hermes-chatto-plugin/adapter.py

"""Chatto Platform Adapter for Hermes Agent.

A plugin-based gateway adapter that connects to a Chatto server
(self-hosted team chat) and relays messages to/from the Hermes agent.


The adapter uses the chattolib library for all Chatto API interactions,
including both outbound messaging and realtime WebSocket connections.

"""

from __future__ import annotations

import random

# Put the vendored dependencies for THIS platform on sys.path before importing
# anything from chattolib. Imported relatively as part of the plugin package and
# absolutely when this module is loaded standalone (e.g. by the tests).
try:
    from .vendor_path import setup_vendor_path
except ImportError:  # pragma: no cover - depends on how the module is loaded
    from vendor_path import setup_vendor_path

setup_vendor_path()

import asyncio
import hashlib
import logging
import mimetypes
import os
import re
import tempfile
from datetime import UTC, datetime
from difflib import SequenceMatcher
from enum import StrEnum
from typing import Any, cast
from urllib.parse import unquote, urlsplit

import httpx

logger = logging.getLogger(__name__)

from gateway.config import Platform, PlatformConfig
from gateway.platforms.base import (
    BasePlatformAdapter,
    MessageEvent,
    MessageType,
    ProcessingOutcome,
    SendResult,
    cache_media_bytes,
    get_inbound_media_max_bytes,
    validate_inbound_media_size,
)
from gateway.session import build_session_key

# Chattolib imports (vendored)
# Using vendored chattolib from vendor/chattolib/
# See vendor_chattolib.sh for how to update the vendored copy

# Absolute imports — vendor/ is on sys.path (see above) and chattolib's own
# modules import each other absolutely. Mixing in relative ".vendor.chattolib"
# imports would load a second, distinct copy of every module, so isinstance()
# checks across the two copies would silently fail.
try:
    from chattolib.client import (
        ChattoClient,
    )
    from chattolib.exceptions import (
        ChattoAuthError,
        ChattoError,
    )
    from chattolib.realtime import (
        ChattoRealtimeCloseError,
        ChattoRealtimeError,
        RealtimeEvent,
        stream_events,
    )
    from chattolib.realtime_types import (
        MessageEditedPayload,
        MessagePostedPayload,
        ReactionPayload,
    )
    from chattolib.types import (
        Message,
        MessageAttachment,
        PresenceStatus,
        Room,
        RoomKind,
        RoomWithViewerState,
        User,
    )

except ImportError as e:
    # Fail loudly: continuing here only defers the failure to a confusing
    # NameError somewhere deep in the adapter.
    logger.error("Chatto: failed to import vendored chattolib: %s", e)
    raise


try:
    from .platform_config import (
        ChattoConfiguration,
        ChattoConstants,
    )
except ImportError:  # pragma: no cover - loaded as a top-level module (tests)
    from platform_config import (
        ChattoConfiguration,
        ChattoConstants,
    )


# --------------------------------------------------------------------------- #
# Chat types
# --------------------------------------------------------------------------- #


class HermesChatType(StrEnum):
    """The ``chat_type`` vocabulary the Hermes gateway understands.

    Declared in ``gateway/session.py:161`` as ``"dm", "group", "channel",
    "thread"`` and consumed as a bare string all over the gateway:
    ``SessionSource.description`` (session.py:239) and the PII-redacting
    description in ``build_session_context_prompt`` (session.py:537) both
    branch on these exact values and fall back to a nameless generic case for
    anything else, and ``build_session_key`` puts the value straight into the
    session key.  Passing a chattolib ``RoomKind`` (``"ROOM_KIND_CHANNEL"``)
    therefore does not fail loudly — it just quietly degrades what the agent is
    told about where it is.

    A StrEnum so it stays a drop-in ``str`` at every one of those call sites.

    GROUP vs CHANNEL
    ----------------
    There is no strict contract between the two, and the adapters disagree in
    practice: Slack labels every non-DM conversation ``"group"`` (including real
    channels), Discord uses both, and Telegram reserves ``"channel"`` for actual
    broadcast channels.  The intended reading is ``group`` = ordinary
    multi-participant chat, ``channel`` = broadcast surface.

    The distinction only changes behaviour in three places:

    1. Authorization (``gateway/authz_mixin.py``) — the only security-relevant
       one.  The group-scoped env allowlists apply to ``{"group", "forum"}``
       ONLY, never to ``"channel"``: ``{PLATFORM}_GROUP_ALLOWED_USERS`` /
       ``_GROUP_ALLOWED_CHATS`` (:616), the chat-id allowlist (:708) and the
       Telegram legacy shim (:724).  The adapter-delegation paths in turn treat
       all three alike (:461, :649, :674, :694), where the value only picks
       ``group_allow_from`` over ``allow_from`` from ``config.extra``.
       For Chatto both choices are equivalent today: those group env maps hold
       Telegram and QQBot only (:535-541), and our own allowlist runs through
       ``CHATTO_ALLOWED_USERS``, which is chat_type-independent.
    2. What the agent is told — ``SessionSource.description`` renders
       ``"group: Name"`` vs ``"channel: Name"`` (session.py:239-246), likewise
       the PII-redacted variant (session.py:537-544).
    3. The session key, which embeds the literal (session.py:1192).  Changing
       the value for a room re-buckets its existing sessions.

    Explicitly NOT affected: ``is_shared_multi_user_session`` (session.py:1063)
    only looks at ``"dm"`` and ``thread_id``, so sender prefixes, the multi-user
    prompt line and ``group_sessions_per_user`` treat group and channel
    identically.
    """

    DM = "dm"
    GROUP = "group"
    CHANNEL = "channel"
    # Emitted by adapters whose thread events are their own chat type (Slack,
    # Discord). We don't: a Chatto thread keeps its room's chat_type and is
    # identified by ``thread_id`` on the source instead. Listed for the record,
    # because build_session_key rewrites the slot to "thread" itself
    # (session.py:1190).
    THREAD = "thread"
    # Not declared in session.py:161 but real: Telegram forum topics travel as
    # "forum", and the authz group allowlists above accept it alongside "group".
    # Chatto has no equivalent, so we never emit it.


# Chatto only distinguishes DMs from channels. UNSPECIFIED means the server
# sent a kind this vendored chattolib doesn't know: map it to the generic
# multi-user bucket rather than guessing "channel", and never to "dm" — that
# value drives session isolation (is_shared_multi_user_session, session.py:1063)
# and would silently turn a room into a private conversation.
#
# CHANNEL for RoomKind.CHANNEL is the descriptive choice and carries no
# behavioural cost (see the GROUP vs CHANNEL note above). Switching to GROUP for
# Slack parity would be this one line — plus the re-bucketing of existing
# sessions that point 3 of that note describes.
_ROOM_KIND_TO_CHAT_TYPE: dict[RoomKind, HermesChatType] = {
    RoomKind.DM: HermesChatType.DM,
    RoomKind.CHANNEL: HermesChatType.CHANNEL,
    RoomKind.UNSPECIFIED: HermesChatType.GROUP,
}


def chat_type_for_room_kind(kind: RoomKind | None) -> HermesChatType:
    """Map a chattolib RoomKind onto the gateway's chat_type vocabulary.

    An unknown or missing kind becomes ``GROUP`` — see ``_ROOM_KIND_TO_CHAT_TYPE``.
    """
    if kind is None:
        return HermesChatType.GROUP
    return _ROOM_KIND_TO_CHAT_TYPE.get(kind, HermesChatType.GROUP)


class ChannelPolicy(StrEnum):
    """How a channel-kind room treats an inbound message.

    Derived per room from ``CHATTO_REQUIRE_MENTION_ROOMS`` /
    ``CHATTO_OPTIONAL_MENTION_ROOMS`` — see ``_room_policy``. A StrEnum
    so the values log readably without a formatting dance.
    """

    # Listed for unaddressed answers: every message is dispatched, and one
    # aimed at a named colleague gets a 🫥 acknowledgement instead of a reply.
    OPEN = "open"
    # Listed for addressed-only participation: dispatches only messages that
    # mention the bot (@name or a broadcast handle); others are dropped.
    REQUIRE_MENTION = "require_mention"
    # Listed in neither config: the room is silent — not dispatched at all,
    # read-only like any unlisted membership.
    SILENT = "silent"


# Blocking filesystem/network helpers. The adapter runs on the shared gateway
# event loop, so file reads and HTTP downloads are pushed to a worker thread
# via asyncio.to_thread — a slow disk or dead image URL must not stall every
# platform's message processing.


def _read_file_bytes(path: str) -> bytes:
    """Read a whole file synchronously (run via asyncio.to_thread)."""
    with open(path, "rb") as f:
        return f.read()


def _write_file_bytes(path: str, data: bytes) -> None:
    """Write bytes to a file synchronously (run via asyncio.to_thread)."""
    with open(path, "wb") as f:
        f.write(data)


# --------------------------------------------------------------------------- #
# Adapter
# --------------------------------------------------------------------------- #


def hermes_adapter_factory(config: PlatformConfig):
    """Construct a ChattoAdapter from a PlatformConfig."""
    return ChattoAdapter(config)


class ChattoAdapter(BasePlatformAdapter):
    """Chatto platform adapter.

    Receives messages via WebSocket realtime, sends via ConnectRPC.
    """

    _SPLIT_THRESHOLD = 9900
    # Read by BasePlatformAdapter.max_message_length_for_chat(), which the
    # gateway and the stream consumer use to chunk outgoing messages. Without
    # it they fall back to 4096 and split Chatto messages far earlier than
    # necessary — send() itself already truncates at 10000.
    MAX_MESSAGE_LENGTH = ChattoConstants.MAX_MESSAGE_LENGTH
    splits_long_messages = True
    supports_code_blocks: bool = True
    supports_status_text: bool = True  # client.update_custom_status

    def __init__(self, pconfig: PlatformConfig):
        """Signature needs to be compatible with BasePlatformAdapter.__init__."""
        super().__init__(
            config=pconfig, platform=Platform(ChattoConstants.PLATFORM_NAME)
        )
        # "extra" has been pre-populated by Hermes from config.yaml's extra block.

        # --- Configuration from our configuration data class with some logic ---
        self.chatto_config: ChattoConfiguration = ChattoConfiguration(pconfig)

        # ------ State -------
        # Our own user, filled in by connect(). Events arriving before connect()
        # completes must not blow up on an undefined attribute.
        self.me: User | None = None

        # --- Runtime state ---
        self._room_names: dict[str, str] = {}
        self._room_kinds: dict[str, RoomKind] = {}
        # Event IDs already processed — chattolib may redeliver events across
        # reconnects, so every inbound event is checked against this list.
        self._seen: list[str] = []
        # Message IDs this adapter has handed to the gateway (posted or
        # edit-re-dispatched). Edits of anything on this list never start a
        # fresh turn — that is the lock against re-answering settled
        # conversations by editing old messages.
        self._dispatched_ids: list[str] = []
        # session_key -> message ID currently being processed there. Written
        # by on_processing_start, cleared by on_processing_complete; an edit
        # landing on the recorded ID is a mid-run correction.
        self._processing: dict[str, str] = {}
        self._joined_room_ids: list[str] = []
        # Rooms the server force-joined everyone into (Room.universal) — used
        # only for [universal] tags in the joined-rooms log line, never for
        # gating.
        self._universal_room_ids: set[str] = set()
        # One-shot guard for the unjoined-home-channel warning in _refresh_rooms.
        self._home_warning_logged = False
        self._ws_task: asyncio.Task | None = None
        self._presence_task: asyncio.Task | None = None

        # Persistent typing indicator loops per room
        self._typing_tasks: dict[str, asyncio.Task] = {}

        # Member directory cache: user_id -> user info dict
        self._user_cache: dict[str, User] = {}
        # Handle -> does a user hold it. Cached both ways; see _mentions_someone_else.
        self._known_handles: dict[str, bool] = {}

        # Chattolib client cache and lock for async access.
        self._chatto_client: ChattoClient | None = None
        self._chatto_client_lock: asyncio.Lock = asyncio.Lock()

    # ------------------------------------------------------------------ #
    # Auth
    # ------------------------------------------------------------------ #

    async def _get_chatto_client(self: ChattoAdapter) -> ChattoClient | None:
        """Return the shared ChattoClient, creating and logging in on first use.

        The default way to get a client. The fast path is a plain attribute
        read; first creation runs under a lock so concurrent callers log in
        exactly once. Returns ``None`` when no client exists yet or creation
        failed (bad credentials, unreachable server) — a normal state during
        startup, shutdown and reconnects, not an exceptional one. Callers
        decide what "no client" means for them, as a guard clause:

            client = await self._get_chatto_client()
            if client is None:
                logger.warning("Chatto: dropping X - no client available")
                return
        """
        if self._chatto_client is not None:
            return self._chatto_client

        async with self._chatto_client_lock:
            if self._chatto_client is not None:
                return self._chatto_client

            try:
                client = await self._open_client(
                    base_url=self.chatto_config.base_url.value,
                    login=self.chatto_config.login.value,
                    password=self.chatto_config.password.value,
                    token=self.chatto_config.token.value,
                )
                self._chatto_client = client
                logger.info(
                    "Chatto: logged in as '%s' via chattolib",
                    self.chatto_config.login.value,
                )
                return client
            except ChattoAuthError as e:
                logger.error("Chatto: authentication failed: %s", e)
                return None
            except (ChattoError, ValueError) as e:
                logger.error("Chatto: failed to create client: %s", e)
                return None

    async def _require_chatto_client(self) -> ChattoClient:
        """Return a ChattoClient or raise RuntimeError if unavailable.

        The exception-flavoured variant of :meth:`_get_chatto_client`, for
        callers whose surrounding machinery already routes exceptions.
        Currently that is only the realtime event loop, whose except chain
        turns the raise into a logged warning plus a backed-off reconnect —
        no special "no client" branch needed there. Everywhere else, prefer
        the ``is None`` guard shown in :meth:`_get_chatto_client`.
        """
        client = await self._get_chatto_client()
        if client is None:
            raise RuntimeError("Chatto client unavailable")
        return client

    async def _ensure_token(self) -> bool:
        """Ensure we have a logged-in Chatto client and token."""
        if self.chatto_config.token.value and isinstance(
            self._chatto_client, ChattoClient
        ):
            return True

        client = await self._get_chatto_client()
        return client is not None

    # ------------------------------------------------------------------ #
    # Connection
    # ------------------------------------------------------------------ #
    async def _open_client(
        self,
        *,
        base_url: str,
        login: str,
        password: str,
        token: str | None = None,
    ) -> ChattoClient:
        """Return a connected ``ChattoClient`` using token or login/password.

        Token wins when both are configured. Raises ValueError when neither a
        token nor login+password is set — caught upstream as a normal
        creation failure, so misconfiguration reads as a logged error instead
        of a crash.
        """
        if token:
            return ChattoClient(token=token, base_url=base_url)
        if not login or not password:
            raise ValueError("Chatto: neither token nor login/password configured")
        return await ChattoClient.login(login, password, base_url=base_url)

    async def connect(self, *, is_reconnect: bool = False) -> bool:
        """Connect to Chatto and start the realtime event stream.

        BasePlatformAdapter override
        """
        logger.info("Chatto: connecting...")

        if not await self._ensure_token():
            return False

        client = await self._get_chatto_client()
        if client is None:
            self._set_fatal_error(
                "connect_failed", "Chatto client not available", retryable=True
            )
            return False

        # Get our first own user info
        try:
            self.me = await client.me()
        except Exception as exc:
            logger.error("Chatto: failed to get user info: %s", exc)
            self._set_fatal_error(
                "chatto_auth_failed",
                f"Chatto auth failed: {exc}",
                retryable=False,
            )
            try:
                if self._chatto_client is not None:
                    await self._chatto_client.close()
            finally:
                self._chatto_client = None
            return False

        # Announce online presence so the bot appears online in the member list.
        # The server treats this as a TTL, so _presence_refresh_loop below has to
        # keep re-announcing it — a single call here lapses back to offline.
        await self._announce_online()

        self._closing = False
        # Start background realtime WS event stream loop.
        self._ws_task = asyncio.create_task(
            self._chattolib_event_loop(),
            name="chatto-event-stream",
        )
        self._presence_task = asyncio.create_task(
            self._presence_refresh_loop(),
            name="chatto-presence-refresh",
        )
        self._mark_connected()

        logger.info(
            "Chatto: connected and authentiated to %s using login:'%s' (display_name:'%s' id: '%s')",
            self.chatto_config.base_url.value,
            self.me.login,
            self.me.display_name,
            self.me.id,
        )

        return True

    async def _announce_online(self) -> bool:
        """Tell the server we are online. Returns whether the call got through.

        Logged at warning level on failure: a silently dropped presence call is
        indistinguishable from a bot that is simply not running.
        """
        client = await self._get_chatto_client()
        if client is None:
            logger.warning(
                "Chatto: presence refresh failed, bot may appear offline: no client"
            )
            return False
        try:
            await client.update_presence(status=PresenceStatus.ONLINE)
            return True
        except Exception as exc:
            logger.warning(
                "Chatto: presence refresh failed, bot may appear offline: %s", exc
            )
            return False

    async def _presence_refresh_loop(self) -> None:
        """Re-announce ONLINE until disconnect, since presence expires server-side.

        Failures are not fatal — the next tick tries again, so a blip in the
        presence endpoint costs at most one interval of visible offline time.
        """
        while not self._closing:
            await self._sleep_interruptible(ChattoConstants.PRESENCE_REFRESH_INTERVAL)
            if self._closing:
                return
            await self._announce_online()

    async def disconnect(self) -> None:
        """Stop WebSocket, presence refresh, typing tasks, and clear state.

        BasePlatformAdapter override
        """
        # No explicit offline broadcast: chattolib rejects OFFLINE outright
        # ("stop refreshing to go offline"), so cancelling the refresh loop
        # below is what actually takes the bot offline.
        self._closing = True

        # Cancel all typing tasks
        for chat_id in list(self._typing_tasks.keys()):
            await self.stop_typing(chat_id)

        if self._ws_task and not self._ws_task.done():
            self._ws_task.cancel()
            try:
                await self._ws_task
            except (asyncio.CancelledError, Exception):
                logger.debug(
                    "Chatto: websocket task ended during disconnect", exc_info=True
                )
            self._ws_task = None

        if self._presence_task and not self._presence_task.done():
            self._presence_task.cancel()
            try:
                await self._presence_task
            except (asyncio.CancelledError, Exception):
                logger.debug(
                    "Chatto: presence task ended during disconnect", exc_info=True
                )
        self._presence_task = None

        if self._chatto_client:
            try:
                await self._chatto_client.close()
            except Exception:
                logger.exception("Chatto: error closing client")
            finally:
                self._chatto_client = None

        logger.info("Chatto: disconnected")
        self._mark_disconnected()

    async def _seed_room(self, room_id: str) -> None:
        """Seed high-water mark from the newest events so a restart doesn't replay history."""
        try:
            client = await self._get_chatto_client()
            if client is None:
                logger.debug(
                    "Chatto: _seed_room aborted - no client available for %s", room_id
                )
                return
            timeline_page = await client.get_room_events(room_id)

            for ev in timeline_page.events:
                if ev.id:
                    self._mark_seen(ev.id)
            logger.debug(
                "Chatto: seeded room %s with %d events",
                room_id,
                len(timeline_page.events),
            )
        except Exception as e:
            logger.warning("Chatto: get room events failed for %s: %s", room_id, e)

    # ------------------------------------------------------------------ #
    # Realtime Event List
    # ------------------------------------------------------------------ #

    def _mark_seen(self, event_id: str) -> None:
        self._seen.append(event_id)
        while len(self._seen) > ChattoConstants.SEEN_CAP:
            self._seen.remove(self._seen[0])  # fastest removal of first item in a list.

    def _is_seen(self, event_id: str) -> bool:
        return event_id in self._seen

    # ------------------------------------------------------------------ #
    # WebSocket Realtime Transport
    # ------------------------------------------------------------------ #

    def _own_handles(self) -> set[str]:
        """The handles that address this bot, lowercased for comparison.

        Chatto resolves mentions case-insensitively (FDR-006), so ``@Hermes_Bot``
        and ``@hermes_bot`` are the same handle everywhere in our gates.
        """
        if not self.me:
            return set()
        return {
            handle.lower() for handle in (self.me.login, self.me.display_name) if handle
        }

    def _mention_candidates(self, body: str) -> list[str]:
        """Candidate @-handles in a message body, in order of appearance.

        Mirrors the Chatto web frontend's extraction (apps/frontend/src/lib/
        mentions.ts upstream): candidates come from ``ChattoConstants.
        MENTION_RE`` outside code regions. Mentions inside fenced code blocks
        and inline code spans do not resolve upstream either, so a ``@bob``
        quoted in a snippet must not gate our behaviour.
        """
        without_fences = re.sub(r"(?s)(```|~~~).*?(\1|$)", " ", body)
        without_code = re.sub(r"`[^`\n]*`", " ", without_fences)
        return ChattoConstants.MENTION_RE.findall(without_code)

    def _mentions_me(self, body: str) -> bool:
        """Whether the message addresses this bot.

        By login, by display name, or by a broadcast handle — ``@here`` speaks
        to everyone present and the bot is one of them, so naming a colleague
        alongside it does not take the bot out of the audience. Matching is
        case-insensitive, like every mention resolution in Chatto.
        """
        own = self._own_handles()
        for handle in self._mention_candidates(body):
            lowered = handle.lower()
            if lowered in own or lowered in ChattoConstants.BROADCAST_MENTIONS:
                return True
        return False

    async def _handle_belongs_to_a_user(self, handle: str) -> bool:
        """Whether ``handle`` is the login of a real Chatto user.

        The API carries no mention entities — ``mention_confirmation_token`` is
        reserved in the message descriptor — so an @-token is only a candidate
        until the directory confirms it. Results are cached both ways under the
        lowercased handle (the mention namespace is case-insensitive per
        FDR-006), since the same handles recur and a miss is as reusable as a
        hit. Only logins are looked up: matching another user's display name,
        as the web frontend does against its room member list, has no directory
        equivalent here.
        """
        cache_key = handle.lower()
        known = self._known_handles.get(cache_key)
        if known is not None:
            return known
        client = await self._get_chatto_client()
        if client is None:
            # Unresolved means "not confirmed", so the message goes through.
            return False
        try:
            member = await client.get_user(login=handle)
        except Exception as exc:
            logger.debug("Chatto: could not resolve handle @%s: %s", handle, exc)
            return False
        exists = member is not None and member.user is not None
        self._known_handles[cache_key] = exists
        return exists

    async def _mentions_someone_else(self, body: str) -> bool:
        """Whether the message @-mentions a person who is not this bot.

        Broadcast handles are not a person — they address everyone present,
        the bot included, so they do not count as someone else. A handle no
        user holds is not a mention at all: someone writing *about* mentioning
        ("per @-mention", "@nonexistent") is talking to us, and staying silent
        on a false positive is worse than answering one.
        """
        own = self._own_handles()
        for handle in self._mention_candidates(body):
            lowered = handle.lower()
            if lowered in ChattoConstants.BROADCAST_MENTIONS:
                continue
            if lowered in own:
                continue
            if await self._handle_belongs_to_a_user(handle):
                return True
        return False

    def _check_auth(self, user: User) -> bool:
        """Whether this Chatto user may talk to the agent.

        Deliberately our own gate instead of the gateway's authz_mixin: its
        group allowlists key on chat_type and per-platform env vars
        (``{PLATFORM}_GROUP_ALLOWED_USERS``), none of which fit Chatto's one
        flat member directory. ``CHATTO_ALLOWED_USERS`` matches login and id,
        ``CHATTO_ALLOW_ALL_USERS`` overrides both — the gate stays
        chat_type-independent by design.
        """
        if self.chatto_config.allow_all_users.value:
            return True
        if user.login in self.chatto_config.allowed_users.value:
            return True
        if user.id in self.chatto_config.allowed_users.value:
            return True
        logger.warning(
            "Chatto: rejecting message from unauthorized user '%s' (%s)",
            user.login,
            user.id,
        )
        return False

    # ------------------------------------------------------------------ #
    # Room management over DM (/join, /leave)
    # ------------------------------------------------------------------ #

    _DM_COMMANDS = ("/join", "/leave")

    async def _handle_dm_command(self, room_id: str, body: str) -> bool:
        """Run a ``/join`` or ``/leave`` admin command sent as a direct message.

        Returns True when ``body`` is one of the commands — whether it
        succeeded or not — so the caller keeps it out of the agent pipeline.
        Membership lives on the Chatto server: a joined room reappears in
        every future ``list_rooms()`` and therefore survives restarts.
        """
        verb, _, argument = body.strip().partition(" ")
        if verb.lower() not in self._DM_COMMANDS:
            return False

        client = await self._get_chatto_client()
        if client is None:
            await self.send(chat_id=room_id, content="Chatto client is not connected.")
            return True

        argument = argument.strip()
        if not argument:
            await self.send(
                chat_id=room_id,
                content="Usage: /join <room-id or #name> | /leave <room-id or #name>",
            )
            return True

        error, target = await self._resolve_room_target(client, argument)
        if error or target is None:
            await self.send(chat_id=room_id, content=error or "Room lookup failed.")
            return True

        if verb.lower() == "/join":
            reply = await self._run_join(client, target)
        else:
            reply = await self._run_leave(client, target)
        await self.send(chat_id=room_id, content=reply)
        return True

    async def _resolve_room_target(
        self,
        client: ChattoClient,
        argument: str,
    ) -> tuple[str | None, RoomWithViewerState | None]:
        """Resolve a /join//leave argument to a room.

        ``#name`` is looked up case-insensitively in a fresh directory scan
        (which also refreshes our name/kind caches); anything else is treated
        as a room ID and verified via GetRoom. An ambiguous name comes back as
        an error naming the candidates, so the admin can retry with an ID.
        """
        if not argument.startswith("#"):
            state = await client.get_room(argument)
            if state is None or state.room is None:
                return f"No room with ID '{argument}'.", None
            return None, state

        wanted = argument[1:].strip().casefold()
        # (state, room) pairs: a listed match's room is already narrowed here,
        # so the candidate listing below needs no fresh Optional dance.
        matches: list[tuple[RoomWithViewerState, Room]] = []
        for state in await client.list_rooms() or []:
            room_obj = state.room if state else None
            if room_obj and (room_obj.name or "").strip().casefold() == wanted:
                matches.append((state, room_obj))
                self._room_names[room_obj.id] = room_obj.name
                self._room_kinds[room_obj.id] = room_obj.kind
        if not matches:
            return f"No room named '{argument}'.", None
        if len(matches) > 1:
            candidates = "\n".join(f"• {room.name} ({room.id})" for _, room in matches)
            return (
                f"Several rooms are named '{argument}' — pick one by ID:\n{candidates}"
            ), None
        return None, matches[0][0]

    async def _run_join(self, client: ChattoClient, state: RoomWithViewerState) -> str:
        """Join a room via RoomService/JoinRoom and track it as joined.

        An account that already holds membership (invited natively in Chatto)
        needs no JoinRoom call — it only gets seeded and added to the list.
        Channel-kind rooms additionally report their mention-list status,
        because a channel on neither list stays silent and this reply is
        where users copy the room ID from (see ``_channel_join_hint``).
        """
        room_obj = state.room
        if room_obj is None:
            # Unreachable via _resolve_room_target: both of its paths only
            # return states whose room they already inspected.
            return "Chatto returned an empty room record — try again."
        label = f"'{room_obj.name}' ({room_obj.id})"
        joined_room = room_obj
        if not state.viewer_state.is_member:
            try:
                joined_room = await client.join_room(room_obj.id) or room_obj
            except ChattoError as exc:
                logger.warning("Chatto: /join failed for %s (%s)", room_obj.id, exc)
                return f"Could not join {label}: {exc}"
        self._room_names[joined_room.id] = joined_room.name
        self._room_kinds[joined_room.id] = joined_room.kind
        if joined_room.id not in self._joined_room_ids:
            # Same rule as _refresh_rooms: silent rooms are joined read-only
            # — seeding history nothing will ever answer would be waste.
            if self._is_respond_room(joined_room.id):
                await self._seed_room(joined_room.id)
            else:
                logger.info(
                    "Chatto: %s is on neither mention list - joined read-only",
                    label,
                )
            self._joined_room_ids.append(joined_room.id)
        if room_obj.kind != RoomKind.DM:
            head = (
                f"Already a member of {label}."
                if state.viewer_state.is_member
                else f"Joined {label}."
            )
            return f"{head}\n{self._channel_join_hint(room_obj.id)}"
        if state.viewer_state.is_member:
            return f"Already a member of {label} — listening there."
        return f"Joined {label}."

    async def _run_leave(self, client: ChattoClient, state: RoomWithViewerState) -> str:
        """Leave a room via RoomService/LeaveRoom and drop it from the joined list.

        Two rooms are refused: a DM conversation cannot be left, and leaving
        the configured home channel would silently break cron/notification
        delivery, which posts there through the standalone sender.
        """
        room_obj = state.room
        if room_obj is None:
            # Same invariant as _run_join: _resolve_room_target pre-inspects.
            return "Chatto returned an empty room record — try again."
        label = f"'{room_obj.name}' ({room_obj.id})"
        if room_obj.kind == RoomKind.DM:
            return "Direct messages cannot be left."
        home_id = (self.chatto_config.home_channel.value or "").strip()
        if home_id == room_obj.id:
            return (
                f"{label} is the configured home channel "
                "(CHATTO_HOME_CHANNEL); leaving it would break cron and "
                "notification delivery. Point CHATTO_HOME_CHANNEL elsewhere first."
            )
        try:
            left = await client.leave_room(room_obj.id)
        except ChattoError as exc:
            logger.warning("Chatto: /leave failed for %s (%s)", room_obj.id, exc)
            return f"Could not leave {label}: {exc}"
        if not left:
            return f"Chatto refused to leave {label}."
        if room_obj.id in self._joined_room_ids:
            self._joined_room_ids.remove(room_obj.id)
        return f"Left {label}."

    def _channel_join_hint(self, room_id: str) -> str:
        """The mention-list status appended to a channel-kind /join reply.

        Users do not know their room IDs by heart — this reply is where they
        copy them from, so a silent channel names both env vars verbatim,
        ready to paste into ~/.hermes/.env. Configuration resolves once at
        gateway startup, hence the restart note.
        """
        policy = self._room_policy(room_id)
        if policy == ChannelPolicy.REQUIRE_MENTION:
            return (
                "This channel answers only @mentions "
                "(listed in CHATTO_REQUIRE_MENTION_ROOMS)."
            )
        if policy == ChannelPolicy.OPEN:
            return (
                "This channel answers every message "
                "(listed in CHATTO_OPTIONAL_MENTION_ROOMS)."
            )
        return (
            "This channel stays silent until you list its ID in"
            " ~/.hermes/.env (then restart the gateway):\n"
            f"  CHATTO_REQUIRE_MENTION_ROOMS={room_id}   <- answer only @mentions\n"
            f"  CHATTO_OPTIONAL_MENTION_ROOMS={room_id}  <- answer every message"
        )

    # ------------------------------------------------------------------ #
    # Inbound attachments
    # ------------------------------------------------------------------ #

    async def _download_attachment_bytes(self, url: str) -> bytes:
        """Download an attachment, refusing to buffer more than the gateway cap.

        The Content-Length header is checked first so an oversized asset is
        rejected before a single chunk is read; the running total is re-checked
        as chunks arrive, because a missing or lying header must not smuggle an
        unbounded body past the cap.
        """
        max_bytes = get_inbound_media_max_bytes()
        chunks: list[bytes] = []
        total = 0
        async with (
            httpx.AsyncClient(
                timeout=ChattoConstants.HTTP_TIMEOUT,
                follow_redirects=True,
            ) as http,
            http.stream("GET", url) as resp,
        ):
            resp.raise_for_status()
            declared = resp.headers.get("content-length")
            if declared:
                try:
                    declared_size = int(declared)
                except ValueError:
                    logger.debug("Chatto: ignoring invalid Content-Length %r", declared)
                else:
                    validate_inbound_media_size(
                        declared_size,
                        media_type="attachment",
                        max_bytes=max_bytes,
                    )
            async for chunk in resp.aiter_bytes():
                total += len(chunk)
                validate_inbound_media_size(
                    total,
                    media_type="attachment",
                    max_bytes=max_bytes,
                )
                chunks.append(chunk)
        return b"".join(chunks)

    async def _cache_attachments(
        self,
        attachments: list[MessageAttachment],
    ) -> tuple[list[str], list[str], list[str]]:
        """Download message attachments into the gateway media cache.

        Returns ``(media_urls, media_types, media_kinds)`` — the paths are
        agent-visible cache paths, exactly what ``cache_media_bytes`` yields for
        every other platform.  A failing attachment is logged and skipped: the
        message itself still reaches the agent.
        """
        media_urls: list[str] = []
        media_types: list[str] = []
        media_kinds: list[str] = []

        for att in attachments:
            url = att.asset_url.url if att.asset_url else ""
            filename = att.filename
            content_type = att.content_type
            if not url:
                # Videos are announced before transcoding finishes, so the
                # signed URL can legitimately be missing on arrival.
                logger.debug(
                    "Chatto: attachment '%s' has no asset URL yet, skipping",
                    filename,
                )
                continue
            try:
                data = await self._download_attachment_bytes(url)
                cached = cache_media_bytes(
                    data,
                    filename=filename,
                    mime_type=content_type,
                )
            except Exception as e:
                logger.warning(
                    "Chatto: failed to cache attachment '%s' (%s): %s",
                    filename,
                    content_type,
                    e,
                )
                continue
            if cached is None:
                logger.warning(
                    "Chatto: attachment '%s' (%s) could not be cached, skipping",
                    filename,
                    content_type,
                )
                continue
            media_urls.append(cached.path)
            media_types.append(cached.media_type)
            media_kinds.append(cached.kind)

        return media_urls, media_types, media_kinds

    @staticmethod
    def _message_type_for_media_kinds(media_kinds: list[str]) -> MessageType:
        """Pick the MessageType for a set of cached attachment kinds."""
        if "document" in media_kinds:
            return MessageType.DOCUMENT
        if "image" in media_kinds:
            return MessageType.PHOTO
        if "video" in media_kinds:
            return MessageType.VIDEO
        if "audio" in media_kinds:
            return MessageType.AUDIO
        return MessageType.TEXT

    def _room_policy(self, room_id: str) -> ChannelPolicy:
        """Which of the mention lists a channel-kind room is on.

        The two lists are mutually exclusive (enforced by
        ``hermes_validate_config``), so membership decides: optional beats
        require in the face of contradictory runtime config, and a room on
        neither list stays silent.
        """
        if room_id in self.chatto_config.optional_mention_rooms.value:
            return ChannelPolicy.OPEN
        if room_id in self.chatto_config.require_mention_rooms.value:
            return ChannelPolicy.REQUIRE_MENTION
        return ChannelPolicy.SILENT

    def _is_respond_room(self, room_id: str) -> bool:
        """Whether inbound messages from this room reach the agent pipeline.

        Chatto knows only DMs and channels, so the split is ``kind == DM``:
        a DM is always a respond room (``/join`` must stay reachable), every
        other room — channel-kind or an unknown kind, which is how servers
        that never set ``kind`` show up — opts in through the mention lists.
        A room whose policy is SILENT stays read-only (marked as read, never
        seeded or answered).
        """
        if self._room_kinds.get(room_id) == RoomKind.DM:
            return True
        return self._room_policy(room_id) != ChannelPolicy.SILENT

    async def _dispatch_message_posted(self, payload: MessagePostedPayload) -> None:
        # Respond-room gate first: read-only memberships must not cost a
        # single API call, so this runs before fetch_message and _get_chatto_client.
        if not self._is_respond_room(payload.room_id):
            logger.debug(
                "Chatto: message from read-only room %s ignored", payload.room_id
            )
            return

        client = await self._get_chatto_client()
        if client is None:
            logger.warning("Chatto: dropping message - no client available")
            return
        logger.debug("Chatto WS: 'message_posted' payload:%s", payload)

        message = await payload.fetch_message(client=client)
        if message is None or message.deleted_at:
            return
        message_body = message.body or ""
        logger.debug("message: %s", message)

        # A message carrying only an image/PDF has an empty body — dropping it
        # here is what made attachments sent to Hermes disappear silently.
        if not message_body and not message.attachments:
            return

        event = await self._admit_and_build(
            client,
            room_id=payload.room_id,
            message=message,
            source_message_id=payload.message_event_id,
            thread_root_event_id=payload.thread_root_event_id or None,
        )
        if event is None:
            return

        self._remember_dispatched(event.message_id or "")
        logger.info("Chatto: dispatching message to Hermes")
        await self.handle_message(event)
        return

    def _remember_dispatched(self, message_id: str) -> None:
        """Record a message ID as handed to the gateway, capped like _seen."""
        if not message_id:
            return
        self._dispatched_ids.append(message_id)
        while len(self._dispatched_ids) > ChattoConstants.SEEN_CAP:
            self._dispatched_ids.remove(self._dispatched_ids[0])

    def _edit_is_fresh(self, message: Message) -> bool:
        """Whether this edit is young enough to still be processed.

        Age is measured against the posting time, so an edit to an hours-old
        message cannot resurrect a settled conversation even when it arrives
        right now.
        """
        if message.created_at is None or message.updated_at is None:
            return True
        age_seconds = (message.updated_at - message.created_at).total_seconds()
        return age_seconds <= self.chatto_config.edit_window.value

    def _session_key_for(self, source) -> str:
        """The gateway's own session key for this source.

        Built with exactly the inputs ``handle_message`` uses, so lookups in
        ``_processing`` and calls to ``cancel_session_processing`` hit the
        same session the gateway is running.
        """
        return build_session_key(
            source,
            group_sessions_per_user=self.config.extra.get(
                "group_sessions_per_user", True
            ),
            thread_sessions_per_user=self.config.extra.get(
                "thread_sessions_per_user", False
            ),
        )

    async def _dispatch_message_edited(self, payload: MessageEditedPayload) -> None:
        """Route an inbound edit according to the edit-dispatch contract.

        Three outcomes for the edited message:

        - currently being processed → cancel that turn and re-dispatch with
          the corrected text (the cancelled turn reports 🚫 via its
          CANCELLED outcome hook),
        - never dispatched (e.g. a forgotten @mention added later) → re-run
          the admission gates against the new body and answer for real,
        - already answered → stay answered.

        Edits whose text parses as a DM membership command are dropped: the
        command ran when the message was posted and must not run again.
        """
        if not self.chatto_config.edit_dispatch.value:
            return
        # Read-only memberships cost no API call, mirroring the posted path.
        if not self._is_respond_room(payload.room_id):
            logger.debug("Chatto: edit from read-only room %s ignored", payload.room_id)
            return

        client = await self._get_chatto_client()
        if client is None:
            logger.warning("Chatto: dropping edit - no client available")
            return
        logger.debug("Chatto WS: 'message_edited' payload:%s", payload)

        message = await payload.fetch_message(client=client)
        if message is None or message.deleted_at:
            return
        message_body = message.body or ""
        if not message_body and not message.attachments:
            return
        if not self._edit_is_fresh(message):
            logger.debug(
                "Chatto: edit of msg %s outside the edit window",
                payload.message_event_id,
            )
            return

        # Cheap triage before the admission pipeline: an edit to an
        # already-settled message (dispatched, neither running nor queued)
        # must not cost get_room/media calls or re-fire acknowledgements.
        was_dispatched = payload.message_event_id in self._dispatched_ids
        if (
            was_dispatched
            and payload.message_event_id not in self._processing.values()
            and not any(
                pending.message_id == payload.message_event_id
                for pending in self._pending_messages.values()
            )
        ):
            logger.debug(
                "Chatto: edit of already-answered msg %s ignored",
                payload.message_event_id,
            )
            return

        event = await self._admit_and_build(
            client,
            room_id=payload.room_id,
            message=message,
            source_message_id=payload.message_event_id,
            thread_root_event_id=message.thread_root_event_id or None,
            allow_dm_commands=False,
        )
        if event is None:
            return

        session_key = self._session_key_for(event.source)
        if self._processing.get(session_key) == payload.message_event_id:
            logger.info(
                "Chatto: msg %s edited mid-run - restarting the turn",
                payload.message_event_id,
            )
            # The cancelled task's completion hook clears _processing and
            # reports 🚫 before this coroutine moves on, because cancel
            # awaits the task. Queued follow-ups must survive.
            await self.cancel_session_processing(
                session_key, release_guard=True, discard_pending=False
            )
        elif payload.message_event_id not in self._dispatched_ids:
            logger.info(
                "Chatto: msg %s was never dispatched - edit starts a fresh turn",
                payload.message_event_id,
            )
        else:
            pending = self._pending_messages.get(session_key)
            if pending is not None and pending.message_id == payload.message_event_id:
                # Still queued behind the running turn: correct it in place
                # instead of answering stale wording later.
                pending.text = event.text
                logger.info(
                    "Chatto: queued msg %s updated to its edited text",
                    payload.message_event_id,
                )
                return
            logger.debug(
                "Chatto: edit of already-answered msg %s ignored",
                payload.message_event_id,
            )
            return

        self._remember_dispatched(event.message_id or "")
        logger.info("Chatto: dispatching edited message to Hermes")
        await self.handle_message(event)

    async def _admit_and_build(
        self,
        client: ChattoClient,
        *,
        room_id: str,
        message: Message,
        source_message_id: str,
        thread_root_event_id: str | None,
        allow_dm_commands: bool = True,
    ) -> MessageEvent | None:
        """Run one hydrated inbound message through the admission pipeline.

        Shared by the posted and the edited path: user resolution, auth,
        mention gates, thread anchoring and media caching all behave
        identically for both. Returns ``None`` for anything that must not
        reach the agent. DM membership commands are executed here (side
        effect) unless ``allow_dm_commands`` is False — edits pass False so
        a corrected command line neither runs twice nor leaks to the agent.

        The caller owns dispatching: a non-None result still needs
        ``handle_message()``.
        """
        if message.actor_id in self._user_cache:
            # try the user cache.
            user = self._user_cache.get(message.actor_id)
        else:
            # get the user and update cache.
            directory_member = await client.get_user(user_id=message.actor_id)
            if directory_member is None:
                return None
            user = directory_member.user
            if user is None:
                return None
            self._user_cache[user.id] = user

        if user is None:
            return None

        if not self._check_auth(user):
            return None

        # Todo: use a function that either reads from cache or gets room kind again.
        if self._room_kinds.get(message.room_id) is None:
            room_viewer_state = await client.get_room(message.room_id)
            if room_viewer_state is None:
                return None
            if room_viewer_state.room is None:
                return None
            self._room_kinds[message.room_id] = (
                room_viewer_state.room.kind or RoomKind.UNSPECIFIED
            )

        room_kind = self._room_kinds.get(message.room_id)
        message_body = message.body or ""

        logger.debug("message_body: %s room_kind: %s", message_body, room_kind)

        # Membership commands ride in over DMs only: they change what the bot
        # listens to and must never reach the agent pipeline or the mention
        # gates.
        if room_kind == RoomKind.DM:
            if allow_dm_commands:
                if await self._handle_dm_command(room_id, message_body):
                    return None
            elif message_body.startswith("/"):
                logger.debug("Chatto: edited DM command %r not re-run", message_body)
                return None

        # Mention gating deliberately covers everything but DMs: in a channel
        # the bot is one of many listeners and must be addressed, whereas a DM
        # is already addressed at it. Chatto has no group rooms — any
        # multi-participant surface is a channel, and a room whose kind the
        # server never set counts as one too (see _is_respond_room). The
        # shared _mentions_me gate keeps this path and the someone-else check
        # below on one definition of "addressed", broadcast handles included.
        if room_kind != RoomKind.DM:
            policy = self._room_policy(room_id)
            if policy == ChannelPolicy.REQUIRE_MENTION and not self._mentions_me(
                message_body
            ):
                logger.debug(
                    "Chatto: dropping unaddressed message from %s (policy %s)",
                    room_id,
                    policy.value,
                )
                return None

            # In an open channel we see every message, including ones plainly
            # aimed at a named colleague. Answering those would be barging in,
            # so acknowledge that we read it and stay quiet. Checked after the
            # bot-mention test above, so a message naming us *and* someone
            # else still counts as ours.
            if (
                policy == ChannelPolicy.OPEN
                and not self._mentions_me(message_body)
                and await self._mentions_someone_else(message_body)
            ):
                logger.info(
                    "Chatto: message addresses someone else, acknowledging only"
                )
                if self.chatto_config.reactions.value:
                    await self.add_reaction(message.room_id, message.id, "🫥")
                return None

        # Thread anchoring — if the incoming message is inside a Chatto thread, we
        # keep that thread by default; otherwise leave thread_id unset so
        # replies land at the root.
        thread_id = (
            thread_root_event_id or None
        )  # we could also take the room id but then, we're in a thread already.
        if not thread_id and room_kind != RoomKind.DM:
            thread_id = message.id

        source = self.build_source(
            chat_id=room_id,
            chat_name=self._room_names.get(message.room_id),
            chat_type=chat_type_for_room_kind(room_kind),
            user_id=message.actor_id,
            user_name=user.login,  # use login, because display_name is changeable by anyone.
            thread_id=thread_id,
            message_id=source_message_id,
            role_authorized=True,
        )

        # prepare a MessageEvent
        message_event = MessageEvent(
            text=message_body,
            source=source,
            message_id=message.id,
            timestamp=message.created_at or datetime.now(UTC),
            raw_message=message,
            reply_to_message_id=message.in_reply_to,
        )
        if message_event.is_command():
            message_event.message_type = MessageType.COMMAND

        # Attachments — download and hand the local cache paths to the gateway,
        # which runs vision enrichment / document extraction off media_urls.
        (
            message_event.media_urls,
            message_event.media_types,
            media_kinds,
        ) = await self._cache_attachments(list(message.attachments))
        if media_kinds:
            # Same precedence as the Teams/Signal adapters: document-context
            # injection gates strictly on DOCUMENT, image handling keys off the
            # per-path image/* MIME regardless of message_type.
            message_event.message_type = self._message_type_for_media_kinds(media_kinds)
        else:
            message_event.message_type = MessageType.TEXT

        logger.debug("Chatto: MessageEvent: %s", message_event)
        return message_event

    async def _forward_reaction(
        self,
        event: RealtimeEvent,
        payload: ReactionPayload,
        *,
        removed: bool,
    ) -> None:
        """Forward a human reaction to the gateway's reaction hook surface.

        The handler is registered by the gateway via ``set_reaction_handler``
        and fans out as ``reaction:added`` / ``reaction:removed`` through the
        HookRegistry.  The dict shape mirrors the Slack adapter's — hook
        consumers are written against that contract, not against a per-platform
        one.  Our own lifecycle reactions (👀/✅/❌) are dropped: forwarding them
        would feed the agent its own markers.
        """
        actor_id = event.actor_id
        if actor_id and self.me and actor_id == self.me.id:
            return
        if not payload.room_id or not payload.message_event_id or not actor_id:
            return

        handler = getattr(self, "_reaction_handler", None)
        if handler is None:
            return

        action = "removed" if removed else "added"
        try:
            await handler(
                {
                    "platform": ChattoConstants.PLATFORM_NAME,
                    "event_name": f"reaction:{action}",
                    "reaction": payload.emoji,
                    "user_id": actor_id,
                    "item_user_id": None,
                    "item_type": "message",
                    "channel_id": payload.room_id,
                    "message_ts": payload.message_event_id,
                    "event_ts": event.id,
                    "raw_event": event,
                },
            )
        except Exception:  # pragma: no cover - the hook contract is non-blocking
            logger.debug("Chatto: reaction hook forwarding failed", exc_info=True)

    async def _handle_realtime_event(self, event: RealtimeEvent) -> None:
        if self._is_seen(event.id):
            return

        if event.actor_id is None:
            return

        logger.debug("EVENT happened: '%s' from %s", event.kind, event.actor_id)

        if (event_payload := event.get("message_posted")) is not None:
            # Self-event filter — the actor_id on the envelope is authoritative
            # (chattolib does NOT filter this itself; see chatto-bridge notes).
            actor_id = event.actor_id
            if actor_id and self.me and actor_id == self.me.id:
                return

            await self._dispatch_message_posted(event_payload)

        elif (edited_payload := event.get("message_edited")) is not None:
            # Same self-event filter: our own streaming edits echo back here.
            # Redeliveries of edits we made are also caught by _mark_seen in
            # edit_message().
            actor_id = event.actor_id
            if actor_id and self.me and actor_id == self.me.id:
                return

            await self._dispatch_message_edited(
                cast(MessageEditedPayload, edited_payload)
            )

        elif event.kind in ("reaction_added", "reaction_removed"):
            reaction_payload = event.get(event.kind)
            if reaction_payload is not None:
                await self._forward_reaction(
                    event,
                    cast(ReactionPayload, reaction_payload),
                    removed=event.kind == "reaction_removed",
                )

        # confirmed:
        elif event.kind in (
            "mention_notification",
            "projection_event",
            "presence_changed",
            "notification_dismissed",
            "room_marked_as_read",
            "user_typing",
            "notification_created",
            "new_direct_message_notification",
            "message_retracted",
        ):
            logger.debug(
                "Chatto: '%s' event received. Not yet implemented or not needed.",
                event.kind,
            )
        else:
            logger.warning("Chatto: unknown event kind: '%s'", event.kind)

    async def _chattolib_event_loop(self) -> None:
        """Event loop using chattolib's stream_events.

        This replaces the manual WebSocket loop with chattolib's high-level
        stream_events() which provides pre-decoded RealtimeEvent objects.
        """
        delay = ChattoConstants.WS_RECONNECT_INITIAL_BACKOFF
        while not self._closing:
            try:
                client = await self._require_chatto_client()

                await self._refresh_rooms()
                logger.info(
                    "Chatto: starting chattolib event stream with %d rooms",
                    len(self._joined_room_ids),
                )

                async for event in stream_events(client):
                    if self._closing:
                        return
                    await self._handle_realtime_event(event)
                # Iterator exited cleanly — treat as a normal close and reconnect
                # with the local backoff (no server hint available).
                logger.info("Chatto: realtime stream ended, reconnecting")
            except asyncio.CancelledError:
                return
            except ChattoRealtimeCloseError as exc:
                if not exc.reconnect:
                    logger.error(
                        "Chatto: realtime closed by server (%s: %s), not reconnecting",
                        exc.code,
                        exc.message,
                    )
                    return
                wait = max(
                    exc.retry_after_ms / 1000.0,
                    ChattoConstants.WS_RECONNECT_INITIAL_BACKOFF,
                )
                logger.warning(
                    "Chatto: realtime closed by server (%s), reconnecting in %.1fs",
                    exc.code,
                    wait,
                )
                delay = (
                    ChattoConstants.WS_RECONNECT_INITIAL_BACKOFF
                )  # server hint supersedes local backoff
                await self._sleep_interruptible(wait)
                continue
            except ChattoRealtimeError as exc:
                if exc.fatal:
                    logger.error(
                        "Chatto: fatal realtime error (%s): %s", exc.code, exc.message
                    )
                    return
                logger.warning(
                    "Chatto: realtime error (%s: %s), reconnecting in %.1fs",
                    exc.code,
                    exc.message,
                    delay,
                )
            except Exception as exc:
                logger.warning(
                    "Chatto: unexpected realtime error: %s, reconnecting in %.1fs",
                    exc,
                    delay,
                )

            if self._closing:
                return

            jitter = delay * 0.2 * random.random()
            await self._sleep_interruptible(delay + jitter)
            delay = min(delay * 2, ChattoConstants.WS_RECONNECT_MAX_BACKOFF)

    async def _sleep_interruptible(self, seconds: float) -> None:
        """Sleep in short slices so disconnect() cancels promptly."""
        end = asyncio.get_running_loop().time() + seconds
        while not self._closing:
            remaining = end - asyncio.get_running_loop().time()
            if remaining <= 0:
                return
            await asyncio.sleep(min(remaining, 0.5))

    def _warn_if_home_channel_unjoined(self, member_ids: set[str]) -> None:
        """Warn once when CHATTO_HOME_CHANNEL names a room the bot is not in.

        Standalone cron delivery posts straight into that room with a fresh
        client and no join logic of its own — without server-side membership
        every proactive send fails there.
        """
        home_id = (self.chatto_config.home_channel.value or "").strip()
        if (
            not home_id
            or home_id in member_ids
            or home_id in self._joined_room_ids
            or self._home_warning_logged
        ):
            return
        self._home_warning_logged = True
        logger.warning(
            "Chatto: CHATTO_HOME_CHANNEL '%s' is not a joined room - cron and "
            "notification delivery will fail until the bot joins it (invite "
            "the account natively in Chatto, or DM it '/join').",
            home_id,
        )

    async def _refresh_rooms(self) -> None:
        """Refresh room list via ConnectRPC, join and seed any newly discovered rooms."""
        client = await self._get_chatto_client()
        if client is None:
            logger.warning("Chatto WS: _refresh_rooms aborted - no client available")
            return

        try:
            rooms_list = await client.list_rooms()
            member_ids: set[str] = set()
            new_room_ids: list[str] = []

            for room_with_state in rooms_list:
                if not room_with_state:
                    continue

                room_obj = room_with_state.room or None
                if not room_obj:
                    continue

                self._room_names[room_obj.id] = room_obj.name
                self._room_kinds[room_obj.id] = room_obj.kind
                if room_obj.universal:
                    self._universal_room_ids.add(room_obj.id)

                if not room_with_state.viewer_state.is_member:
                    continue
                member_ids.add(room_obj.id)
                if room_obj.id not in self._joined_room_ids:
                    new_room_ids.append(room_obj.id)

            # Left via /leave, kicked, deleted: rooms we no longer belong
            # to drop out here — otherwise the next refresh would quietly
            # re-add what /leave just removed.
            stale_room_ids = [
                rid for rid in self._joined_room_ids if rid not in member_ids
            ]
            for rid in stale_room_ids:
                self._joined_room_ids.remove(rid)
            if stale_room_ids:
                logger.info(
                    "Chatto WS: no longer a member of %d room(s): %s",
                    len(stale_room_ids),
                    stale_room_ids,
                )

            self._warn_if_home_channel_unjoined(member_ids)

            if not new_room_ids:
                return

            logger.info(
                "Chatto WS: discovered %d new room(s): %s",
                len(new_room_ids),
                new_room_ids,
            )

            for rid in new_room_ids:
                # Membership came straight from the directory scan
                # (viewer_state.is_member); natively invited rooms need no
                # JoinRoom call — same rule as _run_join.
                if self._is_respond_room(rid):
                    await self._seed_room(rid)
                else:
                    logger.info(
                        "Chatto WS: %s (%s) is on neither mention list -"
                        " joined read-only",
                        self._room_names.get(rid, rid),
                        rid,
                    )
                self._joined_room_ids.append(rid)

            joined_room_names: list[str] = []
            for rid in self._joined_room_ids:
                name = self._room_names[rid]
                if not self._is_respond_room(rid):
                    name += " [read-only]"
                if rid in self._universal_room_ids:
                    name += " [universal]"
                joined_room_names.append(name + " (" + rid + ")")

            logger.info(
                "Chatto WS: currently joined in %d room(s): %s",
                len(self._joined_room_ids),
                ", ".join(joined_room_names),
            )

        except Exception:
            logger.warning("Chatto WS: _refresh_rooms failed", exc_info=True)

        # ------------------------------------------------------------------ #
        # Read state & notification dismissal (best-effort, Chatto-unique)
        # ------------------------------------------------------------------ #
        # Best-effort: mark all joined rooms as read (room_id may be undefined here)
        for _rid in list(self._joined_room_ids):
            try:
                await client.mark_room_as_read(room_id=_rid)
            except Exception:
                logger.debug(
                    "Chatto: mark_room_as_read failed for %s", _rid, exc_info=True
                )
        # Dismissal is server-global — once after the per-room sweep.
        try:
            await client.dismiss_all_notifications()
        except Exception:
            logger.debug("Chatto: dismiss_all_notifications failed", exc_info=True)

    # ------------------------------------------------------------------ #
    # Sending (ConnectRPC — unchanged from polling version)
    # ------------------------------------------------------------------ #

    async def send(
        self,
        chat_id: str,
        content: str,
        reply_to: str | None = None,
        metadata: dict[str, Any] | None = None,
    ) -> SendResult:
        """Send a message to a Chatto room.

        Long messages are split into chunks via ``truncate_message`` and
        each chunk is sent as a separate CreateMessage call.  The first
        chunk's message ID is returned as ``message_id``.

        When ``auto_thread`` is enabled and the incoming message was a
        regular room message (not already in a thread), the first chunk is
        sent as a room message and its ID becomes the thread root. Subsequent
        chunks are sent in that thread. This mirrors Discord's auto_thread
        behavior.

        BasePlatformAdapter override
        """
        if not content:
            return SendResult(success=False, error="Empty message")

        formatted = self.format_message(content)
        chunks = self.truncate_message(formatted, ChattoConstants.MAX_MESSAGE_LENGTH)

        # Thread support — resolve thread_id once
        # DM rooms don't support threads, so skip threading for DMs
        thread_id = (metadata or {}).get("thread_id")
        # Only use reply_to as thread_id if auto_thread is enabled.
        # When auto_thread=false, responses go directly in the room
        # without threading under the incoming message.
        # If we already have thread_id from metadata, keep it (it's the
        # thread root); only use reply_to when we don't already have one.
        if reply_to and self.chatto_config.auto_thread.value and not thread_id:
            thread_id = reply_to
        # Check if this is a DM room — DMs don't support threads
        room_kind = self._room_kinds.get(chat_id)
        is_dm = room_kind == RoomKind.DM
        if is_dm:
            thread_id = None

        # Auto-thread: by default, Chatto creates a thread for replies to room
        # messages (not DMs, not already in a thread). This keeps conversations
        # organized in the room. Can be disabled via extra.auto_thread=false.
        use_auto_thread = (
            self.chatto_config.auto_thread.value and not thread_id and not is_dm
        )

        message_ids: list[str] = []
        last_error: str | None = None
        retryable = False

        client = await self._get_chatto_client()
        if client is None:
            return SendResult(
                success=False, error="Chatto client not available", retryable=True
            )

        for i, chunk in enumerate(chunks):
            try:
                msg_obj = await client.post_message(
                    room_id=chat_id,
                    body=chunk,
                    thread_root_event_id=str(thread_id) if thread_id else "",
                )
            except ChattoError as e:
                last_error = str(e)
                retryable = True
                break
            except Exception as e:
                last_error = str(e)
                retryable = True
                break

            self._mark_seen(msg_obj.id)
            message_ids.append(msg_obj.id)
            # Auto-thread: first chunk becomes the thread root,
            # subsequent chunks go in the thread
            if use_auto_thread and i == 0 and not thread_id:
                thread_id = msg_obj.id

        # Nothing got through at all — report the failure instead of a phantom success.
        if not message_ids:
            return SendResult(
                success=False,
                error=last_error or "Chatto: message could not be sent",
                retryable=retryable,
            )

        first_id = message_ids[0]

        # ------------------------------------------------------------------ #
        # Thread following (best-effort, Chatto-unique)
        # ------------------------------------------------------------------ #
        if thread_id:
            try:
                await client.follow_thread(chat_id, thread_id)
            except Exception:
                logger.debug(
                    "Chatto: follow_thread failed for %s/%s",
                    chat_id,
                    thread_id,
                    exc_info=True,
                )

        # A later chunk failed after earlier ones went out: partial delivery.
        if last_error:
            logger.warning(
                "Chatto: sent %d/%d chunk(s) to %s before failing: %s",
                len(message_ids),
                len(chunks),
                chat_id,
                last_error,
            )

        # raw_response stays unset (dict-shaped per the SendResult contract):
        # gateway consumers such as the cron scheduler call .get() on it, so a
        # chattolib Message here would crash delivery bookkeeping *after* the
        # send already succeeded — the job then falls back to the standalone
        # path and the room sees the message twice.
        return SendResult(success=True, message_id=first_id)

    def format_message(self, content: str) -> str:
        """Normalise outgoing text for Chatto.

        Chatto renders Markdown natively, so there is nothing to escape or
        translate — the only transformations here are the ones that measurably
        render wrong: CRLF line endings (which show up as stray blank lines)
        and runs of more than two blank lines.

        BasePlatformAdapter override
        """
        if not content:
            return content
        normalised = content.replace("\r\n", "\n").replace("\r", "\n")
        while "\n\n\n\n" in normalised:
            normalised = normalised.replace("\n\n\n\n", "\n\n\n")
        return normalised

    async def edit_message(
        self,
        chat_id: str,
        message_id: str,
        content: str,
        *,
        finalize: bool = False,
    ) -> SendResult:
        """Edit a message we previously sent, via MessageService/UpdateMessage.

        The stream consumer drives streaming replies through this: without the
        override the base class reports "Not supported" and every incremental
        update arrives as a *new* message.

        ``finalize`` is a no-op for Chatto — an edit is an edit here, there is
        no in-progress card state to close out (hence no
        ``REQUIRES_EDIT_FINALIZE``).

        Content that exceeds the per-message limit is refused rather than
        silently truncated, so the caller falls back to ``send()``, which
        splits across messages.

        BasePlatformAdapter override
        """
        if not message_id:
            return SendResult(success=False, error="Chatto: no message id to edit")
        if not content:
            return SendResult(success=False, error="Empty message")

        formatted = self.format_message(content)
        if len(formatted) > ChattoConstants.MAX_MESSAGE_LENGTH:
            # Refuse instead of truncating: the caller's fallback path splits.
            return SendResult(
                success=False,
                error=(
                    f"Chatto: edit exceeds {ChattoConstants.MAX_MESSAGE_LENGTH} "
                    f"chars ({len(formatted)})"
                ),
            )

        client = await self._get_chatto_client()
        if client is None:
            return SendResult(
                success=False, error="Chatto client not available", retryable=True
            )

        try:
            msg = await client.update_message(
                room_id=str(chat_id),
                event_id=str(message_id),
                body=formatted,
            )
        except ChattoError as e:
            logger.warning("Chatto: UpdateMessage failed for %s: %s", message_id, e)
            return SendResult(success=False, error=str(e), retryable=True)
        except Exception as e:
            logger.warning("Chatto: UpdateMessage error for %s: %s", message_id, e)
            return SendResult(success=False, error=str(e), retryable=False)

        # Our own edit comes back as a message_edited event; mark it seen so it
        # is never mistaken for inbound traffic.
        edited_id = msg.id or str(message_id)
        self._mark_seen(edited_id)
        return SendResult(success=True, message_id=edited_id)

    async def delete_message(self, chat_id: str, message_id: str) -> bool:
        """Delete a message via MessageService/DeleteMessage.

        Used by the stream consumer's fresh-final cleanup (removing a preview
        message once the completed reply has been sent) and by the ephemeral
        reply TTL.

        BasePlatformAdapter override
        """
        if not chat_id or not message_id:
            return False
        client = await self._get_chatto_client()
        if client is None:
            logger.warning("Chatto: DeleteMessage — client unavailable")
            return False
        try:
            return bool(
                await client.delete_message(
                    room_id=str(chat_id),
                    event_id=str(message_id),
                )
            )
        except ChattoError as e:
            logger.warning("Chatto: DeleteMessage failed for %s: %s", message_id, e)
            return False
        except Exception as e:
            logger.warning("Chatto: DeleteMessage error for %s: %s", message_id, e)
            return False

    async def create_handoff_thread(
        self,
        parent_chat_id: str,
        name: str,
    ) -> str | None:
        """Anchor a session handoff in a fresh thread under *parent_chat_id*.

        Chatto threads hang off a message, not off the room, so we post a seed
        message and hand its ID back as the thread root — the same shape the
        Slack adapter uses.  DMs don't support threads, so they get ``None``
        and the watcher keeps delivering into the DM itself.

        BasePlatformAdapter override
        """
        if not parent_chat_id:
            return None
        if self._room_kinds.get(parent_chat_id) == RoomKind.DM:
            logger.debug("Chatto: handoff thread skipped — %s is a DM", parent_chat_id)
            return None

        client = await self._get_chatto_client()
        if client is None:
            logger.warning("Chatto: handoff thread — client unavailable")
            return None

        try:
            msg = await client.post_message(
                room_id=str(parent_chat_id),
                body=f"🧵 Hermes handoff — **{(name or 'session').strip()[:80]}**",
            )
        except Exception as e:
            logger.warning(
                "Chatto: handoff thread seed-post failed for room %s: %s",
                parent_chat_id,
                e,
            )
            return None

        seed_id = msg.id
        if not seed_id:
            logger.warning("Chatto: handoff thread seed-post returned no message id")
            return None

        self._mark_seen(seed_id)
        try:
            await client.follow_thread(str(parent_chat_id), seed_id)
        except Exception:
            logger.debug(
                "Chatto: follow_thread failed for handoff %s/%s",
                parent_chat_id,
                seed_id,
                exc_info=True,
            )
        return seed_id

    # Overridden from BaseAdapter:
    async def send_typing(self, chat_id: str, metadata=None) -> None:
        """Start a persistent typing indicator for a room.

        Sends a typing ping every 10 seconds (Chatto's indicator likely
        lasts ~8-10s).  The background loop runs until ``stop_typing()``
        is called or the task is cancelled.

        BasePlatformAdapter override
        """
        if chat_id in self._typing_tasks:
            return  # already running

        async def _typing_loop() -> None:
            try:
                while True:
                    try:
                        client = await self._get_chatto_client()
                        if client is None:
                            return
                        await client.update_typing_indicator(room_id=str(chat_id))
                    except asyncio.CancelledError:
                        return
                    except Exception:
                        logger.debug(
                            "Chatto: typing indicator refresh failed for %s",
                            chat_id,
                            exc_info=True,
                        )
                    await asyncio.sleep(10)
            except asyncio.CancelledError:
                pass
            finally:
                self._typing_tasks.pop(chat_id, None)

        self._typing_tasks[chat_id] = asyncio.create_task(_typing_loop())

    async def stop_typing(self, chat_id: str) -> None:
        """Stop the persistent typing indicator for a room.

        BasePlatformAdapter override
        """
        task = self._typing_tasks.pop(chat_id, None)
        if task:
            task.cancel()
            try:
                await task
            except (asyncio.CancelledError, Exception):
                logger.debug("Chatto: typing task ended for %s", chat_id, exc_info=True)

    async def get_chat_info(self, chat_id: str) -> dict[str, Any]:
        """Get information about a chat/room.

        BasePlatformAdapter override
        """
        name = self._room_names.get(chat_id, chat_id)
        kind = self._room_kinds.get(chat_id)
        return {
            "name": name,
            "type": chat_type_for_room_kind(kind).value,
        }

    # ------------------------------------------------------------------ #
    # Reactions
    # ------------------------------------------------------------------ #

    @staticmethod
    def _emoji_to_shortcode(emoji: str) -> str:
        """Convert a unicode emoji to a Chatto shortcode name.

        If the emoji is already a shortcode (no unicode mapping found),
        return it as-is.
        """
        shortcode = ChattoConstants.EMOJI_TO_SHORTCODE.get(emoji)
        if shortcode:
            return shortcode
        # Already a shortcode like "thumbsup" — return as-is
        return emoji

    async def add_reaction(self, room_id: str, message_id: str, emoji: str) -> bool:
        """Add a reaction to a message via MessageService/AddReaction.

        BasePlatformAdapter override
        """
        shortcode = self._emoji_to_shortcode(emoji)
        client = await self._get_chatto_client()
        if client is None:
            logger.warning("Chatto: AddReaction — client unavailable")
            return False
        try:
            result = await client.add_reaction(
                room_id=room_id,
                message_event_id=message_id,
                emoji=shortcode,
            )
            return result
        except ChattoError as e:
            logger.warning("Chatto: AddReaction failed: %s", e)
            return False
        except Exception as e:
            logger.warning("Chatto: AddReaction error: %s", e)
            return False

    async def remove_reaction(self, chat_id: str, message_id: str, emoji: str) -> bool:
        """Remove a reaction from a message via MessageService/RemoveReaction.

        BasePlatformAdapter override
        """
        shortcode = self._emoji_to_shortcode(emoji)
        client = await self._get_chatto_client()
        if client is None:
            logger.warning("Chatto: RemoveReaction — client unavailable")
            return False
        try:
            result = await client.remove_reaction(
                room_id=str(chat_id),
                message_event_id=str(message_id),
                emoji=shortcode,
            )
            return result
        except ChattoError as e:
            logger.warning("Chatto: RemoveReaction failed: %s", e)
            return False
        except Exception as e:
            logger.warning("Chatto: RemoveReaction error: %s", e)
            return False

    # ------------------------------------------------------------------ #
    # DM initiation (Chatto-unique)
    # ------------------------------------------------------------------ #

    async def start_dm(self, user_id: str) -> str | None:
        """Start a direct message with a user via RoomService/StartDM.

        Returns the room ID on success, or None on failure.

        BasePlatformAdapter override
        """
        if not user_id:
            return None
        client = await self._get_chatto_client()
        if client is None:
            return None
        try:
            room = await client.start_dm(participant_ids=[str(user_id)])
            self._room_names[room.id] = room.name
            self._room_kinds[room.id] = room.kind
            return room.id
        except ChattoError as e:
            logger.debug("Chatto: StartDM failed: %s", e)
            return None
        except Exception as e:
            logger.debug("Chatto: StartDM error: %s", e)
            return None

    # ------------------------------------------------------------------ #
    # Room creation (Chatto-unique)
    # ------------------------------------------------------------------ #

    async def create_room(
        self,
        name: str,
        description: str = "",
        group_id: str = "",
        universal: bool = True,
    ) -> str | None:
        """Create an ad-hoc room via RoomService/CreateRoom.

        Returns the room ID on success, or None on failure.

        BasePlatformAdapter override
        """
        client = await self._get_chatto_client()
        if client is None:
            return None
        try:
            room = await client.create_room(
                name=name,
                group_id=group_id or "",
                description=description,
                universal=universal,
            )
            rid = str(room.id) if room else ""
            if rid:
                self._room_names[rid] = room.name
                self._room_kinds[rid] = room.kind
                return rid
            logger.debug("Chatto: CreateRoom returned no room id")
            return None
        except ChattoError as e:
            logger.debug("Chatto: CreateRoom failed: %s", e)
            return None
        except Exception as e:
            logger.debug("Chatto: CreateRoom error: %s", e)
            return None

    # ------------------------------------------------------------------ #
    # Processing lifecycle hooks (reactions-based, like Discord)
    # ------------------------------------------------------------------ #

    def _event_room_and_message_id(self, event: MessageEvent) -> tuple[str, str]:
        """Extract room_id and message_id from a MessageEvent."""
        message_id = event.message_id or ""
        return event.source.chat_id, message_id

    async def on_processing_start(self, event: MessageEvent) -> None:
        """Record the turn as open, then add an 👀 (eyes) reaction.

        The record is what lets an edit of this very message be recognized as
        a mid-run correction. It must be maintained even when reactions are
        disabled — tracking and decorating are independent concerns.

        BasePlatformAdapter override
        """
        session_key = (
            self._session_key_for(event.source) if event.source is not None else ""
        )
        if session_key and event.message_id:
            self._processing[session_key] = str(event.message_id)

        if not self.chatto_config.reactions.value:
            return

        chat_id, message_id = self._event_room_and_message_id(event)
        if not chat_id or not message_id:
            # Routine, not a fault: the gateway runs agent-initiated turns
            # (heartbeat polls, goal continuations) through the same pipeline
            # with message_id=None, and there is no inbound message to mark.
            logger.debug(
                "Chatto: nothing to react to (chat_id=%r, message_id=%r)",
                chat_id,
                message_id,
            )
            return
        await self.add_reaction(chat_id, message_id, "👀")

    async def on_processing_complete(
        self,
        event: MessageEvent,
        outcome: ProcessingOutcome,
    ) -> None:
        """Close the turn's record, then swap 👀 for ✅/❌/🚫.

        Fires for every outcome, including CANCELLED (mid-run edit
        correction) — this is what re-arms `_processing` before the corrected
        turn is dispatched.

        BasePlatformAdapter override
        """
        session_key = (
            self._session_key_for(event.source) if event.source is not None else ""
        )
        if session_key and event.message_id:
            self._processing.pop(session_key, None)

        if not self.chatto_config.reactions.value:
            return
        chat_id, message_id = self._event_room_and_message_id(event)
        if not chat_id or not message_id:
            return
        # Remove the processing eyes reaction
        await self.remove_reaction(chat_id, message_id, "👀")
        # Add the outcome reaction
        if outcome == ProcessingOutcome.SUCCESS:
            await self.add_reaction(chat_id, message_id, "✅")
        elif outcome == ProcessingOutcome.FAILURE:
            await self.add_reaction(chat_id, message_id, "❌")
        elif outcome == ProcessingOutcome.CANCELLED:
            await self.add_reaction(chat_id, message_id, "🚫")

    # ------------------------------------------------------------------ #
    # Asset upload (chunked)
    # ------------------------------------------------------------------ #

    async def _upload_asset(self, room_id: str, file_path: str) -> str | None:
        """Upload a file via the chunked AssetUploadService.

        Returns the asset ID on success, or None on failure.
        """
        try:
            file_data = await asyncio.to_thread(_read_file_bytes, file_path)
        except Exception as e:
            logger.error("Chatto: failed to read file %s — %s", file_path, e)
            return None

        if not file_data:
            logger.error("Chatto: file %s is empty", file_path)
            return None

        file_size = len(file_data)
        file_name = os.path.basename(file_path)
        mime_type = mimetypes.guess_type(file_path)[0] or "application/octet-stream"
        sha256_hash = hashlib.sha256(file_data).hexdigest()

        client = await self._get_chatto_client()
        if client is None:
            logger.error("Chatto: upload aborted - no client available")
            return None
        try:
            # Step 1: Create upload session
            upload = await client.create_upload(
                room_id=room_id,
                filename=file_name,
                size=file_size,
                sha256=sha256_hash,
                content_type=mime_type,
            )
            # AssetUpload names this upload_id, not id — reading it through an
            # untyped getattr default is what let the mismatch reach production.
            upload_id = upload.upload_id
            if not upload_id:
                logger.error("Chatto: CreateUpload returned no upload ID")
                return None

            # Step 2: Upload chunks
            offset = 0
            while offset < file_size:
                chunk = file_data[offset : offset + ChattoConstants.UPLOAD_CHUNK_SIZE]
                chunk_sha256 = hashlib.sha256(chunk).hexdigest()
                await client.upload_chunk(
                    upload_id=upload_id,
                    offset=offset,
                    content=chunk,
                    chunk_sha256=chunk_sha256,
                )
                offset += len(chunk)

            # Step 3: Complete upload
            upload, asset = await client.complete_upload(upload_id=upload_id)
            if not asset:
                logger.error("Chatto: CompleteUpload returned no asset")
                return None

            logger.info(
                "Chatto: uploaded %s as asset %s (%d bytes)",
                file_name,
                asset.id,
                file_size,
            )
            return asset.id

        except ChattoError as e:
            logger.error("Chatto: upload failed: %s", e)
            return None
        except Exception as e:
            logger.error("Chatto: upload error: %s", e)
            return None

    async def _post_attachment_message(
        self,
        chat_id: str,
        asset_ids: list[str],
        caption: str | None,
        reply_to: str | None,
        metadata: dict[str, Any] | None,
    ) -> SendResult:
        """Post one message carrying already-uploaded assets."""
        thread_id = (metadata or {}).get("thread_id")
        if reply_to:
            thread_id = reply_to

        client = await self._get_chatto_client()
        if client is None:
            return SendResult(
                success=False, error="Chatto client not available", retryable=True
            )
        try:
            msg = await client.post_message(
                room_id=str(chat_id),
                body=self.format_message(caption) if caption else "",
                attachment_asset_ids=asset_ids,
                thread_root_event_id=str(thread_id) if thread_id else "",
            )
            self._mark_seen(msg.id)
            return SendResult(success=True, message_id=msg.id)
        except ChattoError as e:
            return SendResult(success=False, error=str(e), retryable=True)
        except Exception as e:
            return SendResult(success=False, error=str(e), retryable=False)

    async def _send_local_file_as_attachment(
        self,
        chat_id: str,
        file_path: str,
        caption: str | None,
        reply_to: str | None,
        metadata: dict[str, Any] | None,
        *,
        kind: str,
    ) -> SendResult:
        """Upload a local file and post it as a native Chatto attachment.

        Shared by ``send_image_file``/``send_document``/``send_video``/
        ``send_voice`` — the upload mechanics are identical, only the wording of
        the failure notice differs.  On failure we send that notice as text and
        never the host path (it leaks the Hermes home layout).
        """
        notice = f"⚠️ Couldn't deliver the {kind} attachment."

        safe_path = self.validate_media_delivery_path(file_path)
        if not safe_path:
            logger.warning(
                "[%s] send %s: unsafe path %s",
                self.name,
                kind,
                file_path,
            )
            text = f"{caption}\n{notice}" if caption else notice
            return await self.send(chat_id, text, reply_to=reply_to, metadata=metadata)

        asset_id = await self._upload_asset(str(chat_id), safe_path)
        if not asset_id:
            logger.warning(
                "[%s] send %s: upload failed for %s",
                self.name,
                kind,
                safe_path,
            )
            text = f"{caption}\n{notice}" if caption else notice
            return await self.send(chat_id, text, reply_to=reply_to, metadata=metadata)

        return await self._post_attachment_message(
            chat_id,
            [asset_id],
            caption,
            reply_to,
            metadata,
        )

    async def send_image_file(
        self,
        chat_id: str,
        image_path: str,
        caption: str | None = None,
        reply_to: str | None = None,
        metadata: dict[str, Any] | None = None,
        **kwargs,
    ) -> SendResult:
        """Send a local image file via the chunked upload API.

        The parameter is ``image_path``, not ``file_path``: every caller passes
        it by keyword (``gateway/run.py:22354``, ``:22470``, and the base class's
        own ``send_multiple_images`` file:// branch), so a renamed parameter
        makes each of those raise TypeError and silently degrade to a text
        notice.

        BasePlatformAdapter override
        """
        return await self._send_local_file_as_attachment(
            chat_id,
            image_path,
            caption,
            reply_to,
            metadata,
            kind="image",
        )

    async def send_document(
        self,
        chat_id: str,
        file_path: str,
        caption: str | None = None,
        file_name: str | None = None,
        reply_to: str | None = None,
        metadata: dict[str, Any] | None = None,
        **kwargs,
    ) -> SendResult:
        """Send a local file as a native Chatto attachment.

        ``file_name`` exists in the base-class signature and is accepted for
        compatibility, but Chatto takes the recipient-visible filename from
        the upload session (derived from the local path); failures are logged
        and noticed by ``_send_local_file_as_attachment`` itself.

        BasePlatformAdapter override
        """
        return await self._send_local_file_as_attachment(
            chat_id,
            file_path,
            caption,
            reply_to,
            metadata,
            kind="file",
        )

    async def send_video(
        self,
        chat_id: str,
        video_path: str,
        caption: str | None = None,
        reply_to: str | None = None,
        metadata: dict[str, Any] | None = None,
        **kwargs,
    ) -> SendResult:
        """Send a local video as a native Chatto attachment.

        Chatto transcodes and plays it inline.

        BasePlatformAdapter override
        """
        return await self._send_local_file_as_attachment(
            chat_id,
            video_path,
            caption,
            reply_to,
            metadata,
            kind="video",
        )

    async def send_voice(
        self,
        chat_id: str,
        audio_path: str,
        caption: str | None = None,
        reply_to: str | None = None,
        metadata: dict[str, Any] | None = None,
        **kwargs,
    ) -> SendResult:
        """Send a local audio file as a native Chatto attachment.

        Chatto has no dedicated voice-bubble type, so this is an ordinary audio
        attachment — still far better than the base class's text notice.

        BasePlatformAdapter override
        """
        return await self._send_local_file_as_attachment(
            chat_id,
            audio_path,
            caption,
            reply_to,
            metadata,
            kind="audio",
        )

    async def send_image(
        self,
        chat_id: str,
        image_url: str,
        caption: str | None = None,
        reply_to: str | None = None,
        metadata: dict[str, Any] | None = None,
    ) -> SendResult:
        """Send an image to a Chatto room.

        Materialises the URL (size-capped download, like every inbound
        attachment) and uploads it as a native attachment. Falls back to the
        plain URL as a link — Chatto renders link previews — when the URL
        cannot be materialised or the post after a successful upload fails.
        An upload failure needs no fallback on top: the text notice of
        ``_send_local_file_as_attachment`` has already gone out.

        BasePlatformAdapter override
        """
        link_text = f"{caption}\n{image_url}" if caption else image_url
        path, is_temp = await self._materialise_image(image_url)
        if path is not None:
            try:
                result = await self._send_local_file_as_attachment(
                    chat_id, path, caption, reply_to, metadata, kind="image"
                )
            finally:
                if is_temp:
                    try:
                        os.unlink(path)
                    except OSError:
                        pass
            if result.success:
                return result

        return await self.send(chat_id, link_text, reply_to=reply_to, metadata=metadata)

    async def _materialise_image(self, image_url: str) -> tuple[str | None, bool]:
        """Resolve one ``send_multiple_images`` entry to a local file path.

        Accepts ``http(s)://`` URLs (downloaded to a temp file), ``file://``
        URIs and bare paths.  Returns ``(path, is_temp)`` — the caller unlinks
        when ``is_temp``.          ``(None, False)`` means the entry is unusable.
        """
        if image_url.startswith(("http://", "https://")):
            ext = os.path.splitext(urlsplit(image_url).path)[1] or ".png"
            tmp_fd, tmp_path = tempfile.mkstemp(suffix=ext, prefix="chatto_img_")
            os.close(tmp_fd)
            try:
                data = await self._download_attachment_bytes(image_url)
                await asyncio.to_thread(_write_file_bytes, tmp_path, data)
            except Exception as e:
                logger.warning("Chatto: image download failed for %s: %s", image_url, e)
                try:
                    os.unlink(tmp_path)
                except OSError:
                    pass
                return None, False
            return tmp_path, True

        local = image_url
        if local.startswith("file://"):
            local = unquote(urlsplit(local).path)
        return self.validate_media_delivery_path(local), False

    async def send_multiple_images(
        self,
        chat_id: str,
        images: list[tuple[str, str]],
        metadata: dict[str, Any] | None = None,
        human_delay: float = 0.0,
    ) -> None:
        """Send a batch of images as ONE message with several attachments.

        The base implementation posts each image separately; a Chatto message
        carries a list of attachment assets, so a batch belongs in a single
        message (and a single notification).

        ``human_delay`` is ignored deliberately — there is only one outbound
        call to pace.  Entries that can't be fetched are dropped with a warning;
        if nothing survives, we fall back to the base class so the user still
        gets the links.

        BasePlatformAdapter override
        """
        if len(images or []) < 2:
            await super().send_multiple_images(
                chat_id,
                images,
                metadata=metadata,
                human_delay=human_delay,
            )
            return

        asset_ids: list[str] = []
        captions: list[str] = []
        for image_url, alt_text in images:
            path, is_temp = await self._materialise_image(image_url)
            if not path:
                logger.warning("Chatto: skipping unusable image %s", image_url)
                continue
            try:
                asset_id = await self._upload_asset(str(chat_id), path)
            finally:
                if is_temp:
                    try:
                        os.unlink(path)
                    except OSError:
                        pass
            if not asset_id:
                logger.warning("Chatto: upload failed for image %s", image_url)
                continue
            asset_ids.append(asset_id)
            if alt_text:
                captions.append(alt_text)

        if not asset_ids:
            logger.warning(
                "Chatto: no image survived upload, falling back to per-image delivery",
            )
            await super().send_multiple_images(
                chat_id,
                images,
                metadata=metadata,
                human_delay=human_delay,
            )
            return

        if len(asset_ids) < len(images):
            logger.warning(
                "Chatto: sending %d of %d images — the rest could not be uploaded",
                len(asset_ids),
                len(images),
            )

        await self._post_attachment_message(
            chat_id,
            asset_ids,
            "\n".join(captions) or None,
            None,
            metadata,
        )


# ---------------------------------------------------------------------------
# Cron / out-of-process delivery
# ---------------------------------------------------------------------------


async def hermes_standalone_sender_fn(
    pconfig: PlatformConfig,
    chat_id: str,
    message: str,
    *,
    thread_id=None,
    media_files=None,
    force_document=False,
) -> SendResult:
    """Deliver a message to Chatto without a running gateway adapter. Do not modify signature.

    Used by cron / scheduled routines that run out-of-process. Creates a
    short-lived chattolib client, posts, and closes.
    """
    chatto_config: ChattoConfiguration = ChattoConfiguration(pconfig=pconfig)

    # Create a temporary client for standalone sending — we need a base URL plus
    # either a token or a full login/password pair.
    has_credentials = bool(
        chatto_config.token.value
        or (chatto_config.login.value and chatto_config.password.value),
    )
    if not chatto_config.base_url.value or not has_credentials:
        return SendResult(
            success=False, error="Chatto: base URL or credentials missing"
        )

    client: ChattoClient
    try:
        if chatto_config.token.value:
            client = ChattoClient(
                base_url=chatto_config.base_url.value, token=chatto_config.token.value
            )
        else:
            client = await ChattoClient.login(
                base_url=chatto_config.base_url.value,
                login=chatto_config.login.value,
                password=chatto_config.password.value,
            )
    except Exception as exc:
        return SendResult(success=False, error=f"Chatto login failed: {exc}")

    try:
        kwargs: dict[str, Any] = {}
        if chatto_config.auto_thread.value and thread_id:
            kwargs["thread_root_event_id"] = thread_id
        if media_files and media_files.get("attachment_asset_ids"):
            kwargs["attachment_asset_ids"] = list(media_files["attachment_asset_ids"])
        try:
            posted = await client.post_message(chat_id, message, **kwargs)
        except Exception as exc:
            return SendResult(success=False, error=str(exc))
        return SendResult(success=True, message_id=posted.id)
    finally:
        try:
            await client.close()
        except Exception as exc:
            logger.warning(
                "Chatto standalone: error closing short-lived client (perhaps already closed): %s",
                exc,
            )


# How similar an ``extra`` key must be to a declared config_key before the
# unknown-key check reads it as a likely typo or renamed field.
_NEAR_MISS_RATIO = 0.75


def _warn_on_unknown_extra_keys(config: PlatformConfig) -> None:
    """Warn about ``extra`` keys that look like misspelled config fields.

    A typo'd key silently resolves to the default otherwise — the warning is
    the only thing telling the user their ``require_mention_channles`` never
    reached us. Only near-matches against our declared config_keys are
    flagged (difflib similarity): keys that resemble nothing of ours are
    either placed there by the Hermes gateway itself (the shared-key loop in
    load_gateway_config() bridges reply_in_thread & co. into every platform's
    extra, hardcoded inline upstream — nothing to import) or are deliberate
    pass-throughs, and flagging those would just train users to ignore us.
    Internal markers (``_enabled_explicit``) are skipped outright.
    """
    extra: dict[str, Any] = getattr(config, "extra", None) or {}
    known = [field.config_key for field in ChattoConfiguration.fields()]
    for key in sorted(extra):
        if key.startswith("_") or key in known:
            continue
        best = max(known, key=lambda k: SequenceMatcher(None, key, k).ratio())
        if SequenceMatcher(None, key, best).ratio() >= _NEAR_MISS_RATIO:
            logger.warning(
                "Chatto: 'extra' key '%s' matches no config field — did you mean '%s'?",
                key,
                best,
            )


def hermes_validate_config(config: PlatformConfig) -> bool:
    """Check whether Chatto Plugin is configured.

    Function name should be the same as register argument name with "hermes_" prefix, so we
    know that it is needed for plugin register(). Do not change signature.
    Takes ``config``. Compare to hermes_is_connected().
    """
    chatto_config = ChattoConfiguration(pconfig=config)
    _warn_on_unknown_extra_keys(config)

    if (
        len(chatto_config.allowed_users.value) > 0
        and chatto_config.allow_all_users.value
    ):
        logger.error(
            "Chatto: Conflicting configuration. Either use 'allowed_users' or 'allow_all_users' but not both."
        )
        return False

    require_channels = set(chatto_config.require_mention_rooms.value)
    optional_channels = set(chatto_config.optional_mention_rooms.value)
    overlap = sorted(require_channels & optional_channels)
    if overlap:
        logger.error(
            "Chatto: Conflicting configuration. Room(s) %s are on both "
            "'require_mention_rooms' and 'optional_mention_rooms' — "
            "each room must appear in at most one of them.",
            ", ".join(overlap),
        )
        return False

    # base_url always resolves (it defaults to ChattoHQ), so the only real
    # question is whether any credentials came in.
    if (chatto_config.token.value is not None) or (
        chatto_config.login.value and chatto_config.password.value
    ):
        return True
    logger.error("Chatto: Minimally, either token or login/password must be set.")
    return False


def hermes_check_fn() -> bool:
    """Report whether the vendored chattolib dependency can be imported."""
    try:
        from chattolib import (
            client,  # noqa: F401 — vendored dependency probe
        )

        return True
    except ImportError:
        return False


# ---------------------------------------------------------------------------
# is_connected probe
# ---------------------------------------------------------------------------


def hermes_is_connected(config: PlatformConfig) -> bool:
    """Report whether the Chatto platform is configured and enabled.

    The name is fixed by the register() contract, but despite what it
    suggests this does not open a connection — it validates configuration
    only (see :func:`hermes_validate_config`); the gateway probes real
    connectivity through ``connect()``.
    """
    return bool(hermes_validate_config(config) and config.enabled)


def hermes_setup_fn() -> None:
    """Interactive setup wizard for Chatto. Is called by and only works in Hermes CLI context.

    Function name should be the same as register argument name with "hermes_" prefix, so we
    know that it is needed for plugin register().
    """
    from hermes_cli.setup import (
        print_success,
        prompt,
        prompt_yes_no,
        save_env_value,
    )

    url = prompt(
        "Chatto server URL (e.g. https://chat.example.com) or leave blank for default ChattoHQ on chat.chatto.run:"
    )
    if url:
        save_env_value(ChattoConfiguration.base_url.env_name, url)

    login = prompt("Chatto login (username):")
    if login:
        save_env_value(ChattoConfiguration.login.env_name, login)

    password = prompt("Chatto password:", password=True)
    if password:
        save_env_value(ChattoConfiguration.password.env_name, password)

    home = prompt("Home room ID for notifications (or empty):")
    if home:
        save_env_value(ChattoConfiguration.home_channel.env_name, home)

    allow_all = prompt_yes_no("Allow all users to talk? (true/false):")
    if allow_all:
        save_env_value(ChattoConfiguration.allow_all_users.env_name, str(allow_all))
    print_success("\n✓ Chatto configured. Restart the gateway to activate.")


def hermes_env_enablement_fn() -> dict | None:
    """Seed PlatformConfig.extra from env vars.

    Returns a dict compatible with the PlatformConfig merge hook (or None
    when no env-provided values are present).

    Called by the platform registry during load_gateway_config().
    Return None when the platform isn't minimally configured — the
    caller then skips auto-enabling. Return a dict to seed extras.

    The special 'home_channel' key is extracted and becomes a proper
    HomeChannel dataclass on the PlatformConfig; every other key is
    merged into PlatformConfig.extra.

    Function name should be the same as register argument name with "hermes_" prefix, so we
    know that it is needed for plugin register().
    """
    # Seed keys must be the config.yaml "extra" keys (config_key), NOT the env
    # var names — ChattoConfiguration reads extra[config_key].
    seed: dict[str, Any] = {
        ChattoConfiguration.base_url.field_name: (
            os.getenv(ChattoConfiguration.base_url.env_name)
            or ChattoClient.DEFAULT_BASE_URL
        ).strip(),
    }

    for field in ChattoConfiguration.fields():
        if field.field_name == ChattoConfiguration.base_url.field_name:
            continue
        env_value = os.getenv(field.env_name)
        if env_value:
            seed[field.config_key] = env_value.strip()

    logger.debug(
        "seed: %s", {k: v for k, v in seed.items() if k not in ("token", "password")}
    )

    return seed


# ---------------------------------------------------------------------------
# Plugin registration entry point
# ---------------------------------------------------------------------------

# What each capability is called in the startup banner, keyed by the method
# that implements it. Derived from real overrides rather than hard-coded, so
# dropping a method drops its claim from the log instead of leaving a lie.
_CAPABILITY_LABELS = {
    "send": "text",
    "send_image_file": "images",
    "send_multiple_images": "image batches (bundled into one message)",
    "send_video": "video",
    "send_voice": "voice messages",
    "send_document": "documents",
    "add_reaction": "reactions",
    "edit_message": "message editing",
    "delete_message": "message deletion",
    "send_typing": "typing indicators",
    "create_handoff_thread": "threads",
    "start_dm": "direct messages",
    "create_room": "room creation",
}


def _capabilities() -> list[str]:
    """Name the things this adapter genuinely implements itself.

    A capability counts only when ChattoAdapter overrides the base method —
    inheriting BasePlatformAdapter's fallback means the feature is not
    natively supported, and announcing it would mislead.
    """
    found = [
        label
        for name, label in _CAPABILITY_LABELS.items()
        if getattr(ChattoAdapter, name, None)
        is not getattr(BasePlatformAdapter, name, None)
    ]
    if ChattoAdapter.supports_code_blocks:
        found.append("code blocks")
    if ChattoAdapter.supports_status_text:
        found.append("custom status text")
    found.append("presence (refreshed while connected)")
    return found


def register(ctx) -> None:
    """Plugin entry point — called by the Hermes plugin system."""
    logger.info("Registering Chatto platform plugin on Hermes Agent")

    for capability in _capabilities():
        logger.info("Chatto capability: %s", capability)

    ctx.register_platform(
        name=ChattoConstants.PLATFORM_NAME,  # this will be the config.yaml key.
        label=ChattoConstants.PLATFORM_LABEL,
        adapter_factory=hermes_adapter_factory,
        check_fn=hermes_check_fn,
        validate_config=hermes_validate_config,
        is_connected=hermes_is_connected,
        install_hint=ChattoConstants.INSTALL_HINT,
        env_enablement_fn=hermes_env_enablement_fn,
        setup_fn=hermes_setup_fn,
        cron_deliver_env_var=ChattoConfiguration.home_channel.env_name,
        standalone_sender_fn=hermes_standalone_sender_fn,
        allowed_users_env=ChattoConfiguration.allowed_users.env_name,
        allow_all_env=ChattoConfiguration.allow_all_users.env_name,
        max_message_length=ChattoConstants.MAX_MESSAGE_LENGTH,
        emoji="😺",
        allow_update_command=True,
        pii_safe=False,
        platform_hint=(
            "Using the 'Hermes Chatto Platform Plugin' you connect to a Chatto server. "
            "Authorized admins and users will contact you and call you his Hermes Agent. They are "
            "natural persons and thus responsible for what they do in terms of rights. You compute "
            "on their behalf. They _may_ address you by @-mentioning your name. If configured, "
            "you also react without a @-mention. Direct messages reach you without a mention."
            "Keep responses conversational. Markdown is supported. "
            "Include MEDIA:/absolute/path/to/file in your response to refer to our local files. Images "
            "(.png, .jpg, .gif, .webp) arrive as inline pictures, videos (.mp4, .mov, .webm) as "
            "video attachments, audio as a voice bubble, anything else as a downloadable document. "
            "Do NOT use markdown image syntax for local files. Local files always go through MEDIA:. "
            "Several images in one response are bundled into a single message. "
        ),
    )