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api/alembic/versions/009_cloud_scout_gmail_address.py

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+"""Add gmail_address to cloud_scout_configs.
+
+Revision ID: 009
+Revises: 008
+Create Date: 2026-05-16
+"""
+
+from typing import Sequence, Union
+
+import sqlalchemy as sa
+from alembic import op
+
+
+revision: str = "009"
+down_revision: Union[str, None] = "008"
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    op.add_column("cloud_scout_configs", sa.Column("gmail_address", sa.String(320), nullable=True))
+
+
+def downgrade() -> None:
+    op.drop_column("cloud_scout_configs", "gmail_address")

api/app/api/routes/scout_webhooks.py

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+"""Gmail Pub/Sub push receiver.
+
+Google Pub/Sub push subscriptions deliver Gmail watch notifications as POST
+requests with a JSON envelope. The body payload contains a base64-encoded
+JSON blob with ``emailAddress`` + ``historyId``. We resolve the user by
+email, look up their cloud_scout_configs row for provider='gmail', and
+hand off to ScoutEngine.trigger_scout.
+
+Authentication: Pub/Sub push includes an OIDC JWT in the Authorization
+header. We verify it against Google's public keys with the audience
+configured in our Pub/Sub subscription.
+
+Dev mode: when ``GMAIL_PUBSUB_AUDIENCE`` is empty, JWT verification is
+skipped and a warning is logged. Production must set this env var.
+"""
+
+from __future__ import annotations
+
+import base64
+import json
+import logging
+import uuid
+
+from fastapi import APIRouter, Header, HTTPException, Request, status
+from sqlalchemy import select
+
+from app.config.settings import settings
+from app.db import async_session
+from app.models import CloudScoutConfig, User
+from app.scouts.engine import ScoutEngine
+
+logger = logging.getLogger(__name__)
+router = APIRouter(prefix="/scouts/webhooks", tags=["scout-webhooks"])
+
+
+def _verify_pubsub_jwt(token: str) -> bool:
+    """Verify the Google Pub/Sub OIDC JWT.
+
+    Returns True when valid, False on any verification failure.
+
+    Dev skip: if ``settings.GMAIL_PUBSUB_AUDIENCE`` is empty, logs a
+    warning and returns True so local development works without a real
+    Pub/Sub subscription. Production must configure the audience.
+    """
+    if not token:
+        return False
+
+    if not settings.GMAIL_PUBSUB_AUDIENCE:
+        logger.warning(
+            "GMAIL_PUBSUB_AUDIENCE not set — skipping Pub/Sub JWT verification (dev mode only)"
+        )
+        return True
+
+    try:
+        from google.auth.transport import requests as g_requests  # noqa: PLC0415
+        from google.oauth2 import id_token  # noqa: PLC0415
+
+        id_token.verify_oauth2_token(
+            token,
+            g_requests.Request(),
+            audience=settings.GMAIL_PUBSUB_AUDIENCE,
+        )
+        return True
+    except Exception:
+        logger.warning("pubsub jwt verification failed", exc_info=True)
+        return False
+
+
+@router.post("/gmail", status_code=status.HTTP_204_NO_CONTENT)
+async def gmail_pubsub(
+    request: Request,
+    authorization: str = Header(default=""),
+) -> None:
+    """Receive a Gmail Pub/Sub push notification.
+
+    Verifies the OIDC JWT, decodes the Pub/Sub envelope, resolves the user
+    by email, and triggers ScoutEngine.trigger_scout for each enabled Gmail
+    scout belonging to that user.
+
+    Returns 204 No Content on success (including benign no-ops like unknown
+    email or empty message data). Returns 401 on JWT verification failure.
+    """
+    token = authorization.removeprefix("Bearer ").strip()
+    if not _verify_pubsub_jwt(token):
+        raise HTTPException(status.HTTP_401_UNAUTHORIZED, "Invalid Pub/Sub JWT")
+
+    body = await request.json()
+    msg = body.get("message") or {}
+    raw = msg.get("data")
+    if not raw:
+        return  # ack without action — empty message data
+
+    try:
+        decoded = json.loads(base64.b64decode(raw).decode())
+    except Exception:
+        logger.warning("pubsub payload decode failed")
+        return
+
+    email = decoded.get("emailAddress")
+    if not email:
+        return
+
+    async with async_session() as session:
+        user_q = await session.execute(select(User).where(User.email == email))
+        user = user_q.scalar_one_or_none()
+        if user is None:
+            logger.info("pubsub: no user for %s — ignoring", email)
+            return
+        scouts_q = await session.execute(
+            select(CloudScoutConfig).where(
+                CloudScoutConfig.user_id == user.id,
+                CloudScoutConfig.provider == "gmail",
+                CloudScoutConfig.enabled == True,  # noqa: E712
+            )
+        )
+        scouts = scouts_q.scalars().all()
+
+    engine = ScoutEngine()
+    for scout in scouts:
+        await engine.trigger_scout(uuid.UUID(str(scout.id)))

api/app/api/routes/scouts.py

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+"""Scout routes.
+
+Backend responsibilities are intentionally minimal:
+    GET  /scouts/catalog         — static catalog for UI display
+    POST /scouts/can-create      — billing eligibility check
+    POST /scouts/trigger         — trigger a local scout run
+
+Scout configuration is owned by the Electron app and is not persisted
+in backend scout-config tables.
+
+Gmail OAuth setup (scout-specific consent):
+    GET  /scouts/oauth/gmail/authorize       — returns consent-screen URL
+    GET  /scouts/oauth/gmail/web-callback    — bounces to deep link (excluded from schema)
+    POST /scouts/oauth/gmail/callback        — exchanges code, stores encrypted token
+"""
+
+from __future__ import annotations
+
+import asyncio
+import logging
+import secrets
+import time
+import urllib.parse
+import uuid
+from datetime import datetime, timezone
+
+from fastapi import APIRouter, Depends, HTTPException, status
+from fastapi.responses import RedirectResponse
+from sqlalchemy import delete as sa_delete, func, select
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from pydantic import BaseModel
+
+from app.api.deps import get_current_user
+from app.auth.oauth_providers import generate_pkce_pair
+from app.billing.tier_manager import FEATURES
+from app.config.settings import settings
+from app.core.scout_runner import is_agent_running, run_local_agent
+from app.core.device_manager import device_manager
+from app.core.note_summarizer import generate_note_summary
+from app.db import get_session
+from app.integrations import decrypt_token, encrypt_token
+from app.models import CloudScoutConfig, ScoutRunLog, LocalScoutConfig
+from app.scouts.connectors.registry import get_connector
+from app.schemas import (
+    CloudScoutCreateRequest,
+    CloudScoutResponse,
+    CloudScoutUpdateRequest,
+    ScoutCatalogItem,
+    ScoutCreationCheckRequest,
+    ScoutCreationCheckResponse,
+    ScoutRunLogResponse,
+    ScoutTriggerRequest,
+    UserProfile,
+)
+
+logger = logging.getLogger(__name__)
+
+router = APIRouter(prefix="/scouts", tags=["scouts"])
+
+
+# ── Datetime helpers ──────────────────────────────────────────────────
+
+def _dt_ms(dt: datetime) -> int:
+    return int(dt.timestamp() * 1000)
+
+
+def _dt_ms_opt(dt: datetime | None) -> int | None:
+    return int(dt.timestamp() * 1000) if dt else None
+
+
+def _to_data_types(values: list[str]) -> list[str]:
+    normalize = {
+        "task": "tasks",           "tasks": "tasks",
+        "note": "notes",           "notes": "notes",
+        "timeline": "timelines",   "timelines": "timelines",   "timelineEvents": "timelines",
+        "project": "projects",     "projects": "projects",
+    }
+    seen: set[str] = set()
+    result: list[str] = []
+    for v in values:
+        mapped = normalize.get(v)
+        if mapped and mapped not in seen:
+            seen.add(mapped)
+            result.append(mapped)
+    return result
+
+
+def _to_run_log_response(log: ScoutRunLog) -> ScoutRunLogResponse:
+    return ScoutRunLogResponse(
+        id=log.id,
+        agent_id=log.scout_id,
+        agent_type=log.scout_type,  # type: ignore[arg-type]
+        status=log.status,  # type: ignore[arg-type]
+        items_processed=log.items_processed,
+        items_created=log.items_created,
+        errors=log.errors or [],
+        started_at=_dt_ms(log.started_at),
+        completed_at=_dt_ms_opt(log.completed_at),
+    )
+
+
+def _enforce_agent_limit(tier: str, current_count: int) -> int:
+    limit: int = FEATURES.get(tier, FEATURES["free"])["batch_active"]
+    if limit != -1 and current_count >= limit:
+        raise HTTPException(
+            status_code=status.HTTP_403_FORBIDDEN,
+            detail=f"Agent limit ({limit}) reached for your tier. Upgrade to create more.",
+        )
+    return limit
+
+
+async def _enforce_run_frequency(
+    tier: str,
+    user_id: str,
+    db: AsyncSession,
+) -> None:
+    """Raise HTTP 402 if the user has exceeded their daily batch run limit."""
+    limit: int = FEATURES.get(tier, FEATURES["free"])["batch_runs_per_day"]
+    if limit == -1:
+        return  # unlimited
+
+    today_start = datetime.now(timezone.utc).replace(
+        hour=0, minute=0, second=0, microsecond=0
+    )
+    result = await db.execute(
+        select(func.count(ScoutRunLog.id)).where(
+            ScoutRunLog.user_id == user_id,
+            ScoutRunLog.started_at >= today_start,
+        )
+    )
+    runs_today: int = result.scalar_one()
+
+    if runs_today >= limit:
+        raise HTTPException(
+            status_code=status.HTTP_402_PAYMENT_REQUIRED,
+            detail=f"Daily batch run limit ({limit}) reached for your tier. Upgrade for more runs.",
+        )
+
+
+# ── Catalog ───────────────────────────────────────────────────────────
+
+@router.get("/catalog", response_model=list[ScoutCatalogItem])
+async def get_agent_catalog(
+    current_user: UserProfile = Depends(get_current_user),
+) -> list[ScoutCatalogItem]:
+    """Return the static list of available agent types and their descriptions."""
+    return [
+        ScoutCatalogItem(
+            type="local_directory",
+            name="Local Directory Monitor",
+            description="Watches local directories, extracts data from files using AI",
+        ),
+        ScoutCatalogItem(
+            type="gmail",
+            name="Gmail Connector",
+            description="Scans Gmail inbox, extracts tasks/notes from emails",
+        ),
+        ScoutCatalogItem(
+            type="teams",
+            name="Microsoft Teams Connector",
+            description="Monitors Teams messages, extracts action items",
+        ),
+        ScoutCatalogItem(
+            type="outlook",
+            name="Outlook Connector",
+            description="Scans Outlook inbox, extracts tasks/notes",
+        ),
+    ]
+
+
+@router.post("/can-create", response_model=ScoutCreationCheckResponse)
+async def can_create_agent(
+    body: ScoutCreationCheckRequest,
+    current_user: UserProfile = Depends(get_current_user),
+) -> ScoutCreationCheckResponse:
+    """Check if the user can create one more agent based on billing tier.
+
+    Since configuration is client-owned, the Electron app sends its current
+    active agent count and the backend applies tier limits.
+    """
+    limit: int = FEATURES.get(current_user.tier, FEATURES["free"])["batch_active"]
+    allowed = limit == -1 or body.active_agents < limit
+    return ScoutCreationCheckResponse(
+        allowed=allowed,
+        tier=current_user.tier,
+        active_agents=body.active_agents,
+        limit=limit,
+    )
+
+
+@router.post("/trigger", response_model=ScoutRunLogResponse, status_code=status.HTTP_202_ACCEPTED)
+async def trigger_agent_run(
+    body: ScoutTriggerRequest,
+    current_user: UserProfile = Depends(get_current_user),
+    db: AsyncSession = Depends(get_session),
+) -> ScoutRunLogResponse:
+    """Trigger a local agent run using client-provided configuration."""
+    _enforce_agent_limit(current_user.tier, body.active_agents)
+    await _enforce_run_frequency(current_user.tier, current_user.id, db)
+
+    last_run_dt = (
+        datetime.fromtimestamp(body.last_run_at / 1000, tz=timezone.utc)
+        if body.last_run_at
+        else None
+    )
+    config = LocalScoutConfig(
+        id=str(uuid.uuid4()),
+        user_id=current_user.id,
+        device_id=body.device_id,
+        name="Local Directory Monitor",
+        directory_paths=[body.directory],
+        data_types=_to_data_types(body.what_to_extract),
+        prompt_template=body.custom_agent_prompt or "",
+        scout_config=body.agent_config,
+        file_extensions=[],
+        schedule_cron=body.batch_interval,
+        enabled=True,
+        last_run_at=last_run_dt,
+    )
+
+    # Use the FE's stable agent_id if provided, fall back to the ephemeral config id.
+    stable_agent_id = body.agent_id or config.id
+
+    if is_agent_running(stable_agent_id):
+        raise HTTPException(
+            status_code=status.HTTP_409_CONFLICT,
+            detail="Agent is already running. Only one run per agent is allowed at a time.",
+        )
+
+    run_log = ScoutRunLog(
+        scout_id=stable_agent_id,
+        scout_type="local",
+        user_id=current_user.id,
+        status="running",
+    )
+    db.add(run_log)
+    await db.commit()
+    await db.refresh(run_log)
+
+    run_context = {
+        "type": "agent_batch",
+        "run_id": run_log.id,
+        "agent_id": stable_agent_id,
+    }
+
+    asyncio.create_task(
+        run_local_agent(current_user.id, config, run_log, device_manager, run_context)
+    )
+
+    return _to_run_log_response(run_log)
+
+
+# ── Note summary endpoint ──────────────────────────────────────────────────────
+
+
+class NoteSummarizeRequest(BaseModel):
+    title: str
+    content: str
+
+
+class NoteSummarizeResponse(BaseModel):
+    summary: str
+
+
+@router.post("/notes/summarize", response_model=NoteSummarizeResponse)
+async def summarize_note(
+    body: NoteSummarizeRequest,
+    current_user: UserProfile = Depends(get_current_user),
+) -> NoteSummarizeResponse:
+    """Generate an AI summary for a note.  Used by the Electron backfill on startup."""
+    summary = await generate_note_summary(body.title, body.content)
+    return NoteSummarizeResponse(summary=summary)
+
+
+# ── Cloud scout CRUD ──────────────────────────────────────────────────────────
+
+_DEFAULT_CLOUD_SCHEDULE = "0 */6 * * *"
+
+
+def _to_cloud_response(scout: CloudScoutConfig) -> dict:
+    return {
+        "id": scout.id,
+        "user_id": scout.user_id,
+        "provider": scout.provider,
+        "name": scout.name,
+        "data_types": scout.data_types or [],
+        "prompt_template": scout.prompt_template or "",
+        "schedule_cron": scout.schedule_cron,
+        "filter_config": scout.filter_config,
+        "auto_trash_spam": scout.auto_trash_spam,
+        "enabled": scout.enabled,
+        "last_run_at": _dt_ms_opt(scout.last_run_at),
+        "gmail_address": scout.gmail_address,
+        "oauth_connected": scout.oauth_token_encrypted is not None,
+        "created_at": _dt_ms(scout.created_at),
+        "updated_at": _dt_ms(scout.updated_at),
+    }
+
+
+@router.get("/cloud", response_model=list[CloudScoutResponse])
+async def list_cloud_scouts(
+    db: AsyncSession = Depends(get_session),
+    current_user: UserProfile = Depends(get_current_user),
+):
+    rows = (await db.execute(
+        select(CloudScoutConfig).where(CloudScoutConfig.user_id == current_user.id)
+    )).scalars().all()
+    return [_to_cloud_response(s) for s in rows]
+
+
+@router.post("/cloud", response_model=CloudScoutResponse, status_code=status.HTTP_201_CREATED)
+async def create_cloud_scout(
+    body: CloudScoutCreateRequest,
+    db: AsyncSession = Depends(get_session),
+    current_user: UserProfile = Depends(get_current_user),
+):
+    scout = CloudScoutConfig(
+        id=str(uuid.uuid4()),
+        user_id=current_user.id,
+        provider=body.provider,
+        name=body.name,
+        data_types=body.data_types,
+        prompt_template=body.prompt_template,
+        filter_config=body.filter_config,
+        schedule_cron=body.schedule_cron or _DEFAULT_CLOUD_SCHEDULE,
+        auto_trash_spam=body.auto_trash_spam,
+        enabled=True,
+    )
+    db.add(scout)
+    await db.commit()
+    await db.refresh(scout)
+    return _to_cloud_response(scout)
+
+
+@router.put("/cloud/{scout_id}", response_model=CloudScoutResponse)
+async def update_cloud_scout(
+    scout_id: str,
+    body: CloudScoutUpdateRequest,
+    db: AsyncSession = Depends(get_session),
+    current_user: UserProfile = Depends(get_current_user),
+):
+    scout = await db.get(CloudScoutConfig, scout_id)
+    if scout is None or scout.user_id != current_user.id:
+        raise HTTPException(status.HTTP_404_NOT_FOUND, "Scout not found")
+    if body.name is not None:
+        scout.name = body.name
+    if body.data_types is not None:
+        scout.data_types = body.data_types
+    if body.prompt_template is not None:
+        scout.prompt_template = body.prompt_template
+    if body.schedule_cron is not None:
+        scout.schedule_cron = body.schedule_cron
+    if body.filter_config is not None:
+        scout.filter_config = body.filter_config
+    if body.auto_trash_spam is not None:
+        scout.auto_trash_spam = body.auto_trash_spam
+    if body.enabled is not None:
+        scout.enabled = body.enabled
+    await db.commit()
+    await db.refresh(scout)
+    return _to_cloud_response(scout)
+
+
+@router.delete("/cloud/{scout_id}")
+async def delete_cloud_scout(
+    scout_id: str,
+    db: AsyncSession = Depends(get_session),
+    current_user: UserProfile = Depends(get_current_user),
+):
+    scout = await db.get(CloudScoutConfig, scout_id)
+    if scout is None or scout.user_id != current_user.id:
+        raise HTTPException(status.HTTP_404_NOT_FOUND, "Scout not found")
+    # Core deletes bypass the polymorphic ScoutRunLog relationship whose
+    # varchar scout_id vs uuid id join is not directly comparable in Postgres.
+    # scout_run_logs.scout_id is a plain string (matches the str scout_id);
+    # scout_triage_queue rows cascade automatically via their FK ondelete.
+    await db.execute(sa_delete(ScoutRunLog).where(ScoutRunLog.scout_id == scout_id))
+    await db.execute(sa_delete(CloudScoutConfig).where(CloudScoutConfig.id == scout_id))
+    await db.commit()
+    return {"ok": True}
+
+
+@router.get("/cloud/{scout_id}/gmail-labels")
+async def list_gmail_labels(
+    scout_id: str,
+    db: AsyncSession = Depends(get_session),
+    current_user: UserProfile = Depends(get_current_user),
+):
+    scout = await db.get(CloudScoutConfig, scout_id)
+    if scout is None or scout.user_id != current_user.id:
+        raise HTTPException(status.HTTP_404_NOT_FOUND, "Scout not found")
+    try:
+        connector = get_connector("gmail")
+    except KeyError:
+        return []
+    return await connector.list_labels(scout)
+
+
+@router.post("/cloud/{scout_id}/gmail-disconnect", response_model=CloudScoutResponse)
+async def disconnect_gmail(
+    scout_id: str,
+    db: AsyncSession = Depends(get_session),
+    current_user: UserProfile = Depends(get_current_user),
+):
+    scout = await db.get(CloudScoutConfig, scout_id)
+    if scout is None or scout.user_id != current_user.id:
+        raise HTTPException(status.HTTP_404_NOT_FOUND, "Scout not found")
+    try:
+        connector = get_connector("gmail")
+        await connector.stop_watch(scout)
+    except KeyError:
+        pass
+    scout.oauth_token_encrypted = None
+    scout.gmail_history_id = None
+    scout.gmail_watch_expires_at = None
+    scout.gmail_address = None
+    scout.enabled = False
+    await db.commit()
+    await db.refresh(scout)
+    return _to_cloud_response(scout)
+
+
+# ── Gmail OAuth setup (scout-specific) ───────────────────────────────────────
+
+# Scopes required for Gmail scout connectivity.
+_GMAIL_SCOUT_SCOPES = [
+    "openid",
+    "email",
+    "https://www.googleapis.com/auth/gmail.readonly",
+    "https://www.googleapis.com/auth/gmail.modify",
+]
+
+# Google OAuth endpoints.
+_GOOGLE_AUTH_URL = "https://accounts.google.com/o/oauth2/v2/auth"
+_GOOGLE_TOKEN_URL = "https://oauth2.googleapis.com/token"
+
+# In-memory pending OAuth states for scout Gmail consent.
+#
+# state → {
+#   "code_verifier": str,
+#   "user_id": str,
+#   "expires_at": float (epoch seconds),
+#   "mode": "reconnect" | "create",
+#   "scout_id": str | None,            # set for reconnect mode
+#   "draft": {name, prompt_template, auto_trash_spam} | None,  # set for create mode
+#   "token_encrypted": str | None,     # populated after a successful create-mode callback
+#   "gmail_address": str | None,
+# }
+#
+# Zero-trust: in create mode the encrypted Gmail token lives ONLY here, in
+# process memory, for at most _SCOUT_OAUTH_TTL_SECONDS. It is persisted to the
+# DB only when the user finalizes the scout (POST /scouts/cloud/finalize).
+# An abandoned/errored flow leaves no scout row and no stored token.
+#
+# Production note: this in-memory store is single-process only — replace with
+# Redis (keyed by state, TTL'd) for multi-worker deployments.
+_pending_scout_oauth_states: dict[str, dict] = {}
+_SCOUT_OAUTH_TTL_SECONDS = 900  # 15 minutes
+
+
+def _purge_expired_oauth_states() -> None:
+    now = time.time()
+    expired = [s for s, e in _pending_scout_oauth_states.items() if e.get("expires_at", 0) < now]
+    for s in expired:
+        del _pending_scout_oauth_states[s]
+
+
+def _scout_gmail_redirect_uri() -> str:
+    """Derive the scout Gmail web-callback URI from the configured base OAUTH_REDIRECT_URI.
+
+    ``OAUTH_REDIRECT_URI`` is the full path used for login OAuth
+    (e.g. http://localhost:8000/api/v1/auth/oauth/google/web-callback).
+    We strip the path to get the scheme+host base, then append the scout path.
+    """
+    parsed = urllib.parse.urlparse(settings.OAUTH_REDIRECT_URI)
+    base = f"{parsed.scheme}://{parsed.netloc}"
+    return f"{base}/api/v1/scouts/oauth/gmail/web-callback"
+
+
+class _ScoutGmailAuthorizeResponse(BaseModel):
+    authorize_url: str
+
+
+class _ScoutGmailCallbackBody(BaseModel):
+    code: str
+    state: str
+
+
+class _ScoutGmailAuthorizeDraftBody(BaseModel):
+    name: str
+    prompt_template: str = ""
+    auto_trash_spam: bool = False
+
+
+class _ScoutGmailFinalizeBody(BaseModel):
+    session: str
+    filter_config: dict | None = None
+
+
+def _build_gmail_authorize_url(state: str, code_challenge: str) -> str:
+    """Build the Google consent URL for the scout Gmail flow (shared by both modes)."""
+    redirect_uri = _scout_gmail_redirect_uri()
+    params = {
+        "client_id": settings.GOOGLE_AUTH_CLIENT_ID,
+        "redirect_uri": redirect_uri,
+        "response_type": "code",
+        "scope": " ".join(_GMAIL_SCOUT_SCOPES),
+        "state": state,
+        "code_challenge": code_challenge,
+        "code_challenge_method": "S256",
+        "access_type": "offline",
+        "prompt": "consent",
+    }
+    return f"{_GOOGLE_AUTH_URL}?{urllib.parse.urlencode(params)}"
+
+
+@router.get("/oauth/gmail/authorize", response_model=_ScoutGmailAuthorizeResponse)
+async def scout_gmail_oauth_authorize(
+    scout_id: str,
+    current_user: UserProfile = Depends(get_current_user),
+) -> _ScoutGmailAuthorizeResponse:
+    """Start the Gmail OAuth flow for a specific cloud scout.
+
+    Returns the Google consent-screen URL.  The client opens this URL in the
+    system browser; after consent Google redirects to web-callback which bounces
+    to the ``adiuvai://scout/oauth/gmail/callback`` deep link.
+    """
+    if not settings.GOOGLE_AUTH_CLIENT_ID or not settings.GOOGLE_AUTH_CLIENT_SECRET:
+        raise HTTPException(
+            status.HTTP_503_SERVICE_UNAVAILABLE,
+            "Google OAuth is not configured on this server",
+        )
+
+    code_verifier, code_challenge = generate_pkce_pair()
+    state = secrets.token_urlsafe(32)
+
+    _purge_expired_oauth_states()
+
+    _pending_scout_oauth_states[state] = {
+        "code_verifier": code_verifier,
+        "user_id": current_user.id,
+        "expires_at": time.time() + _SCOUT_OAUTH_TTL_SECONDS,
+        "mode": "reconnect",
+        "scout_id": scout_id,
+        "draft": None,
+        "token_encrypted": None,
+        "gmail_address": None,
+    }
+
+    return _ScoutGmailAuthorizeResponse(
+        authorize_url=_build_gmail_authorize_url(state, code_challenge)
+    )
+
+
+@router.post("/oauth/gmail/authorize-draft", response_model=_ScoutGmailAuthorizeResponse)
+async def scout_gmail_oauth_authorize_draft(
+    body: _ScoutGmailAuthorizeDraftBody,
+    current_user: UserProfile = Depends(get_current_user),
+) -> _ScoutGmailAuthorizeResponse:
+    """Start the Gmail OAuth flow in *creation* mode — no scout row exists yet.
+
+    The draft scout fields are held in the pending OAuth session; the scout is
+    only created once the user finalizes (POST /scouts/cloud/finalize).
+    """
+    if not settings.GOOGLE_AUTH_CLIENT_ID or not settings.GOOGLE_AUTH_CLIENT_SECRET:
+        raise HTTPException(
+            status.HTTP_503_SERVICE_UNAVAILABLE,
+            "Google OAuth is not configured on this server",
+        )
+
+    code_verifier, code_challenge = generate_pkce_pair()
+    state = secrets.token_urlsafe(32)
+
+    _purge_expired_oauth_states()
+
+    _pending_scout_oauth_states[state] = {
+        "code_verifier": code_verifier,
+        "user_id": current_user.id,
+        "expires_at": time.time() + _SCOUT_OAUTH_TTL_SECONDS,
+        "mode": "create",
+        "scout_id": None,
+        "draft": {
+            "name": body.name,
+            "prompt_template": body.prompt_template,
+            "auto_trash_spam": body.auto_trash_spam,
+        },
+        "token_encrypted": None,
+        "gmail_address": None,
+    }
+
+    return _ScoutGmailAuthorizeResponse(
+        authorize_url=_build_gmail_authorize_url(state, code_challenge)
+    )
+
+
+@router.get("/oauth/gmail/web-callback", include_in_schema=False)
+async def scout_gmail_oauth_web_callback(code: str, state: str) -> RedirectResponse:
+    """Google redirects here after Gmail consent.
+
+    Immediately bounces to the Electron deep link so the desktop app
+    receives the authorization code.
+    """
+    params = urllib.parse.urlencode({"code": code, "state": state})
+    deep_link = f"adiuvai://scout/oauth/gmail/callback?{params}"
+    return RedirectResponse(url=deep_link, status_code=302)
+
+
+@router.post("/oauth/gmail/callback")
+async def scout_gmail_oauth_callback(
+    body: _ScoutGmailCallbackBody,
+    db: AsyncSession = Depends(get_session),
+    current_user: UserProfile = Depends(get_current_user),
+) -> dict:
+    """Exchange the Gmail authorization code and store the encrypted token on the scout.
+
+    Called by the Electron app after it receives the deep-link callback with
+    the ``code`` and ``state`` params.
+    """
+    entry = _pending_scout_oauth_states.pop(body.state, None)
+    if (
+        entry is None
+        or entry["expires_at"] < time.time()
+        or entry["user_id"] != current_user.id
+    ):
+        raise HTTPException(status.HTTP_401_UNAUTHORIZED, "Invalid or expired OAuth state")
+
+    code_verifier = entry["code_verifier"]
+    mode = entry["mode"]
+    scout_id = entry.get("scout_id")
+
+    redirect_uri = _scout_gmail_redirect_uri()
+
+    import httpx
+    async with httpx.AsyncClient() as client:
+        response = await client.post(
+            _GOOGLE_TOKEN_URL,
+            data={
+                "client_id": settings.GOOGLE_AUTH_CLIENT_ID,
+                "client_secret": settings.GOOGLE_AUTH_CLIENT_SECRET,
+                "code": body.code,
+                "code_verifier": code_verifier,
+                "grant_type": "authorization_code",
+                "redirect_uri": redirect_uri,
+            },
+        )
+    try:
+        response.raise_for_status()
+    except httpx.HTTPStatusError as exc:
+        logger.error("Gmail token exchange failed: %s", exc.response.text)
+        raise HTTPException(status.HTTP_502_BAD_GATEWAY, "Failed to exchange Gmail authorization code")
+
+    token_data = response.json()
+
+    creds_dict: dict = {
+        "token": token_data["access_token"],
+        "refresh_token": token_data.get("refresh_token"),
+        "token_uri": _GOOGLE_TOKEN_URL,
+        "client_id": settings.GOOGLE_AUTH_CLIENT_ID,
+        "client_secret": settings.GOOGLE_AUTH_CLIENT_SECRET,
+        "scopes": [
+            "https://www.googleapis.com/auth/gmail.readonly",
+            "https://www.googleapis.com/auth/gmail.modify",
+        ],
+    }
+    encrypted = encrypt_token(creds_dict)
+
+    # Fetch the connected Gmail address for display.
+    gmail_address: str | None = None
+    try:
+        from googleapiclient.discovery import build
+        from google.oauth2.credentials import Credentials
+
+        def _fetch_email() -> str | None:
+            creds = Credentials(
+                token=creds_dict["token"],
+                refresh_token=creds_dict.get("refresh_token"),
+                token_uri=creds_dict["token_uri"],
+                client_id=creds_dict["client_id"],
+                client_secret=creds_dict["client_secret"],
+                scopes=creds_dict["scopes"],
+            )
+            service = build("gmail", "v1", credentials=creds, cache_discovery=False)
+            profile = service.users().getProfile(userId="me").execute()
+            return profile.get("emailAddress")
+
+        gmail_address = await asyncio.to_thread(_fetch_email)
+    except Exception:
+        logger.exception("failed to fetch gmail address (mode=%s)", mode)
+
+    if mode == "create":
+        # Do NOT create a scout yet. Hold the encrypted token + address in the
+        # transient in-memory session; the scout is created at finalize.
+        entry["token_encrypted"] = encrypted
+        entry["gmail_address"] = gmail_address
+        entry["expires_at"] = time.time() + _SCOUT_OAUTH_TTL_SECONDS
+        _pending_scout_oauth_states[body.state] = entry
+        return {"ok": True, "session_id": body.state, "gmail_address": gmail_address}
+
+    # mode == "reconnect": update the existing scout in place.
+    scout = await db.get(CloudScoutConfig, scout_id)
+    if scout is None or scout.user_id != current_user.id:
+        raise HTTPException(status.HTTP_404_NOT_FOUND, "Scout not found")
+    scout.oauth_token_encrypted = encrypted
+    scout.gmail_address = gmail_address
+
+    await db.commit()
+
+    # Attempt to set up Gmail push watch so we start receiving Pub/Sub notifications.
+    try:
+        connector = get_connector("gmail")
+        await connector.setup_watch(scout)
+        await db.commit()
+    except KeyError:
+        logger.warning("gmail connector not registered — skipping setup_watch for scout %s", scout_id)
+    except Exception:
+        logger.exception("setup_watch failed for scout %s", scout_id)
+
+    return {"ok": True, "session_id": None, "gmail_address": gmail_address}
+
+
+@router.get("/oauth/gmail/session-labels")
+async def scout_gmail_session_labels(
+    session: str,
+    current_user: UserProfile = Depends(get_current_user),
+) -> list[dict]:
+    """List Gmail labels for a pending create-mode OAuth session (no scout row yet).
+
+    Builds a Gmail service from the session's transient decrypted token.
+    Returns [] on any error.
+    """
+    entry = _pending_scout_oauth_states.get(session)
+    if (
+        entry is None
+        or entry["expires_at"] < time.time()
+        or entry["user_id"] != current_user.id
+        or entry.get("token_encrypted") is None
+    ):
+        raise HTTPException(status.HTTP_404_NOT_FOUND, "Session not found or expired")
+
+    try:
+        from app.scouts.connectors.gmail import _gmail_service_from_token
+
+        creds = decrypt_token(entry["token_encrypted"])
+
+        def _sync() -> list[dict]:
+            service = _gmail_service_from_token(creds)
+            resp = service.users().labels().list(userId="me").execute()
+            return [{"id": lbl["id"], "name": lbl["name"]} for lbl in resp.get("labels", [])]
+
+        return await asyncio.to_thread(_sync)
+    except Exception:
+        logger.exception("session-labels failed for session %s", session)
+        return []
+
+
+@router.post("/cloud/finalize", response_model=CloudScoutResponse, status_code=status.HTTP_201_CREATED)
+async def finalize_cloud_scout(
+    body: _ScoutGmailFinalizeBody,
+    db: AsyncSession = Depends(get_session),
+    current_user: UserProfile = Depends(get_current_user),
+):
+    """Create the cloud scout from a completed create-mode OAuth session.
+
+    This is the only path that persists the Gmail token for a newly-created
+    scout. Abandoned flows never reach here, so they leave no orphan rows.
+    """
+    entry = _pending_scout_oauth_states.pop(body.session, None)
+    if (
+        entry is None
+        or entry["expires_at"] < time.time()
+        or entry["user_id"] != current_user.id
+        or entry.get("mode") != "create"
+        or entry.get("token_encrypted") is None
+    ):
+        raise HTTPException(status.HTTP_401_UNAUTHORIZED, "Invalid or expired OAuth session")
+
+    draft = entry["draft"] or {}
+    scout = CloudScoutConfig(
+        id=str(uuid.uuid4()),
+        user_id=current_user.id,
+        provider="gmail",
+        name=draft.get("name", ""),
+        data_types=[],
+        prompt_template=draft.get("prompt_template", ""),
+        filter_config=body.filter_config,
+        schedule_cron=_DEFAULT_CLOUD_SCHEDULE,
+        auto_trash_spam=draft.get("auto_trash_spam", False),
+        enabled=True,
+        oauth_token_encrypted=entry["token_encrypted"],
+        gmail_address=entry.get("gmail_address"),
+    )
+    db.add(scout)
+    await db.commit()
+    await db.refresh(scout)
+
+    # Best-effort Gmail push watch — failure must not block scout creation.
+    try:
+        connector = get_connector("gmail")
+        await connector.setup_watch(scout)
+        await db.commit()
+    except KeyError:
+        logger.warning("gmail connector not registered — skipping setup_watch for scout %s", scout.id)
+    except Exception:
+        logger.exception("setup_watch failed for scout %s", scout.id)
+
+    return _to_cloud_response(scout)

api/app/config/settings.py

@@ -58,6 +58,16 @@ class Settings(BaseSettings):
     # Prod: https://api.adiuvai.com/api/v1/auth/oauth/google/web-callback
     OAUTH_REDIRECT_URI: str = "http://localhost:8000/api/v1/auth/oauth/google/web-callback"
 
+    # Gmail Pub/Sub topic for push notifications.
+    # Full resource name, e.g. "projects/my-project/topics/gmail-push".
+    # Leave empty in dev — setup_watch will skip registration gracefully.
+    GMAIL_PUBSUB_TOPIC: str = ""
+    # OIDC token audience for Pub/Sub push subscription JWT verification.
+    # Set to the service account email or audience string configured in the
+    # Pub/Sub push subscription. Leave empty in dev to skip verification
+    # (a warning is logged — never silent in production).
+    GMAIL_PUBSUB_AUDIENCE: str = ""
+
     # Fernet key (URL-safe base64, 32-byte key) for at-rest encryption of OAuth
     # tokens stored in cloud_agent_configs.oauth_token_encrypted.
     # Generate with: from cryptography.fernet import Fernet; Fernet.generate_key()

api/app/main.py

@@ -77,8 +77,98 @@ async def _memory_cron_tick() -> None:
         _log.warning("memory cron tick: failed: %s", exc)
 
 
+async def _scout_cron_tick() -> None:
+    """Every-15-min cron: poll enabled cloud scouts (cron-fallback; push is primary).
+
+    Skips any scout whose ``last_run_at`` is within the last 5 minutes so
+    a push notification and the fallback cron don't double-fire within the
+    same window.
+    """
+    import logging  # noqa: PLC0415
+    import uuid  # noqa: PLC0415
+    from datetime import datetime, timezone  # noqa: PLC0415
+
+    _log = logging.getLogger(__name__)
+    _log.info("scout cron tick: starting")
+    try:
+        from app.db import async_session  # noqa: PLC0415
+        from app.models import CloudScoutConfig  # noqa: PLC0415
+        from app.scouts.engine import ScoutEngine  # noqa: PLC0415
+        from sqlalchemy import select  # noqa: PLC0415
+
+        async with async_session() as session:
+            scouts = (await session.execute(
+                select(CloudScoutConfig).where(CloudScoutConfig.enabled == True)  # noqa: E712
+            )).scalars().all()
+
+        engine = ScoutEngine()
+        triggered = 0
+        for scout in scouts:
+            # Rate-limit guard: push is primary; skip if ran within 5 minutes.
+            if scout.last_run_at:
+                elapsed = (datetime.now(tz=timezone.utc) - scout.last_run_at).total_seconds()
+                if elapsed < 300:
+                    continue
+            try:
+                await engine.trigger_scout(uuid.UUID(str(scout.id)))
+                triggered += 1
+            except Exception as exc:
+                _log.warning("scout cron tick: trigger failed scout=%s: %s", scout.id, exc)
+
+        _log.info("scout cron tick: done triggered=%d total=%d", triggered, len(scouts))
+    except Exception as exc:
+        _log.warning("scout cron tick: failed: %s", exc)
+
+
+async def _scout_watch_renewal_tick() -> None:
+    """Every-24-hour cron: re-issue Gmail users.watch for scouts expiring within 24h.
+
+    Handles missing or misconfigured connectors gracefully — logs and continues.
+    """
+    import logging  # noqa: PLC0415
+    from datetime import datetime, timedelta, timezone  # noqa: PLC0415
+
+    _log = logging.getLogger(__name__)
+    _log.info("scout watch renewal tick: starting")
+    try:
+        from app.db import async_session  # noqa: PLC0415
+        from app.models import CloudScoutConfig  # noqa: PLC0415
+        from app.scouts.connectors.registry import get_connector  # noqa: PLC0415
+        from sqlalchemy import select  # noqa: PLC0415
+
+        threshold = datetime.now(tz=timezone.utc) + timedelta(hours=24)
+        renewed = 0
+        async with async_session() as session:
+            scouts = (await session.execute(
+                select(CloudScoutConfig).where(
+                    CloudScoutConfig.enabled == True,  # noqa: E712
+                    CloudScoutConfig.provider == "gmail",
+                    CloudScoutConfig.gmail_watch_expires_at <= threshold,
+                )
+            )).scalars().all()
+
+            for scout in scouts:
+                try:
+                    connector = get_connector("gmail")
+                    await connector.renew_watch(scout)
+                    renewed += 1
+                except Exception:
+                    _log.exception("scout watch renewal tick: renew failed scout=%s", scout.id)
+
+            await session.commit()
+
+        _log.info("scout watch renewal tick: done renewed=%d", renewed)
+    except Exception as exc:
+        _log.warning("scout watch renewal tick: failed: %s", exc)
+
+
 @asynccontextmanager
 async def lifespan(app: FastAPI):
+    # Startup: register source connectors.
+    from app.scouts.connectors.gmail import GmailConnector  # noqa: PLC0415
+    from app.scouts.connectors.registry import register_connector  # noqa: PLC0415
+    register_connector(GmailConnector())
+
     # Startup: ensure agent tool modules are loaded.
     import app.agents  # noqa: F401
 
@@ -89,6 +179,14 @@ async def lifespan(app: FastAPI):
         scheduler = AsyncIOScheduler()
         scheduler.add_job(_memory_cron_tick, "interval", hours=1, id="memory_cron")
         scheduler.add_job(_memory_audit_cron_tick, "interval", weeks=1, id="memory_audit_cron")
+        scheduler.add_job(
+            _scout_cron_tick, "interval", minutes=15,
+            id="scout_cron_tick", replace_existing=True,
+        )
+        scheduler.add_job(
+            _scout_watch_renewal_tick, "interval", hours=24,
+            id="scout_watch_renewal_tick", replace_existing=True,
+        )
         scheduler.start()
         logging.getLogger(__name__).info("memory cron scheduler started (interval=1h)")
 
@@ -124,14 +222,15 @@ def create_app() -> FastAPI:
     app.add_middleware(SanitizerMiddleware)
     app.add_middleware(TierRateLimitMiddleware)
 
-    from app.api.routes import scouts, auth, billing, chat, device_ws, memory
+    from app.api.routes import scouts, auth, billing, chat, device_ws, memory, scout_webhooks
 
-    app.include_router(auth.router,       prefix="/api/v1")
+    app.include_router(auth.router,           prefix="/api/v1")
-    app.include_router(chat.router,       prefix="/api/v1")
+    app.include_router(chat.router,           prefix="/api/v1")
-    app.include_router(billing.router,    prefix="/api/v1")
+    app.include_router(billing.router,        prefix="/api/v1")
-    app.include_router(scouts.router,     prefix="/api/v1")
+    app.include_router(scouts.router,         prefix="/api/v1")
-    app.include_router(device_ws.router,  prefix="/api/v1")
+    app.include_router(scout_webhooks.router, prefix="/api/v1")
-    app.include_router(memory.router,     prefix="/api/v1")
+    app.include_router(device_ws.router,      prefix="/api/v1")
+    app.include_router(memory.router,         prefix="/api/v1")
 
     @app.get("/api/v1/health", tags=["health"])
     async def health() -> dict:

api/app/models.py

@@ -223,6 +223,7 @@ class CloudScoutConfig(Base):
     gmail_history_id: Mapped[str | None] = mapped_column(String(64), nullable=True)
     gmail_watch_expires_at: Mapped[datetime | None] = mapped_column(DateTime(timezone=True), nullable=True)
     device_inactivity_pause_days: Mapped[int] = mapped_column(Integer, nullable=False, default=14, server_default="14")
+    gmail_address: Mapped[str | None] = mapped_column(String(320), nullable=True)
 
     run_logs: Mapped[list["ScoutRunLog"]] = relationship(
         back_populates="cloud_scout",

api/app/schemas/__init__.py

@@ -276,6 +276,46 @@ class ScoutRunLogResponse(BaseModel):
     completed_at: int | None
 
 
+# ── Cloud Scout CRUD ──────────────────────────────────────────────────
+
+class CloudScoutCreateRequest(BaseModel):
+    name: str
+    provider: Literal["gmail", "teams", "outlook"]
+    data_types: list[str] = Field(default_factory=list)
+    prompt_template: str = ""
+    schedule_cron: str | None = None        # None → server default
+    filter_config: dict | None = None
+    auto_trash_spam: bool = False
+
+
+class CloudScoutUpdateRequest(BaseModel):
+    name: str | None = None
+    data_types: list[str] | None = None
+    prompt_template: str | None = None
+    schedule_cron: str | None = None
+    filter_config: dict | None = None
+    auto_trash_spam: bool | None = None
+    enabled: bool | None = None
+
+
+class CloudScoutResponse(BaseModel):
+    id: str
+    user_id: str
+    provider: str
+    name: str
+    data_types: list[str]
+    prompt_template: str
+    schedule_cron: str
+    filter_config: dict | None
+    auto_trash_spam: bool
+    enabled: bool
+    last_run_at: int | None
+    gmail_address: str | None
+    oauth_connected: bool
+    created_at: int
+    updated_at: int
+
+
 # ── Chatbot Journey ───────────────────────────────────────────────────
 
 

api/app/scouts/connectors/gmail.py

@@ -0,0 +1,248 @@
+"""Gmail SourceConnector — wraps the existing GmailClient.
+
+Responsibilities:
+  * list_new: incremental fetch since the scout's stored gmail_history_id
+  * fetch_metadata: subject + sender + snippet only (Gmail metadata format)
+  * fetch_content: full body text — transient, never persisted by engine
+  * archive: move a message to Gmail Trash (recoverable for 30 days)
+  * setup_watch / renew_watch: Gmail push notifications via Pub/Sub
+"""
+
+from __future__ import annotations
+
+import asyncio
+import logging
+from datetime import datetime, timezone
+
+from app.config.settings import settings
+from app.integrations import decrypt_token
+from app.scouts.connectors.base import ItemContent, ItemMetadata, ItemRef
+
+logger = logging.getLogger(__name__)
+
+
+def _extract_plain_text_body(payload: dict) -> str:
+    """Recursively walk a Gmail message payload to find text/plain content."""
+    import base64
+    mime_type = payload.get("mimeType", "")
+    if mime_type == "text/plain":
+        data = payload.get("body", {}).get("data", "")
+        if data:
+            return base64.urlsafe_b64decode(data + "==").decode("utf-8", errors="replace")
+        return ""
+    if mime_type.startswith("multipart/"):
+        for part in payload.get("parts", []):
+            text = _extract_plain_text_body(part)
+            if text:
+                return text
+    # text/html fallback: strip tags rudimentarily if no text/plain part
+    if mime_type == "text/html":
+        data = payload.get("body", {}).get("data", "")
+        if data:
+            import re
+            html = base64.urlsafe_b64decode(data + "==").decode("utf-8", errors="replace")
+            return re.sub(r"<[^>]+>", " ", html)
+    return ""
+
+
+def _gmail_service_from_token(creds_info: dict):
+    """Build a synchronous Gmail API client from a decrypted credentials dict.
+
+    Shared by ``_get_gmail_service`` (scout-backed) and the pending-session
+    OAuth flow which has a raw token but no scout row yet.
+    """
+    from googleapiclient.discovery import build
+    from google.oauth2.credentials import Credentials
+
+    credentials = Credentials(
+        token=creds_info.get("token"),
+        refresh_token=creds_info.get("refresh_token"),
+        token_uri=creds_info.get("token_uri", "https://oauth2.googleapis.com/token"),
+        client_id=creds_info.get("client_id"),
+        client_secret=creds_info.get("client_secret"),
+        scopes=creds_info.get("scopes"),
+    )
+    return build("gmail", "v1", credentials=credentials, cache_discovery=False)
+
+
+def _get_gmail_service(scout):
+    """Return a synchronous Google API client for low-level metadata/history calls."""
+    creds_info = decrypt_token(scout.oauth_token_encrypted)
+    return _gmail_service_from_token(creds_info)
+
+
+class GmailConnector:
+    source_type = "gmail"
+
+    # ── list_new ──────────────────────────────────────────────────────────
+
+    async def list_new(self, scout) -> list[ItemRef]:
+        """Return new message refs since scout.gmail_history_id.
+
+        On first run (gmail_history_id is None/empty), records the current
+        historyId without backfilling — avoids flooding the user with old mail.
+        Updates scout.gmail_history_id in-place (caller must persist to DB).
+        """
+        def _sync() -> tuple[list[ItemRef], str | None]:
+            service = _get_gmail_service(scout)
+            history_id = scout.gmail_history_id
+            refs: list[ItemRef] = []
+            new_history_id = history_id
+
+            if history_id:
+                resp = (
+                    service.users()
+                    .history()
+                    .list(
+                        userId="me",
+                        startHistoryId=history_id,
+                        historyTypes=["messageAdded"],
+                    )
+                    .execute()
+                )
+                for entry in resp.get("history", []):
+                    for added in entry.get("messagesAdded", []):
+                        refs.append(ItemRef(source_msg_ref=added["message"]["id"]))
+                new_history_id = resp.get("historyId", history_id)
+            else:
+                # First run: capture baseline history id without backfilling.
+                profile = service.users().getProfile(userId="me").execute()
+                new_history_id = profile["historyId"]
+
+            return refs, new_history_id
+
+        refs, new_history_id = await asyncio.to_thread(_sync)
+        if new_history_id and new_history_id != scout.gmail_history_id:
+            scout.gmail_history_id = new_history_id
+        return refs
+
+    # ── fetch_metadata ────────────────────────────────────────────────────
+
+    async def fetch_metadata(self, scout, ref: ItemRef) -> ItemMetadata:
+        """Fetch subject, sender, snippet only — uses Gmail metadata format (no body)."""
+
+        def _sync() -> ItemMetadata:
+            service = _get_gmail_service(scout)
+            msg = (
+                service.users()
+                .messages()
+                .get(
+                    userId="me",
+                    id=ref.source_msg_ref,
+                    format="metadata",
+                    metadataHeaders=["Subject", "From", "Date"],
+                )
+                .execute()
+            )
+            headers = {
+                h["name"]: h["value"]
+                for h in msg.get("payload", {}).get("headers", [])
+            }
+            return ItemMetadata(
+                subject=headers.get("Subject"),
+                sender=headers.get("From"),
+                snippet=msg.get("snippet"),
+                received_at=None,
+            )
+
+        return await asyncio.to_thread(_sync)
+
+    # ── fetch_content ─────────────────────────────────────────────────────
+
+    async def fetch_content(self, scout, ref: ItemRef) -> ItemContent:
+        """Fetch full body text for a single message — transient, must not be persisted."""
+
+        def _sync() -> ItemContent:
+            service = _get_gmail_service(scout)
+            msg = service.users().messages().get(
+                userId="me", id=ref.source_msg_ref, format="full",
+            ).execute()
+            headers = {h["name"]: h["value"] for h in msg.get("payload", {}).get("headers", [])}
+            body_text = _extract_plain_text_body(msg.get("payload", {}))
+            return ItemContent(
+                metadata=ItemMetadata(
+                    subject=headers.get("Subject"),
+                    sender=headers.get("From"),
+                    snippet=msg.get("snippet"),
+                    received_at=None,
+                ),
+                body_text=body_text,
+                raw_headers=headers,
+            )
+
+        return await asyncio.to_thread(_sync)
+
+    # ── archive ───────────────────────────────────────────────────────────
+
+    async def archive(self, scout, ref: ItemRef) -> None:
+        """Move the message to Gmail Trash (recoverable for 30 days)."""
+
+        def _sync() -> None:
+            service = _get_gmail_service(scout)
+            service.users().messages().trash(
+                userId="me", id=ref.source_msg_ref
+            ).execute()
+
+        await asyncio.to_thread(_sync)
+
+    # ── watch management ──────────────────────────────────────────────────
+
+    async def setup_watch(self, scout) -> None:
+        """Register a Gmail Pub/Sub push watch for the INBOX label.
+
+        Requires ``settings.GMAIL_PUBSUB_TOPIC`` to be set to the full topic
+        resource name (e.g. ``projects/my-project/topics/gmail-push``).
+        Logs a warning and returns without error if the topic is not configured.
+        """
+        topic = settings.GMAIL_PUBSUB_TOPIC
+        if not topic:
+            logger.warning(
+                "setup_watch: GMAIL_PUBSUB_TOPIC is not configured — skipping watch setup"
+            )
+            return
+
+        def _sync() -> None:
+            service = _get_gmail_service(scout)
+            request_body = {
+                "labelIds": ["INBOX"],
+                "topicName": topic,
+            }
+            resp = service.users().watch(userId="me", body=request_body).execute()
+            scout.gmail_history_id = resp.get("historyId")
+            expiration_ms = resp.get("expiration")
+            if expiration_ms:
+                scout.gmail_watch_expires_at = datetime.fromtimestamp(
+                    int(expiration_ms) / 1000, tz=timezone.utc
+                )
+
+        await asyncio.to_thread(_sync)
+
+    async def renew_watch(self, scout) -> None:
+        """Renew an existing Gmail Pub/Sub watch (same as setup_watch)."""
+        await self.setup_watch(scout)
+
+    async def list_labels(self, scout) -> list[dict]:
+        """Return the account's Gmail labels as [{id, name}]. Empty if no token."""
+        if not scout.oauth_token_encrypted:
+            return []
+
+        def _sync() -> list[dict]:
+            service = _get_gmail_service(scout)
+            resp = service.users().labels().list(userId="me").execute()
+            return [{"id": lbl["id"], "name": lbl["name"]} for lbl in resp.get("labels", [])]
+
+        return await asyncio.to_thread(_sync)
+
+    async def stop_watch(self, scout) -> None:
+        """Stop Gmail push notifications. Swallows errors (watch may be gone)."""
+        if not scout.oauth_token_encrypted:
+            return
+
+        def _sync() -> None:
+            service = _get_gmail_service(scout)
+            service.users().stop(userId="me").execute()
+
+        try:
+            await asyncio.to_thread(_sync)
+        except Exception:
+            logger.exception("stop_watch failed for scout %s", scout.id)

api/app/scouts/engine.py

@@ -28,6 +28,8 @@ from datetime import datetime, timedelta, timezone
 from sqlalchemy import select
 from sqlalchemy.exc import IntegrityError
 
+from app.core.langfuse_client import extract_usage, get_langfuse, get_prompt_or_fallback
+from app.core.llm import get_llm
 from app.db import async_session
 from app.models import CloudScoutConfig, ScoutTriageQueue
 from app.scouts.connectors.base import ItemContent, ItemRef, TriageVerdict
@@ -142,6 +144,7 @@ class ScoutEngine:
                     ScoutTriageQueue.status == "queued",
                 )
             )).scalars().all()
+            logger.info("deliver_pending: user=%s found %d queued rows", user_id, len(rows))
 
             for row in rows:
                 try:
@@ -171,7 +174,9 @@ class ScoutEngine:
                         "payload": None,
                     },
                 }
+                logger.info("deliver_pending: sending proposal id=%s subject=%r", row.id, meta.subject)
                 await ws.send_json(payload)
+                logger.info("deliver_pending: send_json returned for proposal id=%s", row.id)
                 row.status = "delivered"
                 row.delivered_at = datetime.now(tz=timezone.utc)
 
@@ -188,5 +193,81 @@ class ScoutEngine:
             await session.commit()
 
     async def _triage_llm(self, scout: CloudScoutConfig, content: ItemContent) -> TriageVerdict:
-        """Stub — real implementation in Task 24."""
+        """Call the scout-triage-system Langfuse prompt to classify an item as relevant or spam.
-        raise NotImplementedError("Real triage LLM call lands in Task 24")
+
+        Uses gpt-4o-mini with JSON mode. Wraps the LLM call in a Langfuse generation
+        observation when Langfuse is configured.
+        """
+        import json  # noqa: PLC0415
+
+        from langchain_core.messages import HumanMessage, SystemMessage  # noqa: PLC0415
+
+        _TRIAGE_FALLBACK = (
+            "You are a triage classifier for an executive-assistant scout that watches a "
+            "{source_type} feed.\n"
+            'The scout\'s purpose is: "{scout_purpose}".\n\n'
+            "Given one item, decide whether it is RELEVANT (worth surfacing to the user as a "
+            "potential task / event / note / project) or SPAM (advertising, mass marketing, "
+            "phishing, bulk notifications with no actionable content).\n\n"
+            "Item:\n"
+            "  - Subject: {item_subject}\n"
+            "  - From:    {item_sender}\n"
+            "  - Body (truncated): {item_body_truncated_2k}\n\n"
+            'Return JSON only, matching this schema:\n'
+            '  {{"verdict": "relevant" | "spam", "reason": <short string>, "confidence": <0..1>}}\n\n'
+            "Be conservative on \"spam\" — if a message could plausibly be a personal/work "
+            "email, mark it relevant."
+        )
+
+        template, prompt_obj = get_prompt_or_fallback("scout-triage-system", _TRIAGE_FALLBACK)
+
+        body_trunc = (content.body_text or "")[:2000]
+        variables = dict(
+            source_type=scout.provider,
+            scout_purpose=scout.prompt_template or "",
+            item_subject=content.metadata.subject or "",
+            item_sender=content.metadata.sender or "",
+            item_body_truncated_2k=body_trunc,
+        )
+
+        if prompt_obj is not None:
+            try:
+                system_text = prompt_obj.compile(**variables)
+                if isinstance(system_text, list):
+                    system_text = "\n".join(
+                        m.get("content", "") for m in system_text if isinstance(m, dict)
+                    )
+            except Exception as exc:
+                logger.warning("scout triage: compile failed: %s", exc)
+                system_text = template.replace("{{source_type}}", variables["source_type"]) \
+                    .replace("{{scout_purpose}}", variables["scout_purpose"]) \
+                    .replace("{{item_subject}}", variables["item_subject"]) \
+                    .replace("{{item_sender}}", variables["item_sender"]) \
+                    .replace("{{item_body_truncated_2k}}", variables["item_body_truncated_2k"])
+        else:
+            system_text = template.format(**variables)
+
+        llm = get_llm(model="gpt-4o-mini", temperature=0)
+        llm_json = llm.bind(response_format={"type": "json_object"})  # type: ignore[attr-defined]
+
+        messages = [
+            SystemMessage(content=system_text),
+            HumanMessage(content="Classify this item."),
+        ]
+
+        lf = get_langfuse()
+        if lf:
+            with lf.start_as_current_observation(
+                as_type="generation",
+                name="scout-triage",
+                model="gpt-4o-mini",
+                prompt=prompt_obj,
+                input=messages,
+            ) as gen:
+                response = await llm_json.ainvoke(messages)
+                gen.update(output=response.content, usage=extract_usage(response))
+        else:
+            response = await llm_json.ainvoke(messages)
+
+        data = json.loads(response.content)
+        return TriageVerdict(**data)

api/scripts/inspect_gmail_scout_token.py

@@ -0,0 +1,56 @@
+"""Decrypt and inspect the Gmail scout's stored OAuth token.
+
+Shows what scopes were granted at consent time. If gmail.readonly / gmail.modify
+are missing, the consent screen didn't actually grant them.
+
+Usage:
+    python scripts/inspect_gmail_scout_token.py
+"""
+
+from __future__ import annotations
+
+import asyncio
+import sys
+from pathlib import Path
+
+_API_ROOT = Path(__file__).resolve().parent.parent
+if str(_API_ROOT) not in sys.path:
+    sys.path.insert(0, str(_API_ROOT))
+
+from sqlalchemy import select
+
+from app.db import async_session
+from app.integrations import decrypt_token
+from app.models import CloudScoutConfig
+
+
+async def main() -> None:
+    async with async_session() as session:
+        scouts = (
+            await session.execute(
+                select(CloudScoutConfig).where(CloudScoutConfig.provider == "gmail")
+            )
+        ).scalars().all()
+
+    if not scouts:
+        print("No Gmail scouts found.")
+        return
+
+    for scout in scouts:
+        print(f"\nScout: {scout.name} (id={scout.id})")
+        if not scout.oauth_token_encrypted:
+            print("  (no token stored)")
+            continue
+        try:
+            creds = decrypt_token(scout.oauth_token_encrypted)
+        except Exception as exc:
+            print(f"  decrypt failed: {exc}")
+            continue
+        print(f"  has refresh_token: {bool(creds.get('refresh_token'))}")
+        print(f"  stored scopes:     {creds.get('scopes')}")
+        print(f"  token_uri:         {creds.get('token_uri')}")
+        print(f"  client_id (last 8): ...{(creds.get('client_id') or '')[-8:]}")
+
+
+if __name__ == "__main__":
+    asyncio.run(main())

api/scripts/reset_triage_queue_to_queued.py

@@ -0,0 +1,35 @@
+"""Re-queue all delivered (but not acked) triage rows so deliver_pending sends them again.
+
+Usage:
+    python scripts/reset_triage_queue_to_queued.py
+"""
+
+from __future__ import annotations
+
+import asyncio
+import sys
+from pathlib import Path
+
+_API_ROOT = Path(__file__).resolve().parent.parent
+if str(_API_ROOT) not in sys.path:
+    sys.path.insert(0, str(_API_ROOT))
+
+from sqlalchemy import update
+
+from app.db import async_session
+from app.models import ScoutTriageQueue
+
+
+async def main() -> None:
+    async with async_session() as session:
+        result = await session.execute(
+            update(ScoutTriageQueue)
+            .where(ScoutTriageQueue.status == "delivered")
+            .values(status="queued", delivered_at=None)
+        )
+        await session.commit()
+        print(f"Reset {result.rowcount} rows from delivered → queued")
+
+
+if __name__ == "__main__":
+    asyncio.run(main())

api/scripts/show_gmail_scout_state.py

@@ -0,0 +1,59 @@
+"""Print Gmail scout state for debugging.
+
+Usage:
+    python scripts/show_gmail_scout_state.py
+"""
+
+from __future__ import annotations
+
+import asyncio
+import sys
+from pathlib import Path
+
+_API_ROOT = Path(__file__).resolve().parent.parent
+if str(_API_ROOT) not in sys.path:
+    sys.path.insert(0, str(_API_ROOT))
+
+from sqlalchemy import select, func
+
+from app.db import async_session
+from app.models import CloudScoutConfig, ScoutTriageQueue, ScoutRunLog
+
+
+async def main() -> None:
+    async with async_session() as session:
+        scouts = (
+            await session.execute(
+                select(CloudScoutConfig).where(CloudScoutConfig.provider == "gmail")
+            )
+        ).scalars().all()
+
+        for scout in scouts:
+            print(f"\nScout: {scout.name} (id={scout.id})")
+            print(f"  enabled:                  {scout.enabled}")
+            print(f"  gmail_history_id:         {scout.gmail_history_id}")
+            print(f"  gmail_watch_expires_at:   {scout.gmail_watch_expires_at}")
+            print(f"  auto_trash_spam:          {scout.auto_trash_spam}")
+            print(f"  last_run_at:              {scout.last_run_at}")
+
+            queued_count = (
+                await session.execute(
+                    select(func.count())
+                    .select_from(ScoutTriageQueue)
+                    .where(ScoutTriageQueue.scout_id == scout.id)
+                )
+            ).scalar()
+            print(f"  triage_queue rows:        {queued_count}")
+
+            run_count = (
+                await session.execute(
+                    select(func.count())
+                    .select_from(ScoutRunLog)
+                    .where(ScoutRunLog.scout_id == scout.id)
+                )
+            ).scalar()
+            print(f"  scout_run_logs:           {run_count}")
+
+
+if __name__ == "__main__":
+    asyncio.run(main())

api/scripts/trigger_gmail_scout.py

@@ -0,0 +1,74 @@
+"""Manually trigger the user's Gmail scout for testing.
+
+Usage:
+    python scripts/trigger_gmail_scout.py [user_email]
+
+If user_email omitted, picks the first user with a Gmail scout.
+Runs ScoutEngine.trigger_scout — which calls Gmail history.list since last
+gmail_history_id, fetches each new message, runs LLM triage, inserts queue rows
+for relevant items.
+
+After running, check the queue:
+    psql -d adiuvai -c "select source_msg_ref, triage_verdict, status from scout_triage_queue order by triaged_at desc limit 10"
+
+Then restart the Electron app to trigger deliver_pending → frames → local
+scout_suggestions rows.
+"""
+
+from __future__ import annotations
+
+import asyncio
+import sys
+import uuid
+from pathlib import Path
+
+# Ensure api/ root is importable when running from scripts/ subdir
+_API_ROOT = Path(__file__).resolve().parent.parent
+if str(_API_ROOT) not in sys.path:
+    sys.path.insert(0, str(_API_ROOT))
+
+from sqlalchemy import select
+
+from app.db import async_session
+from app.models import CloudScoutConfig, User
+from app.scouts.connectors.gmail import GmailConnector
+from app.scouts.connectors.registry import register_connector
+from app.scouts.engine import ScoutEngine
+
+
+async def main() -> None:
+    register_connector(GmailConnector())
+
+    target_email = sys.argv[1] if len(sys.argv) > 1 else None
+
+    async with async_session() as session:
+        q = select(CloudScoutConfig).where(
+            CloudScoutConfig.provider == "gmail",
+            CloudScoutConfig.enabled.is_(True),
+        )
+        if target_email:
+            user = (
+                await session.execute(select(User).where(User.email == target_email))
+            ).scalar_one_or_none()
+            if user is None:
+                print(f"No user with email {target_email}")
+                return
+            q = q.where(CloudScoutConfig.user_id == user.id)
+
+        scouts = (await session.execute(q)).scalars().all()
+
+    if not scouts:
+        print("No enabled Gmail scouts found. Create one in Settings → Scouts first.")
+        return
+
+    for scout in scouts:
+        print(f"Triggering scout id={scout.id} name={scout.name!r} user={scout.user_id}")
+        try:
+            await ScoutEngine().trigger_scout(uuid.UUID(scout.id))
+            print("  → done")
+        except Exception as exc:
+            print(f"  → failed: {exc}")
+
+
+if __name__ == "__main__":
+    asyncio.run(main())