Blame for plugins/platforms/google_chat/adapter.py

"""Google Chat platform adapter.

Inbound: authenticated HTTP callbacks or a Cloud Pub/Sub pull subscription. Outbound:
Chat REST API (synchronous googleapiclient via ``asyncio.to_thread``). The Pub/Sub
callback runs on a background thread, so ``handle_message`` is scheduled thread-safely
onto the loop and never awaited there. Only MESSAGE events reach the agent; membership
events cache the bot id, card clicks are ACK'd only.
"""

from __future__ import annotations

import asyncio
import contextlib
import importlib
import json
import logging
import os
import random
import re
import threading
import time
from pathlib import Path as _Path
from typing import Any, Callable, Dict, List, Optional, Tuple
from urllib.parse import urlparse

from agent.secret_scope import is_multiplex_active
from gateway.platforms._shared import (
    get_scoped_secret as _get_scoped_secret, seed_extra_from_env as _seed_extra_from_env, send_error
)

from .cards import card_spec_to_cards_v2, format_message as _format_message


def _adc_would_borrow_foreign_credentials() -> bool:
    """True when ADC would read another profile's SA from the process env under
    multiplexing (``google.auth.default()`` consults ``os.environ`` directly)."""
    return is_multiplex_active() and bool(
        os.environ.get("GOOGLE_CHAT_SERVICE_ACCOUNT_JSON") or os.environ.get("GOOGLE_APPLICATION_CREDENTIALS")
    )

# Heavy google imports are deferred to first adapter use (~110ms / ~33MB on every CLI
# start). ``_load_google_modules()`` rebinds these; ``HttpError = Exception`` keeps
# ``except HttpError`` valid meanwhile.
GOOGLE_CHAT_AVAILABLE: bool = False
httplib2 = pubsub_v1 = gax_exceptions = service_account = AuthorizedHttp = build_service = MediaFileUpload = None  # type: ignore
HttpError: Any = Exception  # type: ignore

_google_modules_loaded: bool = False
# (global name, module, attribute-or-None) rebound by ``_load_google_modules``.
_GOOGLE_IMPORTS = (
    ("httplib2", "httplib2", None), ("pubsub_v1", "google.cloud.pubsub_v1", None),
    ("gax_exceptions", "google.api_core.exceptions", None), ("service_account", "google.oauth2.service_account", None),
    ("AuthorizedHttp", "google_auth_httplib2", "AuthorizedHttp"), ("build_service", "googleapiclient.discovery", "build"),
    ("HttpError", "googleapiclient.errors", "HttpError"), ("MediaFileUpload", "googleapiclient.http", "MediaFileUpload"),
)
_GOOGLE_ID_TOKEN_CERTS_TTL_SECONDS = 300
_google_id_token_request: Any = None
_google_id_token_request_lock = threading.Lock()


class _CachedGoogleAuthRequest:
    """Caches successful GET responses (Google cert fetches) for ``ttl_seconds``."""

    def __init__(self, request: Any, ttl_seconds: int = _GOOGLE_ID_TOKEN_CERTS_TTL_SECONDS) -> None:
        self._request, self._ttl_seconds, self._lock = request, ttl_seconds, threading.Lock()
        self._cache: Dict[Tuple[str, str], Tuple[float, Any]] = {}

    def __call__(self, url: str, method: str = "GET", **kwargs: Any) -> Any:
        cache_key = (method.upper(), url)
        if cache_key[0] != "GET":
            return self._request(url=url, method=method, **kwargs)
        now = time.monotonic()
        with self._lock:
            cached = self._cache.get(cache_key)
            if cached and cached[0] > now:
                return cached[1]
        response = self._request(url=url, method=method, **kwargs)
        if getattr(response, "status", None) == 200:
            with self._lock:
                self._cache[cache_key] = (now + self._ttl_seconds, response)
        return response


def _get_google_id_token_request() -> Any:
    global _google_id_token_request
    with _google_id_token_request_lock:
        if _google_id_token_request is None:
            try:
                from google.auth.transport import requests as google_requests
            except ImportError as exc:
                raise RuntimeError("google-auth is required for Google Chat HTTP callbacks") from exc
            _google_id_token_request = _CachedGoogleAuthRequest(google_requests.Request())
        return _google_id_token_request


def _verify_google_id_token(token: str, audience: str) -> Dict[str, Any]:
    try:
        from google.oauth2 import id_token
    except ImportError as exc:
        raise RuntimeError("google-auth is required for Google Chat HTTP callbacks") from exc
    return id_token.verify_oauth2_token(token, _get_google_id_token_request(), audience)


def _load_google_modules() -> bool:
    """Lazily import the google stack (idempotent); True when the optional deps exist."""
    global GOOGLE_CHAT_AVAILABLE, _google_modules_loaded
    if _google_modules_loaded:
        return GOOGLE_CHAT_AVAILABLE
    _google_modules_loaded = True
    try:
        loaded = {
            name: getattr(importlib.import_module(module), attr) if attr else importlib.import_module(module)
            for name, module, attr in _GOOGLE_IMPORTS
        }
    except ImportError:
        GOOGLE_CHAT_AVAILABLE = False
        return False
    globals().update(loaded)
    GOOGLE_CHAT_AVAILABLE = True
    return True

from gateway.config import Platform, PlatformConfig

# Register the dynamic enum member at import time so ``Platform.GOOGLE_CHAT``
# resolves before any adapter instance exists.
Platform("google_chat")
from gateway.platforms.helpers import MessageDeduplicator
from gateway.platforms.base import (
    gateway_trust_env, BasePlatformAdapter, SendResult,
    cache_audio_from_bytes_async, cache_document_from_bytes_async, cache_image_from_bytes_async,
    cache_video_from_bytes_async,
)
from gateway.platforms.event import MessageEvent, MessageType, ProcessingOutcome

# Pinned to the legacy module path so operator log filters keep matching.
logger = logging.getLogger("gateway.platforms.google_chat")

_SUBSCRIPTION_PATH_RE = re.compile(r"^projects/(?P<project>[^/]+)/subscriptions/(?P<sub>[^/]+)$")
# chat.bot covers the bot's own messaging ops; it CANNOT call media.upload
# (user OAuth required — see ``oauth.py``).
_CHAT_SCOPES = ["https://www.googleapis.com/auth/chat.bot", "https://www.googleapis.com/auth/pubsub"]
_MAX_TEXT_LENGTH = 4000  # Chat limit is 4096; leave margin.
_RATE_LIMIT_WARN_THRESHOLD = 5
# Bounded outbound retry for transient 429/5xx so a true outage surfaces quickly.
_RETRY_MAX_ATTEMPTS, _RETRY_BASE_DELAY, _RETRY_MAX_DELAY, _RETRY_JITTER = 3, 1.0, 8.0, 0.3
_RETRYABLE_HTTP_STATUSES = frozenset({429, 500, 502, 503, 504})
_TRANSPORT_ERROR_PHRASES = ("timeout", "timed out", "broken pipe", "remote disconnected")
# Left in ``_typing_messages`` after ``send()`` patched the typing card: stops
# ``_keep_typing`` from creating a fresh card and ``stop_typing`` from deleting
# (tombstoning) the response we just patched.
_TYPING_CONSUMED_SENTINEL = "<consumed>"
# SSRF guard: attachment download URIs must target a Google-owned https host
# (else the SA bearer token could be sent to e.g. the GCE metadata service).
_TRUSTED_ATTACHMENT_HOSTS = (
    "googleapis.com", "chat.google.com", "drive.google.com", "docs.google.com",
    "lh3.googleusercontent.com", "lh4.googleusercontent.com", "lh5.googleusercontent.com", "lh6.googleusercontent.com",
)
_REDACTIONS = (
    (re.compile(r"projects/[^/\s]+/subscriptions/[^/\s]+"), "projects/<redacted>/subscriptions/<redacted>"),
    (re.compile(r"projects/[^/\s]+/topics/[^/\s]+"), "projects/<redacted>/topics/<redacted>"),
    (re.compile(r"[a-zA-Z0-9_.+-]+@[a-zA-Z0-9-]+\.iam\.gserviceaccount\.com"), "<sa>@<project>.iam.gserviceaccount.com"),
)
_MIME_MESSAGE_TYPES = (("image/", MessageType.PHOTO), ("audio/", MessageType.AUDIO), ("video/", MessageType.VIDEO))
_MEDIA_CACHERS = (
    ("image/", cache_image_from_bytes_async, ".jpg"), ("audio/", cache_audio_from_bytes_async, ".ogg"),
    ("video/", cache_video_from_bytes_async, ".mp4"),
)


def _http_status(exc: BaseException) -> Any:
    """``resp.status`` of a googleapiclient HttpError, or None."""
    return getattr(getattr(exc, "resp", None), "status", None)


def _is_retryable_error(exc: BaseException) -> bool:
    """True for transient failures (429, 5xx, transport errors); auth/4xx are permanent."""
    status = _http_status(exc)
    if isinstance(status, int):
        return status in _RETRYABLE_HTTP_STATUSES
    # SSL/socket errors carry no HTTP status: match common transport wording.
    text = str(exc).lower()
    return any(p in text for p in _TRANSPORT_ERROR_PHRASES) or (
        "connection" in text and any(w in text for w in ("reset", "refused", "aborted"))
    )


def check_google_chat_requirements() -> bool:
    """PASSIVE deps probe; must never install. Registry ``check_fn`` uses this via ``_check_for_registry``."""
    return _load_google_modules()


def ensure_google_chat_deps() -> bool:
    """ACTIVE installer (registry ``ensure_deps_fn``).

    Routes through ``tools.lazy_deps`` so sealed hosted/Docker images write
    ``HERMES_LAZY_INSTALL_TARGET`` instead of the read-only venv. Resets the
    failed-import cache so ``create_adapter()`` can load modules after install.
    ``FeatureUnavailable`` propagates: the registry logs its ``reason`` (quarantine
    404, no writable target, network), which is exactly what a hosted operator needs.
    """
    global _google_modules_loaded, GOOGLE_CHAT_AVAILABLE
    if GOOGLE_CHAT_AVAILABLE:
        return True
    from tools.lazy_deps import ensure as _lazy_ensure
    _lazy_ensure("platform.google_chat", prompt=False)
    _google_modules_loaded = False
    return _load_google_modules()


def _is_google_owned_host(url: str) -> bool:
    """Return True iff *url* is https and targets a Google-owned domain."""
    try:
        parsed = urlparse(url)
    except Exception:
        return False
    host = (parsed.hostname or "").lower()
    if parsed.scheme != "https" or not host:
        return False
    return any(host == h or host.endswith("." + h) for h in _TRUSTED_ATTACHMENT_HOSTS)


def _redact_sensitive(text: str) -> str:
    """Redact Pub/Sub resource paths and SA emails from user-facing error strings."""
    if not text:
        return text
    for pattern, repl in _REDACTIONS:
        text = pattern.sub(repl, text)
    return text


def _mime_for_message_type(mime: str) -> MessageType:
    """Map a MIME string to a MessageType; non-media falls through to DOCUMENT."""
    for prefix, message_type in _MIME_MESSAGE_TYPES:
        if mime and mime.startswith(prefix):
            return message_type
    return MessageType.DOCUMENT


class _SACredentialError(Exception):
    """Internal: classified SA-credential load failure (``kind`` + optional cause)."""

    def __init__(self, kind: str, detail: Optional[BaseException] = None) -> None:
        super().__init__(kind)
        self.kind, self.detail = kind, detail


def _load_sa_credentials_from(sa_value: Optional[str]) -> Any:
    """Build SA credentials from a path / inline JSON, or fall back to ADC.
    Raises ``_SACredentialError`` with kind in {inline_invalid, not_found,
    file_invalid, adc_foreign, adc_no_auth, adc_failed}."""
    if sa_value:
        if sa_value.lstrip().startswith("{"):
            try:
                info = json.loads(sa_value)
            except json.JSONDecodeError as exc:
                raise _SACredentialError("inline_invalid", exc) from exc
        elif not os.path.exists(sa_value):
            raise _SACredentialError("not_found")
        else:
            try:
                with open(sa_value, "r", encoding="utf-8") as fh:
                    info = json.load(fh)
            except json.JSONDecodeError as exc:
                raise _SACredentialError("file_invalid", exc) from exc
        return service_account.Credentials.from_service_account_info(info, scopes=_CHAT_SCOPES)
    # No explicit SA — ADC (Cloud Run / GCE workload identity, or gcloud ADC login).
    if _adc_would_borrow_foreign_credentials():
        raise _SACredentialError("adc_foreign")
    try:
        import google.auth as google_auth
    except ImportError:
        raise _SACredentialError("adc_no_auth")
    try:
        credentials, _project = google_auth.default(scopes=_CHAT_SCOPES)
    except Exception as exc:
        raise _SACredentialError("adc_failed", exc) from exc
    return credentials


class _ThreadCountStore:
    """Persisted per-(chat_id, thread_name) inbound counter driving the DM main-flow vs
    side-thread heuristic (0: Chat auto-created the thread for a top-level message; >=1:
    user engaged an existing thread). Persisted because a restart that wiped counts would
    demote active side-threads to main flow and leak context. Format
    ``{"<chat_id>": {"<thread_name>": <int>}}``; missing/corrupt resets to empty."""

    def __init__(self, path: _Path):
        self._path = path
        self._counts: Dict[str, Dict[str, int]] = {}

    def load(self) -> None:
        """Load counts from disk; missing file → empty, corrupt JSON → empty + warn."""
        self._counts = {}
        if not self._path.exists():
            return
        try:
            raw = self._path.read_text(encoding="utf-8")
            data = json.loads(raw) if raw.strip() else {}
        except (json.JSONDecodeError, OSError) as exc:
            fmt = ("[GoogleChat] thread-count store at %s is corrupt; starting fresh: %s" if isinstance(exc, ValueError)
                   else "[GoogleChat] could not read thread-count store at %s: %s")
            logger.warning(fmt, self._path, exc)
            return
        # Anything off-schema is dropped silently.
        for chat_id, threads in (data.items() if isinstance(data, dict) else ()):
            if isinstance(chat_id, str) and isinstance(threads, dict):
                clean = {t: c for t, c in threads.items() if isinstance(t, str) and isinstance(c, int)}
                if clean:
                    self._counts[chat_id] = clean

    def get(self, chat_id: str, thread_name: str) -> int:
        return self._counts.get(chat_id, {}).get(thread_name, 0)

    def incr(self, chat_id: str, thread_name: str) -> int:
        """Increment and write through; returns the PRE-increment value."""
        chat_counts = self._counts.setdefault(chat_id, {})
        prev = chat_counts.get(thread_name, 0)
        chat_counts[thread_name] = prev + 1
        self._save()
        return prev

    def _save(self) -> None:
        """Atomic write; failure is non-fatal (in-memory counts stay consistent)."""
        try:
            self._path.parent.mkdir(parents=True, exist_ok=True)
            tmp = self._path.with_suffix(self._path.suffix + ".tmp")
            tmp.write_text(json.dumps(self._counts, separators=(",", ":")), encoding="utf-8")
            os.replace(tmp, self._path)
        except OSError as exc:
            logger.warning("[GoogleChat] could not persist thread-count store to %s: %s", self._path, exc)


_SA_ERROR_MESSAGES = {
    "inline_invalid": "Inline SA JSON is not valid JSON: {exc}",
    "not_found": "Service Account JSON file not found at configured path.",
    "file_invalid": "Service Account JSON file is not valid JSON: {exc}",
    "adc_foreign": ("Google Chat ADC skipped for this profile: service-account credentials are set in the process "
                    "environment but not in this profile's secret scope. Set GOOGLE_CHAT_SERVICE_ACCOUNT_JSON in this "
                    "profile's .env."),
    "adc_no_auth": ("No Service Account credentials configured. Set GOOGLE_CHAT_SERVICE_ACCOUNT_JSON or "
                    "GOOGLE_APPLICATION_CREDENTIALS, or install google-auth to use Application Default Credentials."),
    "adc_failed": ("No Service Account credentials configured and Application Default Credentials are unavailable. Set "
                   "GOOGLE_CHAT_SERVICE_ACCOUNT_JSON or run ``gcloud auth application-default login``. ADC error: {exc}"),
}


def _thread_body(text: str, thread_id: Optional[str]) -> Dict[str, Any]:
    """``{"text": ...}`` plus ``thread.name`` when replying into a thread."""
    body: Dict[str, Any] = {"text": text}
    if thread_id:
        body["thread"] = {"name": thread_id}
    return body


def _create_kwargs(chat_id: str, body: Dict[str, Any]) -> Dict[str, Any]:
    """messages.create kwargs. With ``thread.name`` we MUST pass
    ``messageReplyOption=REPLY_MESSAGE_FALLBACK_TO_NEW_THREAD`` — the default silently
    ignores thread.name; FALLBACK (vs OR_FAIL) still delivers when the thread is gone."""
    kwargs: Dict[str, Any] = {"parent": chat_id, "body": body}
    if (body.get("thread") or {}).get("name"):
        kwargs["messageReplyOption"] = "REPLY_MESSAGE_FALLBACK_TO_NEW_THREAD"
    return kwargs


class GoogleChatAdapter(BasePlatformAdapter):
    """Google Chat bot adapter: Pub/Sub pull (or HTTP callbacks) + Chat REST API. Env vars
    are documented in gateway/config.py (GOOGLE_CHAT_PROJECT_ID, GOOGLE_CHAT_SUBSCRIPTION_NAME,
    GOOGLE_CHAT_SERVICE_ACCOUNT_JSON + optional allowlist/home-channel/flow-control keys)."""

    MAX_MESSAGE_LENGTH = _MAX_TEXT_LENGTH
    # Pub/Sub supervisor configuration.
    _MAX_RECONNECT_ATTEMPTS = 10
    _RECONNECT_BASE_DELAY = 2.0
    _RECONNECT_MAX_DELAY = 120.0
    _LEGACY_USER_IDENTITY = "__legacy__"

    def __init__(self, config: PlatformConfig):
        # Bundled platform plugins are looked up by enum value (matches Teams, IRC).
        super().__init__(config, Platform("google_chat"))
        # Load here (not only in connect()) so direct method calls see real
        # ``MediaFileUpload`` / ``HttpError`` classes. Idempotent.
        _load_google_modules()
        self._subscriber = self._chat_api = self._credentials = self._streaming_pull_future = None
        self._project_id = self._subscription_path = self._bot_user_id = None  # bot id is users/{id}
        self._supervisor_task: Optional[asyncio.Task] = None
        self._loop: Optional[asyncio.AbstractEventLoop] = None
        # User-authed Chat clients for native ``media.upload`` (bot identity is rejected
        # there) keyed by sender email; ``_user_credentials``/``_user_chat_api`` = LEGACY fallback.
        self._user_chat_api = self._user_credentials = None
        self._user_creds_by_email: Dict[str, Any] = {}
        self._user_chat_api_by_email: Dict[str, Any] = {}
        # chat_id → most-recent inbound sender email (drives per-user token lookup).
        self._last_sender_by_chat: Dict[str, str] = {}
        self._dedup = MessageDeduplicator()
        self._shutting_down = False
        self._typing_messages: Dict[str, str] = {}
        self._clarify_state, self._rate_limit_hits = {}, {}
        # Last inbound thread per space: DMs get a NEW thread per top-level message but users
        # see one conversation, so thread_id leaves the source (stable session key) and is cached here.
        self._last_inbound_thread: Dict[str, str] = {}
        from hermes_constants import get_hermes_home as _get_hermes_home
        self._thread_count_store = _ThreadCountStore(_get_hermes_home() / "google_chat_thread_counts.json")
        # In-flight typing-card creates per chat_id: reserved BEFORE the API call so
        # concurrent _keep_typing calls wait instead of duplicating cards.
        self._typing_card_inflight: Dict[str, asyncio.Event] = {}
        # Typing cards that lost a race with send(); patched away at end of turn.
        self._orphan_typing_messages: Dict[str, List[str]] = {}
        # Snapshot profile-scoped settings now: Pub/Sub callbacks run on threads
        # where the ContextVar secret scope is unavailable.
        extra = self.config.extra
        self._max_messages = self._int_setting(extra, "max_messages", "GOOGLE_CHAT_MAX_MESSAGES", 1)
        self._max_bytes = self._int_setting(extra, "max_bytes", "GOOGLE_CHAT_MAX_BYTES", 16 * 1024 * 1024)
        self._bootstrap_spaces = str(
            extra.get("bootstrap_spaces") or _get_scoped_secret("GOOGLE_CHAT_BOOTSTRAP_SPACES", "") or "").strip()
        self._debug_raw = bool(extra.get("debug_raw") or _get_scoped_secret("GOOGLE_CHAT_DEBUG_RAW"))
        self._http_events_url = self._str_setting(extra, "http_events_url", "GOOGLE_CHAT_HTTP_EVENTS_URL")
        self._http_events_audience = self._str_setting(
            extra, "http_events_audience", "GOOGLE_CHAT_HTTP_EVENTS_AUDIENCE", self._http_events_url)
        self._http_events_service_account_email = self._str_setting(
            extra, "http_events_service_account_email", "GOOGLE_CHAT_HTTP_EVENTS_SERVICE_ACCOUNT_EMAIL").lower()

    @staticmethod
    def _int_setting(extra: Dict[str, Any], key: str, env_name: str, default: int) -> int:
        try:
            return int(extra.get(key) or _get_scoped_secret(env_name, str(default)))
        except (ValueError, TypeError):
            return default

    @staticmethod
    def _str_setting(extra: Dict[str, Any], key: str, env_name: str, fallback: str = "") -> str:
        return (extra.get(key) or _get_scoped_secret(env_name, "") or fallback).strip()

    # -- configuration -------------------------------------------------------
    def _load_sa_credentials(self) -> Any:
        """SA credentials: ``extra['service_account_json']`` → GOOGLE_APPLICATION_CREDENTIALS → ADC.

        Priority: 1. Explicit ``extra['service_account_json']`` (path or inline JSON) 2. 3. Application
        Default Credentials via ``google.auth.default()`` — works on Cloud Run / GCE / GKE with a workload
        identity attached, or locally via ``gcloud auth application-default login``. Lets operators run the
        gateway in GCP without managing SA key files. Pattern lifted from PR #14965.
        """
        sa_path = self.config.extra.get("service_account_json") or _get_scoped_secret("GOOGLE_APPLICATION_CREDENTIALS")
        try:
            credentials = _load_sa_credentials_from(sa_path)
        except _SACredentialError as err:
            message = _SA_ERROR_MESSAGES[err.kind].format(exc=err.detail)
            if err.kind == "not_found":
                raise FileNotFoundError(message)
            raise ValueError(message) from err.detail
        if not sa_path:
            logger.info("[GoogleChat] No SA JSON configured; using Application Default Credentials")
        return credentials

    def _validate_config(self) -> Tuple[str, Optional[str]]:
        """Return (project_id, subscription_path); the latter is None for HTTP inbound.
        Raises ValueError with a sanitized message on any config problem."""
        project_id = (self.config.extra.get("project_id") or "").strip()
        subscription = (self.config.extra.get("subscription_name") or "").strip()
        http_events_url = (self.config.extra.get("http_events_url") or "").strip()
        if subscription:
            match = _SUBSCRIPTION_PATH_RE.match(subscription)
            if not match:
                raise ValueError("GOOGLE_CHAT_SUBSCRIPTION_NAME must match 'projects/<project>/subscriptions/<sub>'.")
            subscription_project = match.group("project")
            if project_id and subscription_project != project_id:
                raise ValueError(
                    "project_id in GOOGLE_CHAT_PROJECT_ID does not match the project embedded in GOOGLE_CHAT_SUBSCRIPTION_NAME."
                )
            return project_id or subscription_project, subscription
        if http_events_url:
            return project_id, None
        if not project_id:
            raise ValueError("GOOGLE_CHAT_PROJECT_ID (or GOOGLE_CLOUD_PROJECT) is not set.")
        raise ValueError(
            "GOOGLE_CHAT_SUBSCRIPTION_NAME (or GOOGLE_CHAT_SUBSCRIPTION) is not set. "
            "Set GOOGLE_CHAT_HTTP_EVENTS_URL for HTTP callback mode."
        )

    # -- loop bridge (Pub/Sub thread -> asyncio loop) ------------------------
    @staticmethod
    def _log_background_failure(future: Any) -> None:
        try:
            future.result()
        except Exception:
            logger.exception("[GoogleChat] Background inbound processing failed")

    @staticmethod
    def _loop_accepts_callbacks(loop: Optional[asyncio.AbstractEventLoop]) -> bool:
        return loop is not None and not bool(getattr(loop, "is_closed", lambda: False)())

    def _submit_on_loop(self, coro: Any) -> None:
        """Schedule a coroutine on the adapter loop from a Pub/Sub callback thread."""
        if not self._loop_accepts_callbacks(loop := self._loop):
            # Shutdown race: safe to drop, Pub/Sub redelivers on next reconnect.
            logger.warning("[GoogleChat] Loop not accepting callbacks; dropping event")
            return
        try:
            from agent.async_utils import safe_schedule_threadsafe
            future = safe_schedule_threadsafe(
                coro, loop, logger=logger, log_message="[GoogleChat] Failed to schedule background callback",
                log_level=logging.WARNING,
            )
        except RuntimeError:
            logger.warning("[GoogleChat] Loop closed between check and submit")
            return
        if future is not None:
            future.add_done_callback(self._log_background_failure)

    # -- bot identity --------------------------------------------------------
    def _bot_id_cache_path(self) -> _Path:
        """Resolved at call time so multiplexed profiles don't share one cache file."""
        from hermes_constants import get_hermes_home as _get_hermes_home
        return _get_hermes_home() / "google_chat_bot_id.json"

    def _load_cached_bot_id(self) -> Optional[str]:
        try:
            return json.loads(self._bot_id_cache_path().read_text(encoding="utf-8")).get("bot_user_id") or None
        except (OSError, json.JSONDecodeError):
            return None

    def _save_cached_bot_id(self, bot_user_id: str) -> None:
        try:
            path = self._bot_id_cache_path()
            path.parent.mkdir(parents=True, exist_ok=True)
            path.write_text(json.dumps({"bot_user_id": bot_user_id}), encoding="utf-8")
        except OSError:
            logger.debug("[GoogleChat] Could not persist bot_user_id cache", exc_info=True)

    async def _resolve_bot_user_id(self) -> Optional[str]:
        """Resolve ``users/{id}`` via members.list on the home channel, then bootstrap
        spaces. None when no space is known (self-filter falls back to ``sender.type == 'BOT'``)."""
        candidate_spaces: List[str] = []
        if self.config.home_channel and self.config.home_channel.chat_id:
            candidate_spaces.append(self.config.home_channel.chat_id)
        if self._bootstrap_spaces:
            candidate_spaces.extend(s.strip() for s in self._bootstrap_spaces.split(",") if s.strip())
        for space in candidate_spaces:
            try:
                members = await asyncio.to_thread(
                    lambda s=space: self._chat_api.spaces().members().list(parent=s, pageSize=50)
                    .execute(http=self._new_authed_http())
                )
            except HttpError as exc:
                logger.debug("[GoogleChat] members.list failed on %s: %s", space, _redact_sensitive(str(exc)))
                continue
            for member in members.get("memberships", []):
                if member.get("member", {}).get("type") == "BOT" and member.get("member", {}).get("name"):
                    return member["member"]["name"]
        return None

    # -- connection lifecycle ------------------------------------------------
    def _connect_failed(self, log_fmt: str, exc: BaseException, code: str, *, retryable: bool) -> bool:
        """Log a redacted connect-time failure, record it as fatal, return False."""
        msg = _redact_sensitive(str(exc))
        logger.error(log_fmt, msg)
        self._set_fatal_error(code=code, message=msg, retryable=retryable)
        return False

    async def _load_user_oauth(self) -> None:
        """Legacy single-user OAuth (per-user tokens load lazily on first send).
        Failure is NON-fatal: only attachments degrade to a text notice."""
        try:
            from .oauth import load_user_credentials as _load_user_creds, build_user_chat_service as _build_user_chat
            from .oauth import list_authorized_emails as _list_emails
            user_creds = await asyncio.to_thread(_load_user_creds)
            if user_creds is not None:
                self._user_credentials = user_creds
                self._user_chat_api = await asyncio.to_thread(lambda: _build_user_chat(user_creds))
                logger.info("[GoogleChat] Legacy user OAuth loaded — fallback attachment delivery enabled")
            authorized = await asyncio.to_thread(_list_emails)
            if authorized:
                logger.info("[GoogleChat] %d per-user OAuth tokens on disk: %s", len(authorized), ", ".join(authorized))
            elif user_creds is None:
                logger.info(
                    "[GoogleChat] No user OAuth tokens at setup — file attachments will degrade to text-only fallback. "
                    "Each user runs /setup-files once in their own DM to enable native attachments."
                )
        except Exception as exc:
            logger.warning(
                "[GoogleChat] User OAuth load failed (attachments will degrade to text-only fallback): %s",
                _redact_sensitive(str(exc)),
            )
            self._user_credentials = self._user_chat_api = None

    async def _check_subscription(self, subscription_path: str, credentials: Any) -> bool:
        """Create the subscriber and verify the subscription exists / SA has access."""
        fatals = {
            gax_exceptions.NotFound: ("subscription_not_found", "Pub/Sub subscription not found at configured path"),
            gax_exceptions.PermissionDenied: (
                "subscription_permission", "Service Account lacks roles/pubsub.subscriber on the subscription"),
        }
        self._subscriber = pubsub_v1.SubscriberClient(credentials=credentials)
        try:
            await asyncio.to_thread(lambda: self._subscriber.get_subscription(request={"subscription": subscription_path}))
        except (gax_exceptions.NotFound, gax_exceptions.PermissionDenied) as exc:
            code, message = fatals[type(exc)]
            self._set_fatal_error(code=code, message=message, retryable=False)
            return False
        except Exception as exc:
            return self._connect_failed("[GoogleChat] subscription.get failed: %s", exc, "subscription_check", retryable=True)
        return True

    async def connect(self, *, is_reconnect: bool = False) -> bool:
        """Validate config, authenticate, start Pub/Sub pull, resolve bot id."""
        # connect() is the gate: everything after sees the real google classes.
        if not _load_google_modules():
            self._set_fatal_error(code="missing_deps", retryable=False,
                                  message="google-cloud-pubsub / google-api-python-client not installed")
            return False
        self._loop = asyncio.get_running_loop()
        try:
            project_id, subscription_path = self._validate_config()
            credentials = self._load_sa_credentials()
        except (ValueError, FileNotFoundError) as exc:
            return self._connect_failed("[GoogleChat] Config validation failed: %s", exc, "config_invalid", retryable=False)
        self._project_id, self._subscription_path, self._credentials = project_id, subscription_path, credentials
        try:
            self._chat_api = await asyncio.to_thread(
                lambda: build_service("chat", "v1", credentials=credentials, cache_discovery=False))
        except Exception as exc:
            return self._connect_failed("[GoogleChat] Failed to build Chat API client: %s", exc, "chat_api_init", retryable=False)
        await self._load_user_oauth()
        try:
            await asyncio.to_thread(self._thread_count_store.load)
        except Exception:
            logger.warning("[GoogleChat] thread-count store load failed (treating all threads as fresh)", exc_info=True)
        if subscription_path is not None and not await self._check_subscription(subscription_path, credentials):
            return False
        # Resolve bot user_id (eager): cache first, then members.list.
        self._bot_user_id = self._load_cached_bot_id()
        if not self._bot_user_id:
            self._bot_user_id = await self._resolve_bot_user_id()
            if self._bot_user_id:
                self._save_cached_bot_id(self._bot_user_id)
            else:
                logger.info("[GoogleChat] bot_user_id not yet resolved; will resolve on first addedToSpace or member lookup")
        self._supervisor_task = asyncio.create_task(self._run_supervisor()) if subscription_path is not None else None
        self._mark_connected()
        logger.info(
            "[GoogleChat] Connected; project=%s, inbound=%s, subscription=%s, "
            "bot_user_id=%s, flow_control(msgs=%s, bytes=%s)",
            project_id or "<unset>", "pubsub" if subscription_path is not None else "http",
            "<redacted>" if subscription_path else "<none>", self._bot_user_id or "<unresolved>",
            self._max_messages, self._max_bytes,
        )
        # Plugin-registered native handlers (ctx.register_platform_handler).
        self._wire_plugin_handlers(None)
        return True

    async def disconnect(self) -> None:
        """Clean shutdown: stop accepting new messages, wait in-flight, close clients."""
        self._shutting_down = True
        if self._supervisor_task and not self._supervisor_task.done():
            self._supervisor_task.cancel()
            with contextlib.suppress(asyncio.CancelledError, asyncio.TimeoutError):
                await asyncio.wait_for(self._supervisor_task, timeout=5.0)
        if (future := self._streaming_pull_future) is not None:
            with contextlib.suppress(Exception):
                future.cancel()
                await asyncio.to_thread(future.result, 10.0)
            self._streaming_pull_future = None
        if (subscriber := self._subscriber) is not None:
            with contextlib.suppress(Exception):
                await asyncio.to_thread(subscriber.close)
            self._subscriber = None
        self._mark_disconnected()
        logger.info("[GoogleChat] Disconnected")

    async def _run_supervisor(self) -> None:
        """Run streaming_pull with exponential backoff + full jitter; fatal after N attempts.
        ``subscribe()`` returns a Future that resolves when the stream dies."""
        pubsub_fatals = {
            gax_exceptions.Unauthenticated: ("pubsub_auth", "Pub/Sub authentication failed (SA key invalid/revoked)"),
            gax_exceptions.PermissionDenied: ("pubsub_permission", "SA lacks pubsub.subscriber on the subscription"),
        }
        attempt = 0
        while not self._shutting_down:
            flow = pubsub_v1.types.FlowControl(max_messages=self._max_messages, max_bytes=self._max_bytes)
            try:
                self._streaming_pull_future = future = self._subscriber.subscribe(
                    self._subscription_path, callback=self._on_pubsub_message, flow_control=flow)
                if attempt > 0:
                    logger.info("[GoogleChat] Pub/Sub stream reconnected after %d attempts", attempt)
                attempt = 0
                # Blocks until stream dies or cancel(); normal completion = disconnect.
                await asyncio.to_thread(future.result)
                if self._shutting_down:
                    return
            except asyncio.CancelledError:
                return
            except (gax_exceptions.Unauthenticated, gax_exceptions.PermissionDenied) as exc:
                code, message = pubsub_fatals[type(exc)]
                self._set_fatal_error(code=code, message=message, retryable=False)
                return
            except Exception as exc:
                attempt += 1
                logger.warning("[GoogleChat] Pub/Sub stream died (attempt %d/%d): %s", attempt,
                               self._MAX_RECONNECT_ATTEMPTS, _redact_sensitive(str(exc)))
                if attempt >= self._MAX_RECONNECT_ATTEMPTS:
                    self._set_fatal_error(
                        code="pubsub_reconnect_exhausted", message=f"Pub/Sub reconnect failed {attempt} times; giving up",
                        retryable=False,
                    )
                    return
                delay = min(self._RECONNECT_MAX_DELAY, self._RECONNECT_BASE_DELAY * (2 ** (attempt - 1)))
                try:
                    await asyncio.sleep(random.uniform(0, delay))
                except asyncio.CancelledError:
                    return

    # -- inbound (Pub/Sub callback runs in a thread) -------------------------
    @staticmethod
    def _extract_message_payload(envelope: Dict[str, Any],
                                 ce_type: str = "") -> Optional[Tuple[Dict[str, Any], Dict[str, Any], str]]:
        """Return ``(message, space, format_name)`` or None for unknown / non-MESSAGE
        envelopes. Formats: Workspace Add-ons ``{"chat": {"messagePayload": ...}}``; native
        ``{"type": "MESSAGE", "message", "space"}``; relay/flat ``{"event_type", "sender_email",
        "text", ...}`` (a Chat-shaped ``message`` is synthesized)."""
        msg_payload_wrapper = (envelope.get("chat") or {}).get("messagePayload")
        if msg_payload_wrapper:
            msg = msg_payload_wrapper.get("message") or {}
            return msg, msg_payload_wrapper.get("space") or msg.get("space") or {}, "workspace_addons"
        if isinstance(envelope.get("message"), dict):
            if envelope.get("type", "") != "MESSAGE":
                return None
            msg = envelope["message"]
            return msg, envelope.get("space") or msg.get("space") or {}, "native_chat_api"
        if "event_type" in envelope or "sender_email" in envelope:
            if envelope.get("event_type", "MESSAGE") != "MESSAGE":
                return None
            sender_email = (envelope.get("sender_email") or "").strip()
            text = envelope.get("text", "") or ""
            # Honor the relay's ``sender_type`` so the BOT self-filter fires for
            # forwarded bot replies; default HUMAN for backward compatibility.
            sender_type = str(envelope.get("sender_type") or "HUMAN").strip().upper()
            msg: Dict[str, Any] = {
                "name": envelope.get("message_name", "") or "",
                "sender": {
                    # No Chat resource name for relay events: a stable surrogate keeps dedup/session ids deterministic.
                    "name": "users/relay-" + (sender_email or "unknown").replace("@", "_at_").replace(".", "_"),
                    "email": sender_email, "displayName": envelope.get("sender_display_name") or sender_email or "Unknown",
                    "type": sender_type if sender_type in {"HUMAN", "BOT"} else "HUMAN",
                },
                "text": text, "argumentText": text,
            }
            if envelope.get("thread_name"):
                msg["thread"] = {"name": envelope["thread_name"]}
            space = {"name": envelope.get("space_name", "") or "", "spaceType": envelope.get("space_type", "SPACE")}
            return msg, space, "relay_flat"
        return None

    def _prepare_inbound(self, envelope: Dict[str, Any],
                         ce_type: Optional[str] = None) -> Optional[Tuple[Dict[str, Any], Dict[str, Any]]]:
        """Extract + self-filter + dedup an inbound envelope. Returns ``(msg_with_space,
        enriched_envelope)`` for ``_dispatch_message``, or None when the event must be
        dropped. Debug logs only on the Pub/Sub path (``ce_type`` given)."""
        extracted = self._extract_message_payload(envelope, ce_type or "")
        if extracted is None:
            if ce_type is not None:
                logger.debug(
                    "[GoogleChat] Envelope did not match a known message format; ce-type=%s, keys=%s",
                    ce_type, list(envelope.keys()),
                )
            return None
        msg, space, _fmt = extracted
        # Self-filter: drop bot-sourced messages (own replies and other bots).
        if (msg.get("sender") or {}).get("type") == "BOT":
            return None
        # Dedup guard — Pub/Sub is at-least-once.
        msg_name = msg.get("name") or ""
        if msg_name and self._dedup.is_duplicate(msg_name):
            if ce_type is not None:
                logger.debug("[GoogleChat] Dedup drop for %s", msg_name)
            return None
        # Give both dicts a top-level "space" so the dispatch side has one shape.
        msg_with_space, enriched_env = dict(msg), dict(envelope)
        for d in (msg_with_space, enriched_env):
            if "space" not in d and space:
                d["space"] = space
        return msg_with_space, enriched_env

    def _on_pubsub_message(self, message: Any) -> None:
        """Pub/Sub callback — parse envelope and dispatch to the asyncio loop.
        Runs in a SubscriberClient worker thread: never block, never raise (that
        triggers nack + infinite redelivery). Event type comes from ``ce-type``."""
        if self._shutting_down:
            message.nack()
            return
        try:
            envelope = json.loads(message.data.decode("utf-8"))
        except Exception:
            logger.exception("[GoogleChat] Could not parse Pub/Sub envelope")
            message.ack()
            return
        ce_type = dict(getattr(message, "attributes", {}) or {}).get("ce-type") or ""
        logger.debug("[GoogleChat] Envelope keys=%s, ce-type=%s", list(envelope.keys()), ce_type)
        if self._debug_raw:
            # Contains message text + sender email: redact and gate at DEBUG.
            try:
                from agent.redact import redact_sensitive_text
                dump = redact_sensitive_text(json.dumps(envelope))
            except Exception:
                dump = "<redact filter unavailable>"
            logger.debug("[GoogleChat] RAW envelope (redacted): %s", dump[:2000])
        try:
            if "membership" in ce_type or "MEMBERSHIP" in ce_type:
                mpl = (envelope.get("chat") or {}).get("membershipPayload") or {}
                space = mpl.get("space") or {}
                if "created" in ce_type:
                    # ADDED_TO_SPACE for this bot — resolve self user_id.
                    member = (mpl.get("membership") or {}).get("member") or {}
                    if member.get("type") == "BOT" and not self._bot_user_id and member.get("name"):
                        self._bot_user_id = member["name"]
                        self._save_cached_bot_id(member["name"])
                    logger.info("[GoogleChat] ADDED_TO_SPACE %s", space.get("name", "?"))
                else:
                    logger.info("[GoogleChat] REMOVED_FROM_SPACE %s", space.get("name", "?"))
            elif "widget" in ce_type or "card" in ce_type.lower():
                logger.info("[GoogleChat] Card/widget event ack'd (v2 feature, deferred)")
            else:
                prepared = self._prepare_inbound(envelope, ce_type)
                if prepared is not None:
                    self._submit_on_loop(self._dispatch_message(*prepared))
            message.ack()
        except Exception:
            logger.exception("[GoogleChat] Error in _on_pubsub_message")
            with contextlib.suppress(Exception):
                message.ack()

    async def dispatch_http_event(self, envelope: Dict[str, Any]) -> Dict[str, Any]:
        prepared = self._prepare_inbound(envelope)
        if prepared is not None:
            await self._dispatch_message(*prepared)
        return {}

    def verify_http_event_request(self, auth_header: str) -> Tuple[bool, str]:
        if not self._http_events_audience or not self._http_events_service_account_email:
            return False, "google_chat_http_events_not_configured"
        token = auth_header[7:].strip() if auth_header.startswith("Bearer ") else ""
        if not token:
            return False, "missing_google_bearer"
        try:
            claims = _verify_google_id_token(token, self._http_events_audience)
        except Exception as exc:
            logger.warning("[GoogleChat] HTTP event bearer verification failed: %s", _redact_sensitive(str(exc)))
            return False, "invalid_google_bearer"
        expected = {item.strip().lower() for item in self._http_events_service_account_email.split(",") if item.strip()}
        if str(claims.get("email") or "").strip().lower() not in expected:
            return False, "unexpected_google_bearer_identity"
        return True, ""

    async def _dispatch_message(self, msg: Dict[str, Any], envelope: Dict[str, Any]) -> None:
        """Translate a Chat message to a MessageEvent and hand off.
        ``/setup-files`` is intercepted BEFORE the agent sees it (bot-local OAuth flow)."""
        try:
            event = await self._build_message_event(msg, envelope)
            if event is None:
                return
            text = (event.text or "").strip()
            # The sender email (user_id_alt) is the per-user OAuth token key.
            if text.startswith("/setup-files") and event.source is not None and await self._handle_setup_files_command(
                chat_id=event.source.chat_id, thread_id=event.source.thread_id, raw_text=text,
                sender_email=event.source.user_id_alt or None,
            ):
                return
            await self.handle_message(event)
        except Exception:
            logger.exception("[GoogleChat] _dispatch_message failed")

    async def _handle_setup_files_command(self, chat_id: str, thread_id: Optional[str], raw_text: str,
                                          sender_email: Optional[str] = None) -> bool:
        """In-chat OAuth setup flow; see ``setup_files.handle_setup_files_command``."""
        from .setup_files import handle_setup_files_command
        return await handle_setup_files_command(self, chat_id, thread_id, raw_text, sender_email)

    async def _build_message_event(self, msg: Dict[str, Any], envelope: Dict[str, Any]) -> Optional[MessageEvent]:
        """Parse a Chat API message into a hermes MessageEvent."""
        space = envelope.get("space") or msg.get("space") or {}
        space_name = space.get("name") or ""  # "spaces/XXX"
        space_type = (space.get("type") or space.get("spaceType") or "").upper()
        thread_name = (msg.get("thread") or {}).get("name") or None
        sender = msg.get("sender") or {}
        sender_name = sender.get("name") or ""
        sender_email = sender.get("email") or ""
        # Cache the asker's email per space so _send_file picks the right per-user
        # OAuth token (lower-cased to match the sanitized token-file lookup).
        if sender_email and space_name:
            self._last_sender_by_chat[space_name] = sender_email.strip().lower()
        chat_type = "dm" if space_type in {"DIRECT_MESSAGE", "DM"} else "group"
        text = (msg.get("argumentText") or msg.get("text") or "").strip()
        # Slash command: emit MessageType.COMMAND with normalized text.
        slash = msg.get("slashCommand") or {}
        if slash:
            command_id = str(slash.get("commandId") or "")
            if command_id and not text.startswith("/"):
                text = f"/cmd_{command_id} {text}".strip()

        media_urls: List[str] = []
        media_types: List[str] = []
        message_type = MessageType.TEXT
        for att in msg.get("attachment") or []:
            try:
                local_path, mime = await self._download_attachment(att)
            except Exception:
                logger.exception("[GoogleChat] attachment download failed")
                continue
            if not local_path:
                continue
            media_urls.append(local_path)
            media_types.append(mime or "application/octet-stream")
            # Prefer the first-seen type for MessageType if no text present.
            if message_type == MessageType.TEXT and not text:
                message_type = _mime_for_message_type(mime or "")
        if slash:
            message_type = MessageType.COMMAND

        # PRE-increment count (persisted) drives the main-flow-vs-side-thread heuristic.
        prev_thread_count = self._thread_count_store.incr(space_name, thread_name) if thread_name and space_name else 0
        # DMs: prev_count == 0 → Chat auto-created this thread for a top-level message: share one
        # DM session, reply top-level (thread.name would render an expandable thread); >= 1 → user
        # engaged an existing thread: isolate + reply in-thread. Groups: always isolate + in-thread.
        if chat_type == "dm":
            is_side_thread = prev_thread_count > 0
            session_thread_id = thread_name if is_side_thread else None
            # Outbound cache only for side-threads so main-flow replies land top-level.
            if thread_name and space_name and is_side_thread:
                self._last_inbound_thread[space_name] = thread_name
            elif space_name:
                self._last_inbound_thread.pop(space_name, None)
        else:
            session_thread_id = thread_name
            if thread_name and space_name:
                self._last_inbound_thread[space_name] = thread_name
        source = self.build_source(
            chat_id=space_name, chat_name=space.get("displayName") or space.get("name") or "", chat_type=chat_type,
            # Email is the canonical id (allowlists use emails); the ``users/{id}``
            # resource name moves to user_id_alt.
            user_id=(sender_email or sender_name), user_name=sender.get("displayName") or sender_email or sender_name,
            thread_id=session_thread_id, user_id_alt=(sender_name or None), message_id=msg.get("name") or None,
        )
        return MessageEvent(
            text=text, message_type=message_type, source=source, raw_message=msg, message_id=msg.get("name") or None,
            media_urls=media_urls, media_types=media_types,
        )

    async def _download_attachment(self, attachment: Dict[str, Any]) -> Tuple[Optional[str], Optional[str]]:
        """Download an inbound attachment to the local cache; return (path, mime). Bot SA
        path is ``media.download`` via ``attachmentDataRef.resourceName``; Drive-picker shares
        without one need user OAuth (skipped); ``downloadUri`` is a last resort (usually 401s)."""
        mime = attachment.get("contentType") or ""
        name = attachment.get("name") or ""
        resource_name = (attachment.get("attachmentDataRef") or {}).get("resourceName") or ""
        download_uri = attachment.get("downloadUri") or ""
        # Chat tags BOTH drag-and-drop uploads AND Drive-picker shares as DRIVE_FILE;
        # only the former carry a resourceName the bot path can use.
        if (attachment.get("source") or "") == "DRIVE_FILE" and not resource_name:
            logger.info("[GoogleChat] Skipping Drive-picker attachment (no resourceName, would need user-OAuth Drive scope)")
            return None, mime

        data: Optional[bytes] = None
        if resource_name:
            def _fetch_media() -> bytes:
                req = self._chat_api.media().download_media(resourceName=resource_name)
                from googleapiclient.http import MediaIoBaseDownload
                import io

                buf = io.BytesIO()
                downloader, done = MediaIoBaseDownload(buf, req), False
                while not done:
                    _status, done = downloader.next_chunk()
                return buf.getvalue()
            try:
                data = await asyncio.to_thread(_fetch_media)
            except HttpError as exc:
                logger.warning("[GoogleChat] media.download_media failed: %s", _redact_sensitive(str(exc)))
        if data is None and download_uri:
            if not _is_google_owned_host(download_uri):
                logger.warning("[GoogleChat] Rejecting attachment fetch: non-Google host")
                return None, mime

            def _fetch_uri() -> bytes:
                import google.auth.transport.requests as gar

                resp = gar.AuthorizedSession(self._credentials).get(download_uri, timeout=30)
                resp.raise_for_status()
                return resp.content
            try:
                data = await asyncio.to_thread(_fetch_uri)
            except Exception as exc:
                logger.warning(
                    "[GoogleChat] downloadUri fetch failed (SA tokens often lack access here; this is expected for "
                    "user-uploaded content): %s", _redact_sensitive(str(exc)),
                )
                return None, mime
        if data is None:
            return None, mime
        # cache_* helpers take ``ext`` for media and a positional filename for docs.
        filename = name.split("/")[-1] if name else "attachment"
        ext = "." + filename.rsplit(".", 1)[-1].lower() if "." in filename else ""
        for prefix, cache_fn, default_ext in _MEDIA_CACHERS:
            if mime.startswith(prefix):
                return await cache_fn(data, ext=ext or default_ext), mime
        return await cache_document_from_bytes_async(data, filename), mime

    # -- outbound ------------------------------------------------------------
    def _note_rate_limit(self, chat_id: str) -> int:
        self._rate_limit_hits[chat_id] = self._rate_limit_hits.get(chat_id, 0) + 1
        return self._rate_limit_hits[chat_id]

    async def send(self, chat_id: str, content: str, reply_to: Optional[str] = None,
                   metadata: Optional[Dict[str, Any]] = None) -> SendResult:
        """Send a text message; ``metadata`` may carry ``thread_id``. A tracked typing card is
        patched in place (delete would leave a "Message deleted" tombstone) with the first
        chunk, further chunks are new messages; ``_keep_typing`` is paused meanwhile."""
        thread_id = self._resolve_thread_id(reply_to, metadata, chat_id=chat_id)
        self.pause_typing_for_chat(chat_id)
        try:
            # Format BEFORE chunking so the size limit applies to the rendered form.
            chunks = self._chunk_text(self.format_message(content))
            if not chunks:
                return SendResult(success=False, error="empty message")
            last_result: Optional[SendResult] = None
            typing_msg_name = self._typing_messages.pop(chat_id, None)
            if typing_msg_name == _TYPING_CONSUMED_SENTINEL:
                typing_msg_name = None
            patched_typing = False
            for idx, chunk in enumerate(chunks):
                # Only set thread on the create path; patch inherits.
                body = _thread_body(chunk, thread_id if (idx > 0 or not typing_msg_name) else None)
                try:
                    if idx == 0 and typing_msg_name:
                        last_result = await self._patch_message(typing_msg_name, body)
                        patched_typing = True
                    else:
                        last_result = await self._create_message(chat_id, body)
                except HttpError as exc:
                    status = _http_status(exc)
                    if status == 403:
                        self._set_fatal_error(
                            code="chat_forbidden", message="Bot lacks access (removed from space or perms revoked)",
                            retryable=False,
                        )
                        return SendResult(success=False, error=str(exc))
                    if status == 404:
                        # Typing card deleted under us: fall back to a fresh message.
                        if idx == 0 and typing_msg_name:
                            logger.info("[GoogleChat] Typing card disappeared; creating new message")
                            typing_msg_name = None
                            last_result = await self._create_message(chat_id, body)
                            continue
                        logger.info("[GoogleChat] send target 404; skipping")
                        return SendResult(success=False, error="target not found")
                    if status == 429:
                        hits = self._note_rate_limit(chat_id)
                        if hits >= _RATE_LIMIT_WARN_THRESHOLD:
                            logger.warning("[GoogleChat] Rate limit hit %d times on chat; throttling", hits)
                    raise
            if last_result is None:
                return SendResult(success=False, error="empty message")
            # Sentinel keeps a trailing _keep_typing tick from posting a fresh marker that
            # stop_typing would then delete and tombstone. Cleared in on_processing_complete.
            if patched_typing:
                self._typing_messages[chat_id] = _TYPING_CONSUMED_SENTINEL
            return last_result
        finally:
            self.resume_typing_for_chat(chat_id)

    async def send_card(self, chat_id: str, card: Dict[str, Any], metadata: Optional[Dict[str, Any]] = None) -> SendResult:
        body: Dict[str, Any] = {"cardsV2": [card]}
        thread_id = self._resolve_thread_id(None, metadata, chat_id=chat_id)
        if thread_id:
            body["thread"] = {"name": thread_id}
        try:
            result = await self._create_message(chat_id, body)
            result.raw_response = result.raw_response or {"cardsV2": body["cardsV2"]}
            return result
        except HttpError as exc:
            return SendResult(
                success=False, error=_redact_sensitive(str(exc)), retryable=_http_status(exc) in _RETRYABLE_HTTP_STATUSES)
        except Exception as exc:
            logger.debug("[GoogleChat] send_card failed", exc_info=True)
            return SendResult(success=False, error=_redact_sensitive(str(exc)), retryable=_is_retryable_error(exc))

    async def send_clarify(
        self, chat_id: str, question: str, choices: Optional[list], clarify_id: str, session_key: str,
        metadata: Optional[Dict[str, Any]] = None,
    ) -> SendResult:
        if not choices:
            return await super().send_clarify(chat_id, question, choices, clarify_id, session_key, metadata)

        def _button(text: str, choice: str) -> Dict[str, Any]:
            return {"text": text, "action": "hermes_clarify", "parameters": {"clarify_id": clarify_id, "choice": choice}}
        buttons: List[Dict[str, Any]] = []
        for choice in choices:
            choice_text = str(choice).strip()
            if choice_text:
                buttons.append(_button(choice_text if len(choice_text) <= 80 else choice_text[:77] + "...", choice_text))
        buttons.append(_button("Other / type answer", "__other__"))
        card = card_spec_to_cards_v2({
            "card_id": f"clarify-{clarify_id}", "header": {"title": "Question"},
            "sections": [{"widgets": [{"type": "text", "text": f"❓ {question}"}, {"type": "buttons", "buttons": buttons}]}],
        })
        result = await self.send_card(chat_id, card, metadata=metadata)
        if result.success:
            self._clarify_state[clarify_id] = session_key
            return result
        return await super().send_clarify(chat_id, question, choices, clarify_id, session_key, metadata)

    async def edit_message(self, chat_id: str, message_id: str, content: str, *, finalize: bool = False) -> SendResult:
        """Edit via ``messages.patch`` (required by the tool-progress / token-streaming
        pipeline). ``finalize`` is unused: Chat's patch has no streaming lifecycle.
        404/403 are non-success so the gateway falls back to ``send()``."""
        if not message_id:
            return SendResult(success=False, error="missing message_id")
        if len(content) > _MAX_TEXT_LENGTH:
            content = content[: _MAX_TEXT_LENGTH - 1] + "…"
        try:
            return await self._patch_message(message_id, {"text": content})
        except HttpError as exc:
            if _http_status(exc) == 429:
                self._note_rate_limit(chat_id)
            return SendResult(success=False, error=_redact_sensitive(str(exc)))
        except Exception as exc:
            logger.debug("[GoogleChat] edit_message failed", exc_info=True)
            return SendResult(success=False, error=str(exc))

    async def delete_message(self, chat_id: str, message_id: str) -> bool:
        """Delete a message. Prefer ``edit_message`` — deletion leaves a "Message
        deleted by its author" tombstone; kept for stream-consumer fallback paths."""
        if not message_id:
            return False

        try:
            await asyncio.to_thread(
                lambda: self._chat_api.spaces().messages().delete(name=message_id).execute(http=self._new_authed_http()))
            return True
        except HttpError as exc:
            if _http_status(exc) not in {403, 404}:
                logger.debug("[GoogleChat] delete_message failed: %s", _redact_sensitive(str(exc)))
        except Exception:
            logger.debug("[GoogleChat] delete_message failed", exc_info=True)
        return False

    async def _patch_message(self, message_name: str, body: Dict[str, Any]) -> SendResult:
        """Update a message's text (and optionally cards) in-place."""
        update_mask = ",".join(k for k in ("text", "cardsV2") if k in body) or "text"
        patch_body = {k: v for k, v in body.items() if k != "thread"}  # thread is immutable
        resp = await asyncio.to_thread(
            lambda: self._chat_api.spaces().messages().patch(name=message_name, updateMask=update_mask, body=patch_body)
            .execute(http=self._new_authed_http())
        )
        return SendResult(success=True, message_id=resp.get("name", message_name))

    def _chunk_text(self, text: str) -> List[str]:
        chunks: List[str] = []
        remaining = text
        while remaining:
            if len(remaining) <= _MAX_TEXT_LENGTH:
                chunks.append(remaining)
                break
            # Split on a newline near the cutoff when one exists past the midpoint.
            cut = remaining.rfind("\n", 0, _MAX_TEXT_LENGTH)
            if cut < _MAX_TEXT_LENGTH // 2:
                cut = _MAX_TEXT_LENGTH
            chunks.append(remaining[:cut])
            remaining = remaining[cut:].lstrip()
        return chunks

    @classmethod
    def format_message(cls, content: str) -> str:
        """Convert standard Markdown to Google Chat's dialect (see ``cards.format_message``).

        Pattern lifted from PR #14965.
        """
        return _format_message(content)

    def _resolve_thread_id(self, reply_to: Optional[str], metadata: Optional[Dict[str, Any]],
                           chat_id: Optional[str] = None) -> Optional[str]:
        """Thread to reply under, or None: ``metadata['thread_id']`` → ``thread_name`` /
        ``thread_ts`` aliases → ``reply_to`` when already a ``spaces/X/threads/Y`` name →
        ``_last_inbound_thread[chat_id]`` (else DM replies land top-level). Cron deliveries
        (``job_id`` in metadata) skip the last fallback so output is not buried in a stale thread."""
        if metadata:
            for key in ("thread_id", "thread_name", "thread_ts"):
                if metadata.get(key):
                    return str(metadata[key])
        if reply_to and "/threads/" in reply_to and "/messages/" not in reply_to:
            return reply_to
        if metadata and metadata.get("job_id"):
            return None
        return (self._last_inbound_thread.get(chat_id) or None) if chat_id else None

    def _new_authed_http(self) -> Any:
        """Fresh AuthorizedHttp per call: httplib2 shares SSL state, so the discovery
        client is not thread-safe across ``asyncio.to_thread`` workers."""
        return AuthorizedHttp(self._credentials, http=httplib2.Http(timeout=30))

    async def _call_with_retry(self, sync_fn: Callable[[], Any], *, op_name: str = "chat-api-call") -> Any:
        """Run ``sync_fn`` in a thread with bounded retry + jittered backoff; only
        transient failures are retried, permanent ones bubble up on the first attempt.

        Pattern lifted from PR #14965.
        """
        delay = _RETRY_BASE_DELAY
        for attempt in range(1, _RETRY_MAX_ATTEMPTS + 1):
            try:
                return await asyncio.to_thread(sync_fn)
            except Exception as exc:
                if not _is_retryable_error(exc) or attempt >= _RETRY_MAX_ATTEMPTS:
                    raise
                wait = min(delay + delay * _RETRY_JITTER * random.random(), _RETRY_MAX_DELAY + _RETRY_JITTER)
                logger.warning(
                    "[GoogleChat] %s attempt %d/%d failed (%s); retrying in %.2fs",
                    op_name, attempt, _RETRY_MAX_ATTEMPTS, _redact_sensitive(str(exc)), wait,
                )
                await asyncio.sleep(wait)
                delay = min(delay * 2, _RETRY_MAX_DELAY)

    def _track_outbound_thread(self, chat_id: str, resp: Dict[str, Any]) -> None:
        """Count the outbound destination thread so a later user "Reply in thread" on
        the bot's message resolves as a known side-thread instead of main flow."""
        resp_thread = (resp.get("thread") or {}).get("name") or ""
        if chat_id and resp_thread:
            try:
                self._thread_count_store.incr(chat_id, resp_thread)
            except Exception:
                logger.debug("[GoogleChat] outbound thread-count incr failed", exc_info=True)

    async def _create_message(self, chat_id: str, body: Dict[str, Any]) -> SendResult:
        """POST spaces/{space}/messages via REST (with retry), returning SendResult."""
        kwargs = _create_kwargs(chat_id, body)
        resp = await self._call_with_retry(
            lambda: self._chat_api.spaces().messages().create(**kwargs).execute(http=self._new_authed_http()),
            op_name="messages.create",
        )
        self._track_outbound_thread(chat_id, resp)
        return SendResult(success=True, message_id=resp.get("name"))

    async def send_typing(self, chat_id: str, metadata: Any = None) -> None:
        """Post a visible 'Hermes is thinking…' marker (Chat has no typing API); ``send()``
        PATCHes it with the reply, ``on_processing_complete`` reaps it otherwise. Created in
        the user's thread (patch cannot move it). ``_keep_typing`` wraps this in
        ``wait_for(timeout=1.5)``: a cancelled create would still land an unrecorded card and
        the next tick would create a second, so the slot is reserved with an in-flight Event
        and the create runs in a shielded task that records the msg_id regardless."""
        # Already have a card (real msg_id, sentinel, or in-flight) — bail.
        if chat_id in self._typing_messages:
            return
        if chat_id in self._typing_card_inflight:
            # Bounded wait for the running create so "the card is up when we return".
            with contextlib.suppress(asyncio.TimeoutError, KeyError):
                await asyncio.wait_for(self._typing_card_inflight[chat_id].wait(), timeout=5.0)
            return
        thread_id = self._resolve_thread_id(reply_to=None, metadata=metadata, chat_id=chat_id)
        body = _thread_body(getattr(self.config, "typing_status_text", None) or "Hermes is thinking…", thread_id)
        self._typing_card_inflight[chat_id] = completed = asyncio.Event()

        async def _create_and_record() -> None:
            try:
                result = await self._create_message(chat_id, body)
                if result.success and result.message_id:
                    if chat_id not in self._typing_messages:
                        self._typing_messages[chat_id] = result.message_id
                    else:
                        # send() or another create claimed the slot first: orphan;
                        # on_processing_complete cleans it up.
                        self._orphan_typing_messages.setdefault(chat_id, []).append(result.message_id)
            except Exception:
                logger.debug("[GoogleChat] send_typing background create failed", exc_info=True)
            finally:
                self._typing_card_inflight.pop(chat_id, None)
                completed.set()

        # The shielded task keeps running if our awaiter is cancelled.
        await asyncio.shield(asyncio.create_task(_create_and_record()))

    async def stop_typing(self, chat_id: str) -> None:
        """NO-OP for a live card: upstream calls ``stop_typing`` BEFORE ``send()`` patches it
        (deleting would tombstone). Only the SENTINEL is popped so the next turn starts clean;
        stranded cards are reaped by ``on_processing_complete``."""
        if self._typing_messages.get(chat_id) == _TYPING_CONSUMED_SENTINEL:
            self._typing_messages.pop(chat_id, None)

    async def _patch_quietly(self, message_name: str, text: str, log_msg: str, *log_args: Any) -> None:
        try:
            await self._patch_message(message_name, {"text": text})
        except Exception:
            logger.debug(log_msg, *log_args, exc_info=True)

    async def on_processing_complete(self, event: MessageEvent, outcome: ProcessingOutcome) -> None:
        """Reap typing card(s) after the turn: pop the SENTINEL on success; on
        failure/cancel patch a still-tracked card to a final label (no tombstone);
        patch orphan cards (background creates that lost a race with send()) to "·"."""
        if event.source is None:
            return
        chat_id = event.source.chat_id
        try:
            current = self._typing_messages.pop(chat_id, None)
            if current and current != _TYPING_CONSUMED_SENTINEL:
                label = "(interrupted)" if outcome == ProcessingOutcome.CANCELLED else "(no reply)"
                await self._patch_quietly(current, label, "[GoogleChat] on_processing_complete patch fallback failed")
            for orphan_id in self._orphan_typing_messages.pop(chat_id, []):
                await self._patch_quietly(orphan_id, "·", "[GoogleChat] orphan typing-card patch failed: %s", orphan_id)
        except Exception:
            logger.debug("[GoogleChat] cleanup in on_processing_complete failed", exc_info=True)

    # -- attachments ---------------------------------------------------------
    async def _consume_typing_card_with_text(self, chat_id: str, text: str) -> Optional[SendResult]:
        """Patch the tracked typing card with ``text`` (no tombstone); None when there is no
        real card (caller creates a message) — the SENTINEL stays so ``_keep_typing`` doesn't
        post a fresh card during a subsequent attachment send. Raises transient HttpErrors."""
        current = self._typing_messages.get(chat_id)
        if not current or current == _TYPING_CONSUMED_SENTINEL:
            return None
        self._typing_messages.pop(chat_id, None)
        try:
            result = await self._patch_message(current, {"text": text})
            self._typing_messages[chat_id] = _TYPING_CONSUMED_SENTINEL
            return result
        except HttpError as exc:
            if _http_status(exc) == 404:
                return None  # card disappeared — caller creates a new message
            raise

    async def send_image(
        self, chat_id: str, image_url: str, caption: Optional[str] = None, reply_to: Optional[str] = None,
        metadata: Optional[Dict[str, Any]] = None,
    ) -> SendResult:
        """Send an inline image via URL (no upload); patches the typing card when tracked."""
        thread_id = self._resolve_thread_id(reply_to, metadata, chat_id=chat_id)
        text = "\n".join(([caption] if caption else []) + [image_url])
        try:
            patched = await self._consume_typing_card_with_text(chat_id, text)
            if patched is not None:
                return patched
            return await self._create_message(chat_id, _thread_body(text, thread_id))
        except HttpError as exc:
            return SendResult(success=False, error=_redact_sensitive(str(exc)))

    async def _send_file_reply(
        self, chat_id: str, path: str, caption: Optional[str], reply_to: Optional[str], kwargs: Dict[str, Any],
        mime_hint: Optional[str], override_filename: Optional[str] = None,
    ) -> SendResult:
        thread_id = self._resolve_thread_id(reply_to, kwargs.get("metadata"), chat_id=chat_id)
        return await self._send_file(
            chat_id, path, caption, mime_hint=mime_hint, thread_id=thread_id, override_filename=override_filename)

    async def send_image_file(self, chat_id: str, image_path: str, caption: Optional[str] = None,
                              reply_to: Optional[str] = None, **kwargs: Any) -> SendResult:
        return await self._send_file_reply(chat_id, image_path, caption, reply_to, kwargs, "image/*")

    async def send_document(
        self, chat_id: str, file_path: str, caption: Optional[str] = None, file_name: Optional[str] = None,
        reply_to: Optional[str] = None, **kwargs: Any,
    ) -> SendResult:
        return await self._send_file_reply(chat_id, file_path, caption, reply_to, kwargs, None, file_name)

    async def send_voice(self, chat_id: str, audio_path: str, caption: Optional[str] = None,
                         reply_to: Optional[str] = None, **kwargs: Any) -> SendResult:
        return await self._send_file_reply(chat_id, audio_path, caption, reply_to, kwargs, "audio/ogg")

    async def send_video(self, chat_id: str, video_path: str, caption: Optional[str] = None,
                         reply_to: Optional[str] = None, **kwargs: Any) -> SendResult:
        return await self._send_file_reply(chat_id, video_path, caption, reply_to, kwargs, "video/mp4")

    async def send_animation(
        self, chat_id: str, animation_url: str, caption: Optional[str] = None, reply_to: Optional[str] = None,
        metadata: Optional[Dict[str, Any]] = None,
    ) -> SendResult:
        """Google Chat has no native animation type; fall back to send_image."""
        return await self.send_image(chat_id, animation_url, caption=caption, reply_to=reply_to, metadata=metadata)

    # -- native attachment delivery via user OAuth: media.upload hard-rejects SA
    # auth, so the user grants chat.messages.create ONCE via ``/setup-files`` and
    # the bot uploads AS the user (see ``oauth.py``). --------------------------
    @staticmethod
    async def _refresh_or_none(creds: Any, email: Optional[str], log_msg: str) -> Optional[Any]:
        """``oauth.refresh_or_none`` in a thread; a raise is logged at DEBUG and treated as None."""
        from .oauth import refresh_or_none as _refresh
        try:
            return await asyncio.to_thread(_refresh, creds, email)
        except Exception:
            logger.debug(log_msg, exc_info=True)
            return None

    async def _load_per_user_chat_api(self, email: str) -> Optional[Any]:
        """Get (or build + cache) a user-authed Chat client for ``email``.
        Cache hit → refresh creds (evict on failure so the next request goes back
        through disk / the text-notice fallback). Miss → load token, build, cache."""
        from .oauth import load_user_credentials as _load, build_user_chat_service as _build
        cached_api = self._user_chat_api_by_email.get(email)
        cached_creds = self._user_creds_by_email.get(email)
        if cached_api is not None and cached_creds is not None:
            refreshed = await self._refresh_or_none(cached_creds, email, "[GoogleChat] cached per-user refresh raised")
            if refreshed is None:
                self._invalidate_user_creds(email)
                return None
            self._user_creds_by_email[email] = refreshed
            return cached_api
        try:
            creds = await asyncio.to_thread(_load, email)
            if creds is None:
                return None
            api = await asyncio.to_thread(lambda: _build(creds))
        except Exception:
            logger.debug("[GoogleChat] per-user creds load/build failed for %s", email, exc_info=True)
            return None
        self._user_creds_by_email[email] = creds
        self._user_chat_api_by_email[email] = api
        return api

    async def _acquire_user_chat_api(self, sender_email: Optional[str]) -> Tuple[Optional[Any], Optional[str]]:
        """User-authed Chat client for an outbound attachment: per-user token for
        ``sender_email`` → legacy single-user fallback → ``(None, None)`` (caller posts the
        setup notice). The identity label (email / ``"__legacy__"``) selects the slot to evict."""
        if sender_email:
            api = await self._load_per_user_chat_api(sender_email)
            if api is not None:
                return api, sender_email
        if self._user_chat_api is not None:
            refreshed = await self._refresh_or_none(self._user_credentials, None, "[GoogleChat] legacy creds refresh raised")
            if refreshed is None:
                logger.warning("[GoogleChat] legacy user-OAuth refresh returned None — evicting fallback creds")
                self._invalidate_user_creds(self._LEGACY_USER_IDENTITY)
                return None, None
            self._user_credentials = refreshed
            return self._user_chat_api, self._LEGACY_USER_IDENTITY
        return None, None

    def _invalidate_user_creds(self, identity: Optional[str]) -> None:
        """Drop creds for ``identity`` (email or ``__legacy__``) after an auth failure."""
        if not identity:
            return
        if identity == self._LEGACY_USER_IDENTITY:
            self._user_credentials = self._user_chat_api = None
            return
        self._user_creds_by_email.pop(identity, None)
        self._user_chat_api_by_email.pop(identity, None)

    async def _send_file(
        self, chat_id: str, path: str, caption: Optional[str], mime_hint: Optional[str],
        thread_id: Optional[str] = None, override_filename: Optional[str] = None,
    ) -> SendResult:
        """Native attachment: user-authed ``media.upload`` then ``messages.create`` with the
        latest inbound sender's token (legacy token as fallback; text notice when neither).
        ``messages.patch`` cannot add attachments, so the typing card is patched with the
        caption (or a single space) to retire it without a tombstone."""
        if not os.path.exists(path):
            return SendResult(success=False, error=f"file not found: {path}")
        filename = override_filename or os.path.basename(path) or "upload.bin"
        mime = mime_hint or "application/octet-stream"
        chat_api, identity = await self._acquire_user_chat_api(self._last_sender_by_chat.get(chat_id))
        if chat_api is None:
            return await self._post_attachment_fallback(chat_id, path, filename, caption, thread_id)
        try:
            await self._consume_typing_card_with_text(chat_id, caption or " ")
        except Exception:
            logger.debug("[GoogleChat] _send_file pre-patch typing-card failed", exc_info=True)

        try:
            upload_resp = await asyncio.to_thread(lambda: chat_api.media().upload(
                parent=chat_id, body={"filename": filename},
                media_body=MediaFileUpload(path, mimetype=mime, resumable=False),
            ).execute())
        except HttpError as exc:
            status = _http_status(exc)
            if status in {401, 403}:
                logger.warning(
                    "[GoogleChat] media.upload auth failure for identity=%s (token revoked or scope missing) — falling "
                    "back to text notice. Status=%s", identity, status,
                )
                self._invalidate_user_creds(identity)
                return await self._post_attachment_fallback(chat_id, path, filename, caption, thread_id)
            return SendResult(success=False, error=_redact_sensitive(str(exc)))
        attachment_ref = upload_resp.get("attachmentDataRef")
        if not attachment_ref:
            return SendResult(success=False, error="upload returned no attachmentDataRef")
        body: Dict[str, Any] = {"attachment": [{"attachmentDataRef": attachment_ref}]}
        body.update({k: v for k, v in (("text", caption), ("thread", {"name": thread_id} if thread_id else None)) if v})
        # The attachmentDataRef is bound to the uploading principal, so this create
        # also needs user auth.
        create_kwargs = _create_kwargs(chat_id, body)
        try:
            resp = await asyncio.to_thread(lambda: chat_api.spaces().messages().create(**create_kwargs).execute())
            self._track_outbound_thread(chat_id, resp)
            return SendResult(success=True, message_id=resp.get("name"))
        except HttpError as exc:
            return SendResult(success=False, error=_redact_sensitive(str(exc)))

    async def _post_attachment_fallback(self, chat_id: str, path: str, filename: str, caption: Optional[str],
                                        thread_id: Optional[str]) -> SendResult:
        """Post the ``/setup-files`` notice (plus host path) when native delivery is
        unavailable. Always returns ``success=False``."""
        lines = [caption] if caption else []
        lines.extend([
            f"⚠️ No he podido adjuntar **{filename}**.",
            "Google Chat sólo permite adjuntar archivos cuando el bot tiene permiso explícito tuyo (OAuth de usuario). "
            "Es un consentimiento único que se hace desde este chat.",
            "**Para activarlo:** envía `/setup-files` y sigue las instrucciones.",
            f"Mientras tanto el archivo está en el host: `{path}`",
        ])
        try:
            await self._create_message(chat_id, _thread_body("\n".join(lines), thread_id))
        except Exception:
            logger.debug("[GoogleChat] attachment fallback notice send failed", exc_info=True)
        return SendResult(
            success=False, error="google_chat: native attachment requires user OAuth — run /setup-files in chat")

    async def get_chat_info(self, chat_id: str) -> Dict[str, Any]:
        """Return {name, type, chat_id} for a space."""
        try:
            info = await asyncio.to_thread(
                lambda: self._chat_api.spaces().get(name=chat_id).execute(http=self._new_authed_http()))
        except HttpError as exc:
            logger.debug("[GoogleChat] get_chat_info failed: %s", _redact_sensitive(str(exc)))
            return {"name": chat_id, "type": "group", "chat_id": chat_id}
        space_type = (info.get("spaceType") or info.get("type") or "").upper()
        return {
            "name": info.get("displayName") or chat_id,
            "type": "dm" if space_type in {"DIRECT_MESSAGE", "DM"} else "group",
            "chat_id": chat_id,
        }


# -- plugin entry point -----------------------------------------------------
def _validate_config(config: PlatformConfig) -> bool:
    """Plugin-side config gate for HTTP callback or Pub/Sub inbound modes."""
    extra = getattr(config, "extra", {}) or {}
    return bool(extra.get("http_events_url") or (extra.get("project_id") and extra.get("subscription_name")))


def _env_inbound_settings() -> Tuple[Optional[str], Optional[str], Optional[str]]:
    """(project, subscription, http_events_url) from the scoped env, with legacy fallbacks."""
    project = _get_scoped_secret("GOOGLE_CHAT_PROJECT_ID") or _get_scoped_secret("GOOGLE_CLOUD_PROJECT")
    subscription = _get_scoped_secret("GOOGLE_CHAT_SUBSCRIPTION_NAME") or _get_scoped_secret("GOOGLE_CHAT_SUBSCRIPTION")
    return project, subscription, _get_scoped_secret("GOOGLE_CHAT_HTTP_EVENTS_URL")


def _env_inbound_configured() -> bool:
    project, subscription, http_events_url = _env_inbound_settings()
    return bool(http_events_url or (project and subscription))


def _check_for_registry() -> bool:
    """``check_fn`` for the registry pass: deps installed AND minimum inbound env set,
    so an unconfigured user never sees ``google_chat`` auto-enabled."""
    return check_google_chat_requirements() and _env_inbound_configured()


def _is_connected(config: PlatformConfig) -> bool:
    """``GatewayConfig.get_connected_platforms()`` polls this."""
    return bool(getattr(config, "enabled", False)) and _validate_config(config)


_ENV_SEED_KEYS = (  # (env var, extra key, conv) for seed_extra_from_env
    ("GOOGLE_CHAT_HTTP_EVENTS_AUDIENCE", "http_events_audience", None),
    ("GOOGLE_CHAT_HTTP_EVENTS_SERVICE_ACCOUNT_EMAIL", "http_events_service_account_email", None),
    ("GOOGLE_CHAT_MAX_MESSAGES", "max_messages", None), ("GOOGLE_CHAT_MAX_BYTES", "max_bytes", None),
    ("GOOGLE_CHAT_BOOTSTRAP_SPACES", "bootstrap_spaces", None), ("GOOGLE_CHAT_DEBUG_RAW", "debug_raw", None),
)


def _env_enablement() -> Optional[Dict[str, Any]]:
    """``env_enablement_fn``: seed ``PlatformConfig.extra`` from the profile's env before the adapter exists
    (so ``gateway status`` reflects env-only config); ``None`` when the minimum inbound settings are absent."""
    if not _env_inbound_configured():
        return None
    project, subscription, http_events_url = _env_inbound_settings()
    values = [("project_id", project), ("subscription_name", subscription), ("http_events_url", http_events_url),
              ("service_account_json", _get_scoped_secret("GOOGLE_CHAT_SERVICE_ACCOUNT_JSON")
               or _get_scoped_secret("GOOGLE_APPLICATION_CREDENTIALS"))]
    seed = {extra_name: value for extra_name, value in values if value}
    seed.update(_seed_extra_from_env(_ENV_SEED_KEYS, home_env="GOOGLE_CHAT_HOME_CHANNEL"))
    return seed



_SETUP_WALKTHROUGH = """Google Chat needs a GCP project, a Pub/Sub topic + subscription,
and a Service Account with Pub/Sub Subscriber on the subscription.
Walkthrough:
  1. Create or select a GCP project; enable Google Chat API + Cloud Pub/Sub API.
  2. Create a Service Account (no project-level IAM role needed).
  3. Create a Pub/Sub topic (e.g. hermes-chat-events) and a Pull subscription.
  4. On the TOPIC: add chat-api-push@system.gserviceaccount.com as Pub/Sub Publisher.
  5. On the SUBSCRIPTION: grant your Service Account Pub/Sub Subscriber.
  6. Download the Service Account JSON key.
  7. Google Chat API console → Configuration: connection = Cloud Pub/Sub,
     point at the topic, enable 1:1 + group, restrict visibility.
  8. Install the bot in a space (fires ADDED_TO_SPACE and resolves its user_id).

Full guide: website/docs/user-guide/messaging/google_chat.md
"""


def interactive_setup() -> None:
    """``hermes setup`` wizard: print GCP instructions, prompt for env vars, persist to ``~/.hermes/.env``."""
    from hermes_cli.cli_output import print_info, print_success, print_warning, prompt, prompt_yes_no
    from hermes_cli.config import get_env_value, save_env_value
    from hermes_cli.setup_platforms import declines_reconfigure
    if declines_reconfigure("Google Chat", "Reconfigure Google Chat?", "GOOGLE_CHAT_SUBSCRIPTION_NAME"):
        return
    for line in _SETUP_WALKTHROUGH.splitlines():
        print_info(line)
    for question, env_name, required_label, password in (
        ("GCP project ID (e.g. my-project)", "GOOGLE_CHAT_PROJECT_ID", "Project ID", False),
        ("Pub/Sub subscription (projects/<proj>/subscriptions/<sub>)", "GOOGLE_CHAT_SUBSCRIPTION_NAME", "Subscription", False),
        ("Path to Service Account JSON (or inline JSON)", "GOOGLE_CHAT_SERVICE_ACCOUNT_JSON", None, True),
    ):
        value = prompt(question, default=get_env_value(env_name) or "", password=password)
        if not value:
            if required_label is None:
                continue
            print_warning(f"{required_label} is required — skipping Google Chat setup")
            return
        save_env_value(env_name, value.strip())
    if prompt_yes_no("Restrict access to specific users? (recommended)", True):
        allowed = prompt("Allowed user emails (comma-separated)", default=get_env_value("GOOGLE_CHAT_ALLOWED_USERS") or "")
        if allowed:
            save_env_value("GOOGLE_CHAT_ALLOWED_USERS", allowed.replace(" ", ""))
            print_success("Allowlist configured")
        else:
            save_env_value("GOOGLE_CHAT_ALLOWED_USERS", "")
    else:
        save_env_value("GOOGLE_CHAT_ALLOW_ALL_USERS", "true")
        print_warning("⚠️  Open access — anyone who can DM the bot can command it.")
    home = prompt(
        "Home space for cron/notification delivery (e.g. spaces/AAAA, or empty)",
        default=get_env_value("GOOGLE_CHAT_HOME_CHANNEL") or "",
    )
    if home:
        save_env_value("GOOGLE_CHAT_HOME_CHANNEL", home.strip())
    print()
    print_success("Google Chat configuration saved to ~/.hermes/.env")
    print_info("Restart the gateway: hermes gateway restart")


# Strict resource-name patterns: anything outside Chat's documented character set
# is a tampered id trying to break out of the REST URL path.
_GCHAT_CHAT_ID_RE = re.compile(r"^(?:spaces|users)/[A-Za-z0-9_-]+$")
_GCHAT_THREAD_ID_RE = re.compile(r"^spaces/[A-Za-z0-9_-]+/threads/[A-Za-z0-9_-]+$")

# Detail suffixes for ``_standalone_error`` keyed by ``_SACredentialError.kind``.
_STANDALONE_SA_ERRORS = {
    "inline_invalid": "inline SA JSON is invalid: {exc}",
    "not_found": "SA JSON file not found at {path}",
    "file_invalid": "SA JSON file is invalid: {exc}",
    "adc_foreign": ("ADC skipped for this profile: service-account credentials are set in the process environment but "
                    "not in this profile's secret scope"),
    "adc_no_auth": "no SA credentials configured and google-auth is not installed for ADC fallback",
    "adc_failed": "no SA credentials configured and Application Default Credentials are unavailable: {exc}",
}


def _standalone_error(detail: str) -> Dict[str, Any]:
    return send_error(f"Google Chat standalone send: {detail}")


async def _standalone_send(
    pconfig, chat_id: str, message: str, *, thread_id: Optional[str] = None,
    media_files: Optional[List[str]] = None, force_document: bool = False,
) -> Dict[str, Any]:
    """POST one Chat message via REST without the SDK (``send_message_tool`` when the
    gateway runner is not in-process, e.g. ``hermes cron``). Needs SA credentials and a
    validated space name; ``media_files`` / ``force_document`` are signature parity only."""
    if not chat_id:
        return _standalone_error("chat_id (space resource) is required")
    if not _GCHAT_CHAT_ID_RE.match(chat_id):
        return _standalone_error(
            f"chat_id {chat_id!r} must match 'spaces/<id>' or 'users/<id>' with only [A-Za-z0-9_-] in the id")
    if thread_id is not None and not _GCHAT_THREAD_ID_RE.match(thread_id):
        return _standalone_error(f"thread_id {thread_id!r} must match 'spaces/<id>/threads/<id>'")
    extra = getattr(pconfig, "extra", {}) or {}
    sa_value = (
        extra.get("service_account_json") or _get_scoped_secret("GOOGLE_CHAT_SERVICE_ACCOUNT_JSON")
        or _get_scoped_secret("GOOGLE_APPLICATION_CREDENTIALS")
    )
    if service_account is None:
        return _standalone_error("google-auth not installed")
    try:
        from google.auth.transport.requests import Request as _GoogleAuthRequest
    except Exception as e:
        return _standalone_error(f"google-auth import failed: {e}")
    try:
        creds = _load_sa_credentials_from(sa_value)
    except _SACredentialError as err:
        return _standalone_error(_STANDALONE_SA_ERRORS[err.kind].format(exc=err.detail, path=sa_value))
    except Exception as e:
        return _standalone_error(f"credential load failed: {e}")
    # Bound the synchronous token refresh so a hung STS endpoint can't stall cron.
    try:
        await asyncio.wait_for(asyncio.to_thread(creds.refresh, _GoogleAuthRequest()), timeout=10.0)
    except asyncio.TimeoutError:
        return _standalone_error("token refresh timed out")
    except Exception as e:
        return _standalone_error(f"token refresh failed: {e}")
    token = getattr(creds, "token", None)
    if not token:
        return _standalone_error("refreshed credentials have no token")
    try:
        import aiohttp as _aiohttp
    except ImportError:
        return _standalone_error("aiohttp not installed")
    try:
        async with _aiohttp.ClientSession(timeout=_aiohttp.ClientTimeout(total=30.0), trust_env=gateway_trust_env()) as session:
            async with session.post(
                f"https://chat.googleapis.com/v1/{chat_id}/messages", json=_thread_body(message, thread_id),
                headers={"Authorization": f"Bearer {token}", "Content-Type": "application/json"},
            ) as resp:
                if resp.status >= 400:
                    return _standalone_error(f"API returned {resp.status}: {(await resp.text())[:300]}")
                payload = await resp.json()
        return {"success": True, "message_id": payload.get("name")}
    except Exception as e:
        logger.debug("Google Chat standalone send raised", exc_info=True)
        return send_error(f"Google Chat standalone send failed: {e}")


def register(ctx) -> None:
    """Plugin entry point: registers the ``google_chat`` adapter with the platform registry."""
    ctx.register_platform(
        name="google_chat",
        label="Google Chat",
        adapter_factory=lambda cfg: GoogleChatAdapter(cfg),
        check_fn=_check_for_registry,
        ensure_deps_fn=ensure_google_chat_deps,
        validate_config=_validate_config,
        is_connected=_is_connected,
        required_env=["GOOGLE_CHAT_SERVICE_ACCOUNT_JSON"],
        install_hint="Run `hermes setup` to install Google Chat support.",
        setup_fn=interactive_setup,
        env_enablement_fn=_env_enablement,
        cron_deliver_env_var="GOOGLE_CHAT_HOME_CHANNEL",
        standalone_sender_fn=_standalone_send,
        allowed_users_env="GOOGLE_CHAT_ALLOWED_USERS",
        allow_all_env="GOOGLE_CHAT_ALLOW_ALL_USERS",
        # Chat caps text at 4096; margin for typing-marker patches and edit overhead.
        max_message_length=4000,
        emoji="💬",
        allow_update_command=True,
        platform_hint=(
            "You are on Google Chat. Limited markdown subset is rendered: *bold*, _italic_, ~strike~, `code`. "
            "No headings or lists. Message size limit: 4000 characters; longer responses are split across multiple "
            "messages. You are in a space (DM or group). Images render inline; audio, video, and document attachments "
            "render as download cards (no native voice/video UI). To send files, include MEDIA:/absolute/path/to/file "
            "in your response. Native file attachments require the user to run /setup-files once in their own DM — "
            "until they do, file requests fall back to a text notice with the host path. Do NOT generate interactive "
            "Card v2 buttons — Google Chat interactivity is not yet supported by this gateway; ask for typed "
            "confirmations instead. While you are generating a response, a 'Hermes is thinking…' marker message "
            "appears in the space and is deleted once your response is ready. You do NOT have access to Google "
            "Chat-specific APIs — you cannot search space history, list space members, or manage spaces. Do not "
            "promise to perform these actions; explain that you can only read messages sent directly to you and "
            "respond in the same space/thread."
        ),
    )