string, accessToken: string): Promise<C
   };
 
   const now = new Date();
-  const tasks: CachedTask[] = (body.results ?? []).map((t) => {
+  const tasks: TipCandidate[] = (body.results ?? []).map((t) => {
     const ageDays = dueAgeDays(t.due);
     const isOverdue = ageDays > 0;
     return {
       id: `todoist:${t.id}`,
       content: t.content,
       source: 'todoist' as const,
+      kind: 'task' as const,
       sourceId: t.id,
       createdAt: now.toISOString(),
       features: {
@@ -111,10 +108,14 @@ async function fetchTodoistTasks(userId: string, accessToken: string): Promise<C
   return tasks;
 }
 
+// ---------------------------------------------------------------------------
+// Stage 2: score candidates via ml/serving bandit
+// ---------------------------------------------------------------------------
+
 /** Call ml/serving for scored selection; returns { tip_id, score } or null on failure */
 async function remotePolicy(
   userId: string,
-  tasks: CachedTask[],
+  tasks: TipCandidate[],
 ): Promise<{ tipId: string; score: number; policy: string } | null> {
   const hour = new Date().getHours();
   const dayOfWeek = new Date().getDay();
@@ -147,13 +148,64 @@ async function remotePolicy(
   }
 }
 
-function randomPolicy(candidates: CachedTask[]): CachedTask | null {
+function randomPolicy(candidates: TipCandidate[]): TipCandidate | null {
   if (!candidates.length) return null;
   return candidates[Math.floor(Math.random() * candidates.length)];
 }
 
+// ---------------------------------------------------------------------------
+// Stage 1b: fetch LLM candidates from ml/serving /generate
+// ---------------------------------------------------------------------------
+
+interface LlmCandidate {
+  id: string;
+  content: string;
+  rationale?: string;
+}
+
+async function fetchLlmCandidates(
+  userId: string,
+  todoistTasks: TipCandidate[],
+  hour: number,
+  dayOfWeek: number,
+): Promise<TipCandidate[]> {
+  try {
+    const tasks = todoistTasks.slice(0, 10).map((t) => ({
+      content: t.content,
+      priority: t.features.priority,
+      is_overdue: t.features.is_overdue,
+      task_age_days: t.features.task_age_days,
+    }));
+    const res = await fetch(`${config.ML_SERVING_URL}/generate`, {
+      method: 'POST',
+      headers: { 'Content-Type': 'application/json' },
+      body: JSON.stringify({
+        user_id: userId,
+        context: { tasks, hour_of_day: hour, day_of_week: dayOfWeek },
+        n: 3,
+      }),
+      signal: AbortSignal.timeout(15_000),
+    });
+    if (!res.ok) return [];
+    const data = (await res.json()) as { candidates: LlmCandidate[]; model?: string };
+    const now = new Date().toISOString();
+    return data.candidates.map((c) => ({
+      id: `llm:${c.id}`,
+      content: c.content,
+      source: 'llm' as const,
+      kind: 'advice' as const,
+      rationale: c.rationale,
+      createdAt: now,
+      features: { is_overdue: false, task_age_days: 0, priority: 1 },
+    }));
+  } catch {
+    return [];
+  }
+}
+
 // ---------------------------------------------------------------------------
 // POST /api/recommend
+// Pipeline: [Stage 1] assemble candidates → [Stage 2] score → [Stage 3] serve
 // ---------------------------------------------------------------------------
 router.post('/recommend', requireAuth, async (req: AuthenticatedRequest, res: Response) => {
   const [token] = await db
@@ -167,34 +219,42 @@ router.post('/recommend', requireAuth, async (req: AuthenticatedRequest, res: Re
     return;
   }
 
-  const tasks = await fetchTodoistTasks(req.userId!, token.accessToken);
+  const hour = new Date().getHours();
-  if (!tasks.length) {
+  const dayOfWeek = new Date().getDay();
+
+  // Stage 1: assemble candidates — Todoist tasks + LLM-generated advice (parallel)
+  const [todoistTasks, llmCandidates] = await Promise.all([
+    fetchTodoistTasks(req.userId!, token.accessToken),
+    fetchLlmCandidates(req.userId!, taskCache.get(req.userId!)?.tasks ?? [], hour, dayOfWeek),
+  ]);
+
+  const allCandidates: TipCandidate[] = [...todoistTasks, ...llmCandidates];
+  if (!allCandidates.length) {
     res.status(204).end();
     return;
   }
 
-  const hour = new Date().getHours();
-  const dayOfWeek = new Date().getDay();
   const t0 = Date.now();
 
-  // RemotePolicy with RandomPolicy fallback
+  // Stage 2: score — egreedy bandit with random fallback
-  const scored = await remotePolicy(req.userId!, tasks);
+  const scored = await remotePolicy(req.userId!, allCandidates);
   const latencyMs = Date.now() - t0;
   const tip = scored
-    ? (tasks.find((t) => t.id === scored.tipId) ?? randomPolicy(tasks))
+    ? (allCandidates.find((t) => t.id === scored.tipId) ?? randomPolicy(allCandidates))
-    : randomPolicy(tasks);
+    : randomPolicy(allCandidates);
 
   if (!tip) {
     res.status(204).end();
     return;
   }
 
+  // Stage 3: serve + log
   const policy = scored ? scored.policy : 'random';
+  const isLlmTip = tip.source === 'llm';
   const servedAt = new Date().toISOString();
 
   await db.insert(tipViews).values({ id: nanoid(), userId: req.userId!, tipId: tip.id, servedAt });
 
-  // Log recommendation explainability
   await db.insert(tipScores).values({
     id: nanoid(),
     userId: req.userId!,
@@ -208,9 +268,12 @@ router.post('/recommend', requireAuth, async (req: AuthenticatedRequest, res: Re
       hour_of_day: hour,
       day_of_week: dayOfWeek,
     }),
-    candidateCount: tasks.length,
+    candidateCount: allCandidates.length,
     latencyMs,
     servedAt,
+    promptVersion: isLlmTip ? PROMPT_VERSION : null,
+    llmModel: isLlmTip ? 'tip-generator' : null,
+    tipKind: tip.kind ?? null,
   });
 
   bus.publish('signals.tip.served', {
@@ -224,7 +287,7 @@ router.post('/recommend', requireAuth, async (req: AuthenticatedRequest, res: Re
   for (const [name, s] of shadowPolicies) {
     if (!s.active) continue;
     if (name.startsWith('random')) {
-      const shadowTip = randomPolicy(tasks);
+      const shadowTip = randomPolicy(allCandidates);
       bus.publish('signals.tip.served', {
         userId: req.userId!,
         tipId: shadowTip?.id ?? 'none',
@@ -249,7 +312,7 @@ router.post('/recommend', requireAuth, async (req: AuthenticatedRequest, res: Re
 //   done 2 – 10 min      → +0.6 (good: user engaged, acted in same session)
 //   done > 10 min        → +0.3 (eventually done; tip may have helped, unclear)
 // ---------------------------------------------------------------------------
-function inferReward(action: string, dwellMs: number | null): number {
+export function inferReward(action: string, dwellMs: number | null): number {
   if (action === 'dismiss')     return -1.0;
   if (action === 'snooze')      return 0.1;
   if (action === 'helpful')     return 0.5;
@@ -269,7 +332,7 @@ async function sendRewardWithRetry(
   userId: string,
   tipId: string,
   reward: number,
-  features: TaskFeatures,
+  features: TipCandidate['features'],
 ): Promise<void> {
   const body = JSON.stringify({
     user_id: userId,
@@ -347,7 +410,7 @@ router.post('/tip/:id/feedback', requireAuth, async (req: AuthenticatedRequest,
     createdAt: now.toISOString(),
   });
 
-  const task = taskCache.get(req.userId!)?.tasks.find((t) => t.id === tipId);
+  const task: TipCandidate | undefined = taskCache.get(req.userId!)?.tasks.find((t) => t.id === tipId);
 
   taskCache.delete(req.userId!);
 

services/api/src/test/db.ts

@@ -32,6 +32,7 @@ export function makeTestDb() {
       refresh_token TEXT,
       expires_at TEXT,
       connected_at TEXT NOT NULL,
+      token_status TEXT NOT NULL DEFAULT 'active',
       UNIQUE(user_id, provider)
     );
 
@@ -88,7 +89,10 @@ export function makeTestDb() {
       features_json TEXT,
       candidate_count INTEGER,
       latency_ms INTEGER,
-      served_at TEXT NOT NULL
+      served_at TEXT NOT NULL,
+      prompt_version TEXT,
+      llm_model TEXT,
+      tip_kind TEXT
     );
 
     CREATE TABLE IF NOT EXISTS saved_queries (

services/api/vitest.config.ts

@@ -4,6 +4,13 @@ export default defineConfig({
   test: {
     globals: true,
     environment: 'node',
+    env: {
+      SESSION_SECRET: 'test-secret',
+      GOOGLE_CLIENT_ID: 'test-google-id',
+      GOOGLE_CLIENT_SECRET: 'test-google-secret',
+      TODOIST_CLIENT_ID: 'test-todoist-id',
+      TODOIST_CLIENT_SECRET: 'test-todoist-secret',
+    },
     coverage: {
       provider: 'v8',
       reporter: ['text', 'lcov'],