/tests/tools/test_send_message_tool.py

"""Tests for tools/send_message_tool.py."""

import asyncio
import json
import os
import sys
from types import ModuleType, SimpleNamespace
from unittest.mock import AsyncMock, MagicMock, patch

import pytest

# python-telegram-bot is an optional dep — skip the entire module when
# it isn't installed (e.g. CI bare env). Tests that patch telegram.Bot
# or call _send_telegram need it; tests for other platforms don't but
# keeping the whole file consistent is simpler.
_HAS_TELEGRAM = pytest.importorskip("telegram", reason="python-telegram-bot not installed") is not None


@pytest.fixture(autouse=True)
def _reset_signal_scheduler():
    """Drop the process-wide attachment scheduler so each test gets a
    fresh token bucket."""
    from gateway.platforms.signal_rate_limit import _reset_scheduler
    _reset_scheduler()
    yield
    _reset_scheduler()

from gateway.config import Platform
from tools.send_message_tool import (
    _is_telegram_thread_not_found,
    _parse_target_ref,
    _send_matrix_via_adapter,
    _send_signal,
    _send_telegram,
    _send_to_platform,
    send_message_tool,
)
# Discord helpers moved to the plugin in #24325.  Import from the new path
# and provide a thin ``_send_discord(token, ...)`` shim that mirrors the
# pre-migration signature so the existing test bodies keep working.
from plugins.platforms.discord.adapter import (
    _DISCORD_STANDALONE_ERROR_BODY_LIMIT_BYTES,
    _DISCORD_STANDALONE_JSON_BODY_LIMIT_BYTES,
    _derive_forum_thread_name,
    _probe_is_forum_cached,
    _remember_channel_is_forum,
    _standalone_send,
)


async def _send_discord(
    token,
    chat_id,
    message,
    *,
    thread_id=None,
    media_files=None,
):
    """Pre-migration ``(token, chat_id, message, …)`` adapter around the
    plugin's ``_standalone_send(pconfig, …)``.  Lets test bodies continue
    to call ``_send_discord("tok", ...)`` without rewriting every signature.
    """
    pconfig = SimpleNamespace(token=token, extra={})
    return await _standalone_send(
        pconfig,
        chat_id,
        message,
        thread_id=thread_id,
        media_files=media_files,
    )


class _StreamingAiohttpContent:
    def __init__(self, body: bytes):
        self._body = body
        self.read_sizes = []

    async def read(self, size=-1):
        self.read_sizes.append(size)
        if not self._body:
            return b""
        if size is None or size < 0:
            chunk = self._body
            self._body = b""
            return chunk
        chunk = self._body[:size]
        self._body = self._body[size:]
        return chunk


class _StreamingAiohttpResponse:
    def __init__(self, status: int, body: bytes):
        self.status = status
        self.content = _StreamingAiohttpContent(body)
        self.closed = False
        self.json = AsyncMock(side_effect=AssertionError("resp.json() should not be used"))
        self.text = AsyncMock(side_effect=AssertionError("resp.text() should not be used"))

    async def __aenter__(self):
        return self

    async def __aexit__(self, *_args):
        return None

    def close(self):
        self.closed = True


class _StreamingAiohttpSession:
    def __init__(self, response: _StreamingAiohttpResponse):
        self.response = response
        self.post = MagicMock(return_value=response)

    async def __aenter__(self):
        return self

    async def __aexit__(self, *_args):
        return None


def _discord_entry():
    """Return the live Discord PlatformEntry, importing lazily so plugin
    discovery is forced exactly once and patches survive across tests."""
    from hermes_cli.plugins import discover_plugins
    from gateway.platform_registry import platform_registry
    discover_plugins()
    return platform_registry.get("discord")


class _patch_discord_sender:
    """Patch the Discord registry entry's ``standalone_sender_fn`` with the
    given mock and translate the production ``(pconfig, ...)`` call shape
    back to the pre-migration ``(token, ...)`` shape the test mocks expect.

    Use as a context manager:

        send_mock = AsyncMock(return_value={...})
        with _patch_discord_sender(send_mock):
            asyncio.run(_send_to_platform(Platform.DISCORD, ...))
        send_mock.assert_awaited_once_with("tok", "chat", "msg",
                                           thread_id=None, media_files=[])
    """

    def __init__(self, mock):
        self._mock = mock
        self._entry = None
        self._original = None

    async def _adapter(self, pconfig, chat_id, message, *, thread_id=None, media_files=None, caption=None):
        token = getattr(pconfig, "token", None)
        # Only forward caption= when set, so mocks written against the
        # pre-caption signature (no caption kwarg) keep working.
        extra = {"caption": caption} if caption is not None else {}
        return await self._mock(
            token, chat_id, message,
            thread_id=thread_id, media_files=media_files, **extra,
        )

    def __enter__(self):
        self._entry = _discord_entry()
        self._original = self._entry.standalone_sender_fn
        self._entry.standalone_sender_fn = self._adapter
        return self._mock

    def __exit__(self, exc_type, exc, tb):
        if self._entry is not None:
            self._entry.standalone_sender_fn = self._original
        return False


def _slack_entry():
    """Return the live Slack PlatformEntry, importing lazily so plugin
    discovery is forced exactly once and patches survive across tests."""
    from hermes_cli.plugins import discover_plugins
    from gateway.platform_registry import platform_registry
    discover_plugins()
    return platform_registry.get("slack")


def _make_recording_slack_sender():
    """Return a plain AsyncMock used to record the formatted Slack text.

    Paired with ``_patch_slack_standalone_sender``, which wraps it so the
    production ``(pconfig, chat_id, raw_text, thread_id=...)`` call is
    translated into the pre-migration ``(token, chat_id, formatted_text,
    thread_ts=...)`` shape — applying ``SlackAdapter.format_message`` exactly
    as the real plugin ``_standalone_send`` does. Tests can then assert on
    ``send.await_args.args[2]`` (the formatted mrkdwn) as before.
    """
    return AsyncMock(return_value={"success": True, "platform": "slack", "message_id": "1"})


class _patch_slack_standalone_sender:
    """Patch the Slack registry entry's ``standalone_sender_fn`` with a wrapper
    that replicates the plugin's mrkdwn formatting then delegates to the given
    mock in the pre-migration call shape. Mirrors ``_patch_discord_sender``.

    Slack mrkdwn formatting moved INTO the plugin's ``_standalone_send`` when
    the adapter migrated (#41112) — previously ``_send_to_platform`` formatted
    the message before calling the old ``_send_slack`` helper. This wrapper
    keeps the "markdown → Slack mrkdwn reaches the wire" behavior tests valid.
    """

    def __init__(self, mock):
        self._mock = mock
        self._entry = None
        self._original = None

    async def _adapter(self, pconfig, chat_id, message, *, thread_id=None, **_kw):
        from plugins.platforms.slack.adapter import SlackAdapter
        formatted = message
        if message:
            try:
                formatted = SlackAdapter.__new__(SlackAdapter).format_message(message)
            except Exception:
                pass
        token = getattr(pconfig, "token", None)
        return await self._mock(token, chat_id, formatted, thread_ts=thread_id)

    def __enter__(self):
        self._entry = _slack_entry()
        self._original = self._entry.standalone_sender_fn
        self._entry.standalone_sender_fn = self._adapter
        return self._mock

    def __exit__(self, exc_type, exc, tb):
        if self._entry is not None:
            self._entry.standalone_sender_fn = self._original
        return False


def _run_async_immediately(coro):
    return asyncio.run(coro)


def _make_config():
    telegram_cfg = SimpleNamespace(enabled=True, token="***", extra={})
    return SimpleNamespace(
        platforms={Platform.TELEGRAM: telegram_cfg},
        get_home_channel=lambda _platform: None,
    ), telegram_cfg


def _install_telegram_mock(monkeypatch, bot):
    parse_mode = SimpleNamespace(MARKDOWN_V2="MarkdownV2", HTML="HTML")
    constants_mod = SimpleNamespace(ParseMode=parse_mode)
    # MessageEntity needed by #27865 mention-detection path; tests don't
    # inspect it but the import must succeed.
    _MessageEntity = lambda **_kw: SimpleNamespace(**_kw)
    telegram_mod = SimpleNamespace(Bot=lambda token: bot, MessageEntity=_MessageEntity, constants=constants_mod)
    monkeypatch.setitem(sys.modules, "telegram", telegram_mod)
    monkeypatch.setitem(sys.modules, "telegram.constants", constants_mod)


def _ensure_slack_mock(monkeypatch):
    if "slack_bolt" in sys.modules and hasattr(sys.modules["slack_bolt"], "__file__"):
        return

    slack_bolt = MagicMock()
    slack_bolt.async_app.AsyncApp = MagicMock
    slack_bolt.adapter.socket_mode.async_handler.AsyncSocketModeHandler = MagicMock

    slack_sdk = MagicMock()
    slack_sdk.web.async_client.AsyncWebClient = MagicMock

    for name, mod in [
        ("slack_bolt", slack_bolt),
        ("slack_bolt.async_app", slack_bolt.async_app),
        ("slack_bolt.adapter", slack_bolt.adapter),
        ("slack_bolt.adapter.socket_mode", slack_bolt.adapter.socket_mode),
        ("slack_bolt.adapter.socket_mode.async_handler", slack_bolt.adapter.socket_mode.async_handler),
        ("slack_sdk", slack_sdk),
        ("slack_sdk.web", slack_sdk.web),
        ("slack_sdk.web.async_client", slack_sdk.web.async_client),
    ]:
        monkeypatch.setitem(sys.modules, name, mod)


class TestSendMessageTool:
    def test_ntfy_topic_target_is_explicit(self):
        chat_id, thread_id, is_explicit = _parse_target_ref("ntfy", "alerts-channel")

        assert chat_id == "alerts-channel"
        assert thread_id is None
        assert is_explicit is True

    def test_ntfy_topic_target_bypasses_channel_directory(self):
        ntfy_platform = Platform("ntfy")
        ntfy_cfg = SimpleNamespace(enabled=True, token=None, extra={"topic": "hermes-in"})
        config = SimpleNamespace(
            platforms={ntfy_platform: ntfy_cfg},
            get_home_channel=lambda _platform: None,
        )

        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch("gateway.channel_directory.resolve_channel_name", side_effect=AssertionError("should not resolve ntfy topics")), \
             patch("model_tools._run_async", side_effect=_run_async_immediately), \
             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})) as send_mock, \
             patch("gateway.mirror.mirror_to_session", return_value=True):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "ntfy:alerts-channel",
                        "message": "done",
                    }
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once_with(
            ntfy_platform,
            ntfy_cfg,
            "alerts-channel",
            "done",
            thread_id=None,
            media_files=[],
            force_document=False,
        )

    def test_cron_duplicate_target_is_skipped_and_explained(self):
        home = SimpleNamespace(chat_id="-1001")
        config, _telegram_cfg = _make_config()
        config.get_home_channel = lambda _platform: home

        with patch.dict(
            os.environ,
            {
                "HERMES_CRON_AUTO_DELIVER_PLATFORM": "telegram",
                "HERMES_CRON_AUTO_DELIVER_CHAT_ID": "-1001",
            },
            clear=False,
        ), \
             patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch("model_tools._run_async", side_effect=_run_async_immediately), \
             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})) as send_mock, \
             patch("gateway.mirror.mirror_to_session", return_value=True) as mirror_mock:
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "telegram",
                        "message": "hello",
                    }
                )
            )

        assert result["success"] is True
        assert result["skipped"] is True
        assert result["reason"] == "cron_auto_delivery_duplicate_target"
        assert "final response" in result["note"]
        send_mock.assert_not_awaited()
        mirror_mock.assert_not_called()

    def test_resolved_telegram_topic_name_preserves_thread_id(self):
        config, telegram_cfg = _make_config()

        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch("gateway.channel_directory.resolve_channel_name", return_value="-1001:17585"), \
             patch("model_tools._run_async", side_effect=_run_async_immediately), \
             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})) as send_mock, \
             patch("gateway.mirror.mirror_to_session", return_value=True):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "telegram:Coaching Chat / topic 17585",
                        "message": "hello",
                    }
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once_with(
            Platform.TELEGRAM,
            telegram_cfg,
            "-1001",
            "hello",
            thread_id="17585",
            media_files=[],
            force_document=False,
        )

    def test_display_label_target_resolves_via_channel_directory(self, tmp_path):
        config, telegram_cfg = _make_config()
        cache_file = tmp_path / "channel_directory.json"
        cache_file.write_text(json.dumps({
            "updated_at": "2026-01-01T00:00:00",
            "platforms": {
                "telegram": [
                    {"id": "-1001:17585", "name": "Coaching Chat / topic 17585", "type": "group"}
                ]
            },
        }))

        with patch("gateway.channel_directory.DIRECTORY_PATH", cache_file), \
             patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch("model_tools._run_async", side_effect=_run_async_immediately), \
             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})) as send_mock, \
             patch("gateway.mirror.mirror_to_session", return_value=True):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "telegram:Coaching Chat / topic 17585 (group)",
                        "message": "hello",
                    }
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once_with(
            Platform.TELEGRAM,
            telegram_cfg,
            "-1001",
            "hello",
            thread_id="17585",
            media_files=[],
            force_document=False,
        )

    def test_resolved_slack_thread_name_preserves_thread_id(self):
        slack_cfg = SimpleNamespace(enabled=True, token="xoxb-test", extra={})
        config = SimpleNamespace(
            platforms={Platform.SLACK: slack_cfg},
            get_home_channel=lambda _platform: None,
        )

        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch("gateway.channel_directory.resolve_channel_name", return_value="C123ABCDEF:171.000001"), \
             patch("model_tools._run_async", side_effect=_run_async_immediately), \
             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})) as send_mock, \
             patch("gateway.mirror.mirror_to_session", return_value=True):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "slack:ops / topic 171.000001",
                        "message": "hello",
                    }
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once_with(
            Platform.SLACK,
            slack_cfg,
            "C123ABCDEF",
            "hello",
            thread_id="171.000001",
            media_files=[],
            force_document=False,
        )

    def test_resolved_matrix_thread_name_preserves_thread_id(self):
        matrix_cfg = SimpleNamespace(
            enabled=True,
            token="tok",
            extra={"homeserver": "https://matrix.example.com"},
        )
        config = SimpleNamespace(
            platforms={Platform.MATRIX: matrix_cfg},
            get_home_channel=lambda _platform: None,
        )

        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch(
                 "gateway.channel_directory.resolve_channel_name",
                 return_value="!roomid:matrix.example.org:$thread123:matrix.example.org",
             ), \
             patch("model_tools._run_async", side_effect=_run_async_immediately), \
             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})) as send_mock, \
             patch("gateway.mirror.mirror_to_session", return_value=True):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "matrix:Ops / topic $thread123",
                        "message": "hello",
                    }
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once_with(
            Platform.MATRIX,
            matrix_cfg,
            "!roomid:matrix.example.org",
            "hello",
            thread_id="$thread123:matrix.example.org",
            media_files=[],
            force_document=False,
        )

    def test_mirror_receives_current_session_user_id(self):
        config, _telegram_cfg = _make_config()

        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch("model_tools._run_async", side_effect=_run_async_immediately), \
             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})), \
             patch("gateway.session_context.get_session_env") as get_session_env_mock, \
             patch("gateway.mirror.mirror_to_session", return_value=True) as mirror_mock:
            get_session_env_mock.side_effect = lambda name, default="": {
                "HERMES_SESSION_PLATFORM": "telegram",
                "HERMES_SESSION_USER_ID": "user-123",
            }.get(name, default)
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "telegram:12345",
                        "message": "hello",
                    }
                )
            )

        assert result["success"] is True
        mirror_mock.assert_called_once_with(
            "telegram",
            "12345",
            "hello",
            source_label="telegram",
            thread_id=None,
            user_id="user-123",
        )

    def test_media_tag_outside_allowed_roots_is_not_sent(self, tmp_path, monkeypatch):
        # This test exercises the strict-allowlist path; force strict mode on
        # and disable recency trust so the freshly-written tmp_path file is
        # not auto-accepted by the trust window. (Recency trust is covered
        # in test_platform_base.py. The public default flipped to non-strict
        # in 2026-05; this test pins strict on explicitly.)
        monkeypatch.setenv("HERMES_MEDIA_DELIVERY_STRICT", "1")
        monkeypatch.setenv("HERMES_MEDIA_TRUST_RECENT_FILES", "0")
        config, telegram_cfg = _make_config()
        secret = tmp_path / "secret.pdf"
        secret.write_bytes(b"%PDF secret")

        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch("model_tools._run_async", side_effect=_run_async_immediately), \
             patch("tools.send_message_tool._send_to_platform", new=AsyncMock(return_value={"success": True})) as send_mock, \
             patch("gateway.mirror.mirror_to_session", return_value=True):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "telegram:12345",
                        "message": f"hello\nMEDIA:{secret}",
                    }
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once_with(
            Platform.TELEGRAM,
            telegram_cfg,
            "12345",
            "hello",
            thread_id=None,
            media_files=[],
            force_document=False,
        )

    def test_top_level_send_failure_redacts_query_token(self):
        config, _telegram_cfg = _make_config()
        leaked = "very-secret-query-token-123456"

        def _raise_and_close(coro):
            coro.close()
            raise RuntimeError(
                f"transport error: https://api.example.com/send?access_token={leaked}"
            )

        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False), \
             patch("model_tools._run_async", side_effect=_raise_and_close):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "telegram:-1001",
                        "message": "hello",
                    }
                )
            )

        assert "error" in result
        assert leaked not in result["error"]
        assert "access_token=***" in result["error"]


class TestSendTelegramMediaDelivery:
    def test_sends_photo_with_caption_for_media_tag(self, tmp_path, monkeypatch):
        # A single captionable image + short text now rides as the photo's
        # native caption (MEDIA:<path> caption), not a separate text message.
        image_path = tmp_path / "photo.png"
        image_path.write_bytes(b"\x89PNG\r\n\x1a\n" + b"\x00" * 32)

        bot = MagicMock()
        bot.send_message = AsyncMock(return_value=SimpleNamespace(message_id=1))
        bot.send_photo = AsyncMock(return_value=SimpleNamespace(message_id=2))
        bot.send_video = AsyncMock()
        bot.send_voice = AsyncMock()
        bot.send_audio = AsyncMock()
        bot.send_document = AsyncMock()
        _install_telegram_mock(monkeypatch, bot)

        result = asyncio.run(
            _send_telegram(
                "token",
                "12345",
                "Hello there",
                media_files=[(str(image_path), False)],
            )
        )

        assert result["success"] is True
        assert result["message_id"] == "2"
        # No separate text send — the caption rides the photo bubble.
        bot.send_message.assert_not_awaited()
        bot.send_photo.assert_awaited_once()
        assert bot.send_photo.await_args.kwargs.get("caption") == "Hello there"

    def test_sends_voice_for_ogg_with_voice_directive(self, tmp_path, monkeypatch):
        voice_path = tmp_path / "voice.ogg"
        voice_path.write_bytes(b"OggS" + b"\x00" * 32)

        bot = MagicMock()
        bot.send_message = AsyncMock()
        bot.send_photo = AsyncMock()
        bot.send_video = AsyncMock()
        bot.send_voice = AsyncMock(return_value=SimpleNamespace(message_id=7))
        bot.send_audio = AsyncMock()
        bot.send_document = AsyncMock()
        _install_telegram_mock(monkeypatch, bot)

        result = asyncio.run(
            _send_telegram(
                "token",
                "12345",
                "",
                media_files=[(str(voice_path), True)],
            )
        )

        assert result["success"] is True
        bot.send_voice.assert_awaited_once()
        bot.send_audio.assert_not_awaited()
        bot.send_message.assert_not_awaited()

    def test_sends_audio_for_mp3(self, tmp_path, monkeypatch):
        audio_path = tmp_path / "clip.mp3"
        audio_path.write_bytes(b"ID3" + b"\x00" * 32)

        bot = MagicMock()
        bot.send_message = AsyncMock()
        bot.send_photo = AsyncMock()
        bot.send_video = AsyncMock()
        bot.send_voice = AsyncMock()
        bot.send_audio = AsyncMock(return_value=SimpleNamespace(message_id=8))
        bot.send_document = AsyncMock()
        _install_telegram_mock(monkeypatch, bot)

        result = asyncio.run(
            _send_telegram(
                "token",
                "12345",
                "",
                media_files=[(str(audio_path), False)],
            )
        )

        assert result["success"] is True
        bot.send_audio.assert_awaited_once()
        bot.send_voice.assert_not_awaited()

    def test_missing_media_returns_error_without_leaking_raw_tag(self, monkeypatch):
        bot = MagicMock()
        bot.send_message = AsyncMock()
        bot.send_photo = AsyncMock()
        bot.send_video = AsyncMock()
        bot.send_voice = AsyncMock()
        bot.send_audio = AsyncMock()
        bot.send_document = AsyncMock()
        _install_telegram_mock(monkeypatch, bot)

        result = asyncio.run(
            _send_telegram(
                "token",
                "12345",
                "",
                media_files=[("/tmp/does-not-exist.png", False)],
            )
        )

        assert "error" in result
        assert "No deliverable text or media remained" in result["error"]
        bot.send_message.assert_not_awaited()


# ---------------------------------------------------------------------------
# Regression: long messages are chunked before platform dispatch
# ---------------------------------------------------------------------------


class TestSendToPlatformChunking:
    def test_long_message_is_chunked(self):
        """Messages exceeding the platform limit are split into multiple sends."""
        send = AsyncMock(return_value={"success": True, "message_id": "1"})
        long_msg = "word " * 1000  # ~5000 chars, well over Discord's 2000 limit
        with _patch_discord_sender(send):
            result = asyncio.run(
                _send_to_platform(
                    Platform.DISCORD,
                    SimpleNamespace(enabled=True, token="***", extra={}),
                    "ch", long_msg,
                )
            )
        assert result["success"] is True
        assert send.await_count >= 3
        for call in send.await_args_list:
            assert len(call.args[2]) <= 2020  # each chunk fits the limit

    def test_slack_messages_are_formatted_before_send(self, monkeypatch):
        _ensure_slack_mock(monkeypatch)

        import plugins.platforms.slack.adapter as slack_mod

        monkeypatch.setattr(slack_mod, "SLACK_AVAILABLE", True)
        send = _make_recording_slack_sender()

        with _patch_slack_standalone_sender(send):
            result = asyncio.run(
                _send_to_platform(
                    Platform.SLACK,
                    SimpleNamespace(enabled=True, token="***", extra={}),
                    "C123",
                    "**hello** from [Hermes](<https://example.com>)",
                )
            )

        assert result["success"] is True
        send.assert_awaited_once_with(
            "***",
            "C123",
            "*hello* from <https://example.com|Hermes>",
            thread_ts=None,
        )

    def test_slack_bold_italic_formatted_before_send(self, monkeypatch):
        """Bold+italic ***text*** survives tool-layer formatting."""
        _ensure_slack_mock(monkeypatch)
        import plugins.platforms.slack.adapter as slack_mod

        monkeypatch.setattr(slack_mod, "SLACK_AVAILABLE", True)
        send = _make_recording_slack_sender()
        with _patch_slack_standalone_sender(send):
            result = asyncio.run(
                _send_to_platform(
                    Platform.SLACK,
                    SimpleNamespace(enabled=True, token="***", extra={}),
                    "C123",
                    "***important*** update",
                )
            )
        assert result["success"] is True
        sent_text = send.await_args.args[2]
        assert "*_important_*" in sent_text

    def test_slack_blockquote_formatted_before_send(self, monkeypatch):
        """Blockquote '>' markers must survive formatting (not escaped to '&gt;')."""
        _ensure_slack_mock(monkeypatch)
        import plugins.platforms.slack.adapter as slack_mod

        monkeypatch.setattr(slack_mod, "SLACK_AVAILABLE", True)
        send = _make_recording_slack_sender()
        with _patch_slack_standalone_sender(send):
            result = asyncio.run(
                _send_to_platform(
                    Platform.SLACK,
                    SimpleNamespace(enabled=True, token="***", extra={}),
                    "C123",
                    "> important quote\n\nnormal text & stuff",
                )
            )
        assert result["success"] is True
        sent_text = send.await_args.args[2]
        assert sent_text.startswith("> important quote")
        assert "&amp;" in sent_text  # & is escaped
        assert "&gt;" not in sent_text.split("\n")[0]  # > in blockquote is NOT escaped

    def test_slack_pre_escaped_entities_not_double_escaped(self, monkeypatch):
        """Pre-escaped HTML entities survive tool-layer formatting without double-escaping."""
        _ensure_slack_mock(monkeypatch)
        import plugins.platforms.slack.adapter as slack_mod
        monkeypatch.setattr(slack_mod, "SLACK_AVAILABLE", True)
        send = _make_recording_slack_sender()
        with _patch_slack_standalone_sender(send):
            result = asyncio.run(
                _send_to_platform(
                    Platform.SLACK,
                    SimpleNamespace(enabled=True, token="***", extra={}),
                    "C123",
                    "AT&amp;T &lt;tag&gt; test",
                )
            )
        assert result["success"] is True
        sent_text = send.await_args.args[2]
        assert "&amp;amp;" not in sent_text
        assert "&amp;lt;" not in sent_text
        assert "AT&amp;T" in sent_text

    def test_slack_url_with_parens_formatted_before_send(self, monkeypatch):
        """Wikipedia-style URL with parens survives tool-layer formatting."""
        _ensure_slack_mock(monkeypatch)
        import plugins.platforms.slack.adapter as slack_mod
        monkeypatch.setattr(slack_mod, "SLACK_AVAILABLE", True)
        send = _make_recording_slack_sender()
        with _patch_slack_standalone_sender(send):
            result = asyncio.run(
                _send_to_platform(
                    Platform.SLACK,
                    SimpleNamespace(enabled=True, token="***", extra={}),
                    "C123",
                    "See [Foo](https://en.wikipedia.org/wiki/Foo_(bar))",
                )
            )
        assert result["success"] is True
        sent_text = send.await_args.args[2]
        assert "<https://en.wikipedia.org/wiki/Foo_(bar)|Foo>" in sent_text

    def test_telegram_markdown_expansion_is_chunked_before_send(self, monkeypatch):
        """Telegram chunking must account for MarkdownV2 escaping expansion.

        A raw message under 4096 UTF-16 units can inflate past the limit once
        MarkdownV2-escaped (each `!`/`.`/`-` becomes `\\!`/`\\.`/`\\-`). The
        send path must chunk the *formatted* text so no single send exceeds
        4096 (issue #28557).
        """
        from gateway.platforms.base import utf16_len

        send_lengths = []

        async def fake_send_message(**kwargs):
            text = kwargs["text"]
            send_lengths.append(utf16_len(text))
            if utf16_len(text) > 4096:
                raise Exception("Message is too long")
            return SimpleNamespace(message_id=len(send_lengths))

        bot = MagicMock()
        bot.send_message = AsyncMock(side_effect=fake_send_message)
        bot.send_photo = AsyncMock()
        bot.send_video = AsyncMock()
        bot.send_voice = AsyncMock()
        bot.send_audio = AsyncMock()
        bot.send_document = AsyncMock()
        _install_telegram_mock(monkeypatch, bot)

        result = asyncio.run(
            _send_to_platform(
                Platform.TELEGRAM,
                SimpleNamespace(enabled=True, token="tok", extra={}),
                "123",
                "!" * 4096,  # raw 4096 -> ~8192 after MarkdownV2 escaping
            )
        )

        assert result["success"] is True
        assert bot.send_message.await_count >= 2
        assert max(send_lengths) <= 4096

    def test_telegram_media_attaches_after_long_text_chunks(self, tmp_path, monkeypatch):
        """Long text is split into multiple chunks, then media is attached."""
        image_path = tmp_path / "photo.png"
        image_path.write_bytes(b"\x89PNG\r\n\x1a\n" + b"\x00" * 32)

        bot = MagicMock()
        bot.send_message = AsyncMock(return_value=SimpleNamespace(message_id=1))
        bot.send_photo = AsyncMock(return_value=SimpleNamespace(message_id=2))
        bot.send_video = AsyncMock()
        bot.send_voice = AsyncMock()
        bot.send_audio = AsyncMock()
        bot.send_document = AsyncMock()
        _install_telegram_mock(monkeypatch, bot)

        long_msg = "word " * 2000  # ~10000 chars, well over Telegram's 4096 limit
        result = asyncio.run(
            _send_to_platform(
                Platform.TELEGRAM,
                SimpleNamespace(enabled=True, token="tok", extra={}),
                "123",
                long_msg,
                media_files=[(str(image_path), False)],
            )
        )

        assert result["success"] is True
        assert bot.send_message.await_count >= 3
        bot.send_photo.assert_awaited_once()

    def test_matrix_media_uses_native_adapter_helper(self, tmp_path):
        doc_path = tmp_path / "test-send-message-matrix.pdf"
        doc_path.write_bytes(b"%PDF-1.4 test")

        try:
            helper = AsyncMock(return_value={"success": True, "platform": "matrix", "chat_id": "!room:example.com", "message_id": "$evt"})
            with patch("tools.send_message_tool._send_matrix_via_adapter", helper):
                result = asyncio.run(
                    _send_to_platform(
                        Platform.MATRIX,
                        SimpleNamespace(enabled=True, token="tok", extra={"homeserver": "https://matrix.example.com"}),
                        "!room:example.com",
                        "here you go",
                        media_files=[(str(doc_path), False)],
                    )
                )

            assert result["success"] is True
            helper.assert_awaited_once()
            call = helper.await_args
            assert call.args[1] == "!room:example.com"
            assert call.args[2] == "here you go"
            assert call.kwargs["media_files"] == [(str(doc_path), False)]
        finally:
            doc_path.unlink(missing_ok=True)

    def test_matrix_text_only_uses_adapter_path(self):
        """Text-only Matrix sends must go through the E2EE-capable adapter.

        The raw-HTTP standalone path (registry standalone_sender_fn) sends
        cleartext, so in an E2EE room text-only messages arrived with a red
        padlock. All Matrix sends now route through _send_matrix_via_adapter,
        which encrypts via the mautrix adapter (live gateway session when
        available, encryption-aware ephemeral adapter otherwise)."""
        from hermes_cli.plugins import discover_plugins
        from gateway.platform_registry import platform_registry
        discover_plugins()
        helper = AsyncMock(return_value={"success": True, "platform": "matrix", "chat_id": "!room:ex.com", "message_id": "$txt"})
        standalone = AsyncMock()
        matrix_entry = platform_registry.get("matrix")
        original_sender = matrix_entry.standalone_sender_fn
        matrix_entry.standalone_sender_fn = standalone
        try:
            with patch("tools.send_message_tool._send_matrix_via_adapter", helper):
                result = asyncio.run(
                    _send_to_platform(
                        Platform.MATRIX,
                        SimpleNamespace(enabled=True, token="tok", extra={"homeserver": "https://matrix.example.com"}),
                        "!room:ex.com",
                        "just text, no files",
                    )
                )
        finally:
            matrix_entry.standalone_sender_fn = original_sender

        assert result["success"] is True
        helper.assert_awaited_once()
        standalone.assert_not_awaited()

    def test_send_matrix_via_adapter_sends_document(self, tmp_path):
        file_path = tmp_path / "report.pdf"
        file_path.write_bytes(b"%PDF-1.4 test")

        calls = []

        class FakeAdapter:
            def __init__(self, _config):
                self.connected = False

            async def connect(self, *, is_reconnect: bool = False):
                self.connected = True
                calls.append(("connect",))
                return True

            async def send(self, chat_id, message, metadata=None):
                calls.append(("send", chat_id, message, metadata))
                return SimpleNamespace(success=True, message_id="$text")

            async def send_document(self, chat_id, file_path, metadata=None):
                calls.append(("send_document", chat_id, file_path, metadata))
                return SimpleNamespace(success=True, message_id="$file")

            async def disconnect(self):
                calls.append(("disconnect",))

        fake_module = SimpleNamespace(MatrixAdapter=FakeAdapter)

        with patch.dict(sys.modules, {"plugins.platforms.matrix.adapter": fake_module}):
            result = asyncio.run(
                _send_matrix_via_adapter(
                    SimpleNamespace(enabled=True, token="tok", extra={"homeserver": "https://matrix.example.com"}),
                    "!room:example.com",
                    "report attached",
                    media_files=[(str(file_path), False)],
                )
            )

        assert result == {
            "success": True,
            "platform": "matrix",
            "chat_id": "!room:example.com",
            "message_id": "$file",
        }
        assert calls == [
            ("connect",),
            ("send", "!room:example.com", "report attached", None),
            ("send_document", "!room:example.com", str(file_path), None),
            ("disconnect",),
        ]


class TestMatrixMediaLiveAdapterReuse:
    """Verify _send_matrix_via_adapter reuses the live gateway adapter
    when available, avoiding per-message E2EE re-init storms (#46310)."""

    def test_live_adapter_skips_connect_disconnect(self, tmp_path):
        """When a live gateway adapter exists, no connect() or disconnect()
        should be called — the persistent E2EE session is reused."""
        img_path = tmp_path / "photo.png"
        img_path.write_bytes(b"\x89PNG\r\n")

        calls = []

        class LiveAdapter:
            async def send(self, chat_id, message, metadata=None):
                calls.append(("send", chat_id, message))
                return SimpleNamespace(success=True, message_id="$text")

            async def send_image_file(self, chat_id, path, metadata=None):
                calls.append(("send_image_file", chat_id, path))
                return SimpleNamespace(success=True, message_id="$img")

        live_adapter = LiveAdapter()
        fake_runner = SimpleNamespace(
            adapters={Platform.MATRIX: live_adapter}
        )

        with patch(
            "gateway.run._gateway_runner_ref",
            return_value=fake_runner,
        ), patch.dict(
            sys.modules, {"plugins.platforms.matrix.adapter": SimpleNamespace()}
        ):
            result = asyncio.run(
                _send_matrix_via_adapter(
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "!room:example.com",
                    "here is an image",
                    media_files=[(str(img_path), False)],
                )
            )

        assert result["success"] is True
        assert result["message_id"] == "$img"
        # Only send + send_image_file; no connect / disconnect
        assert calls == [
            ("send", "!room:example.com", "here is an image"),
            ("send_image_file", "!room:example.com", str(img_path)),
        ]

    def test_live_adapter_not_available_falls_back_to_ephemeral(self, tmp_path):
        """When _gateway_runner_ref returns None, the ephemeral adapter
        path (connect + disconnect) is used as before."""
        doc_path = tmp_path / "doc.pdf"
        doc_path.write_bytes(b"%PDF-1.4")

        calls = []

        class EphemeralAdapter:
            def __init__(self, _config):
                pass

            async def connect(self):
                calls.append(("connect",))
                return True

            async def send(self, chat_id, message, metadata=None):
                calls.append(("send", chat_id, message))
                return SimpleNamespace(success=True, message_id="$txt")

            async def send_document(self, chat_id, path, metadata=None):
                calls.append(("send_document", chat_id, path))
                return SimpleNamespace(success=True, message_id="$doc")

            async def disconnect(self):
                calls.append(("disconnect",))

        fake_module = SimpleNamespace(MatrixAdapter=EphemeralAdapter)

        with patch(
            "gateway.run._gateway_runner_ref", return_value=None
        ), patch.dict(sys.modules, {"plugins.platforms.matrix.adapter": fake_module}):
            result = asyncio.run(
                _send_matrix_via_adapter(
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "!room:example.com",
                    "report attached",
                    media_files=[(str(doc_path), False)],
                )
            )

        assert result["success"] is True
        assert calls == [
            ("connect",),
            ("send", "!room:example.com", "report attached"),
            ("send_document", "!room:example.com", str(doc_path)),
            ("disconnect",),
        ]

    def test_live_adapter_no_matrix_adapter_falls_back(self):
        """When the runner exists but has no Matrix adapter registered,
        fall back to ephemeral."""
        calls = []

        class EphemeralAdapter:
            def __init__(self, _config):
                pass

            async def connect(self):
                calls.append(("connect",))
                return True

            async def send(self, chat_id, message, metadata=None):
                calls.append(("send",))
                return SimpleNamespace(success=True, message_id="$txt")

            async def disconnect(self):
                calls.append(("disconnect",))

        # Runner exists but adapters dict has no MATRIX key
        fake_runner = SimpleNamespace(adapters={})
        fake_module = SimpleNamespace(MatrixAdapter=EphemeralAdapter)

        with patch(
            "gateway.run._gateway_runner_ref",
            return_value=fake_runner,
        ), patch.dict(sys.modules, {"plugins.platforms.matrix.adapter": fake_module}):
            result = asyncio.run(
                _send_matrix_via_adapter(
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "!room:example.com",
                    "hello",
                )
            )

        assert result["success"] is True
        assert ("connect",) in calls
        assert ("disconnect",) in calls


# ---------------------------------------------------------------------------
# HTML auto-detection in Telegram send
# ---------------------------------------------------------------------------


class TestSendToPlatformWhatsapp:
    def test_whatsapp_routes_via_local_bridge_sender(self):
        """WhatsApp delivery routes through the plugin's registry
        standalone_sender_fn (was tools.send_message_tool._send_whatsapp
        before the #41112 plugin migration)."""
        from hermes_cli.plugins import discover_plugins
        from gateway.platform_registry import platform_registry
        discover_plugins()
        chat_id = "test-user@lid"
        async_mock = AsyncMock(return_value={"success": True, "platform": "whatsapp", "chat_id": chat_id, "message_id": "abc123"})

        wa_entry = platform_registry.get("whatsapp")
        original_sender = wa_entry.standalone_sender_fn
        wa_entry.standalone_sender_fn = async_mock
        try:
            result = asyncio.run(
                _send_to_platform(
                    Platform.WHATSAPP,
                    SimpleNamespace(enabled=True, token=None, extra={"bridge_port": 3000}),
                    chat_id,
                    "hello from hermes",
                )
            )
        finally:
            wa_entry.standalone_sender_fn = original_sender

        assert result["success"] is True
        # _registry_standalone_send passes (pconfig, chat_id, message, thread_id=None)
        async_mock.assert_awaited_once()
        _call = async_mock.await_args
        assert _call.args[1] == chat_id
        assert _call.args[2] == "hello from hermes"


class TestSendTelegramHtmlDetection:
    """Verify that messages containing HTML tags are sent with parse_mode=HTML
    and that plain / markdown messages use MarkdownV2."""

    def _make_bot(self):
        bot = MagicMock()
        bot.send_message = AsyncMock(return_value=SimpleNamespace(message_id=1))
        bot.send_photo = AsyncMock()
        bot.send_video = AsyncMock()
        bot.send_voice = AsyncMock()
        bot.send_audio = AsyncMock()
        bot.send_document = AsyncMock()
        return bot

    def test_html_message_uses_html_parse_mode(self, monkeypatch):
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(
            _send_telegram("tok", "123", "<b>Hello</b> world")
        )

        bot.send_message.assert_awaited_once()
        kwargs = bot.send_message.await_args.kwargs
        assert kwargs["parse_mode"] == "HTML"
        assert kwargs["text"] == "<b>Hello</b> world"

    def test_plain_text_uses_markdown_v2(self, monkeypatch):
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(
            _send_telegram("tok", "123", "Just plain text, no tags")
        )

        bot.send_message.assert_awaited_once()
        kwargs = bot.send_message.await_args.kwargs
        assert kwargs["parse_mode"] == "MarkdownV2"

    def test_disable_link_previews_sets_disable_web_page_preview(self, monkeypatch):
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(
            _send_telegram("tok", "123", "https://example.com", disable_link_previews=True)
        )

        kwargs = bot.send_message.await_args.kwargs
        assert kwargs["disable_web_page_preview"] is True

    def test_html_with_code_and_pre_tags(self, monkeypatch):
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        html = "<pre>code block</pre> and <code>inline</code>"
        asyncio.run(_send_telegram("tok", "123", html))

        kwargs = bot.send_message.await_args.kwargs
        assert kwargs["parse_mode"] == "HTML"

    def test_closing_tag_detected(self, monkeypatch):
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(_send_telegram("tok", "123", "text </div> more"))

        kwargs = bot.send_message.await_args.kwargs
        assert kwargs["parse_mode"] == "HTML"

    def test_angle_brackets_in_math_not_detected(self, monkeypatch):
        """Expressions like 'x < 5' or '3 > 2' should not trigger HTML mode."""
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(_send_telegram("tok", "123", "if x < 5 then y > 2"))

        kwargs = bot.send_message.await_args.kwargs
        assert kwargs["parse_mode"] == "MarkdownV2"

    def test_html_parse_failure_falls_back_to_plain(self, monkeypatch):
        """If Telegram rejects the HTML, fall back to plain text."""
        bot = self._make_bot()
        bot.send_message = AsyncMock(
            side_effect=[
                Exception("Bad Request: can't parse entities: unsupported html tag"),
                SimpleNamespace(message_id=2),  # plain fallback succeeds
            ]
        )
        _install_telegram_mock(monkeypatch, bot)

        result = asyncio.run(
            _send_telegram("tok", "123", "<invalid>broken html</invalid>")
        )

        assert result["success"] is True
        assert bot.send_message.await_count == 2
        second_call = bot.send_message.await_args_list[1].kwargs
        assert second_call["parse_mode"] is None

    def test_transient_bad_gateway_retries_text_send(self, monkeypatch):
        bot = self._make_bot()
        bot.send_message = AsyncMock(
            side_effect=[
                Exception("502 Bad Gateway"),
                SimpleNamespace(message_id=2),
            ]
        )
        _install_telegram_mock(monkeypatch, bot)

        with patch("asyncio.sleep", new=AsyncMock()) as sleep_mock:
            result = asyncio.run(_send_telegram("tok", "123", "hello"))

        assert result["success"] is True
        assert bot.send_message.await_count == 2
        sleep_mock.assert_awaited_once()


class TestSendTelegramThreadIdMapping:
    """General-topic mapping in _send_telegram (issue #22267).

    Telegram forum supergroups address the General topic as
    ``message_thread_id="1"`` on incoming updates, but the Bot API rejects
    sends with ``message_thread_id=1`` ("Message thread not found"). The
    gateway adapter's ``_message_thread_id_for_send`` helper maps "1" to
    ``None`` for that reason; the standalone ``_send_telegram`` helper used
    by the ``send_message`` tool needs the same mapping.
    """

    def _make_bot(self):
        bot = MagicMock()
        bot.send_message = AsyncMock(return_value=SimpleNamespace(message_id=1))
        return bot

    def test_general_topic_thread_id_omitted(self, monkeypatch):
        """thread_id="1" must be dropped before calling the Bot API."""
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(_send_telegram("tok", "-1001234567890", "hello", thread_id="1"))

        bot.send_message.assert_awaited_once()
        kwargs = bot.send_message.await_args.kwargs
        assert "message_thread_id" not in kwargs

    def test_non_general_topic_thread_id_preserved(self, monkeypatch):
        """Real forum-topic thread ids (>1) still pass through as ints."""
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(_send_telegram("tok", "-1001234567890", "hello", thread_id="17585"))

        kwargs = bot.send_message.await_args.kwargs
        assert kwargs["message_thread_id"] == 17585

    def test_no_thread_id_no_kwarg(self, monkeypatch):
        """With no thread_id, message_thread_id must not appear in kwargs."""
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(_send_telegram("tok", "-1001234567890", "hello"))

        kwargs = bot.send_message.await_args.kwargs
        assert "message_thread_id" not in kwargs

    def test_general_topic_thread_id_int_input_also_dropped(self, monkeypatch):
        """thread_id passed as the int 1 (not str) must still be dropped."""
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        asyncio.run(_send_telegram("tok", "-1001234567890", "hello", thread_id=1))

        kwargs = bot.send_message.await_args.kwargs
        assert "message_thread_id" not in kwargs

    def test_thread_not_found_retries_without_message_thread_id(self, monkeypatch):
        """When send_message raises "thread not found", retry without thread_id (#27012)."""
        bot = self._make_bot()
        _install_telegram_mock(monkeypatch, bot)

        # First call raises thread-not-found, second succeeds
        bot.send_message = AsyncMock(side_effect=[
            Exception("Bad Request: message thread not found"),
            SimpleNamespace(message_id=2),
        ])

        asyncio.run(
            _send_telegram("tok", "-1001234567890", "hello", thread_id="17585")
        )

        assert bot.send_message.await_count == 2
        # First call: should include message_thread_id=17585
        call1_kwargs = bot.send_message.await_args_list[0].kwargs
        assert call1_kwargs["message_thread_id"] == 17585
        # Second call (retry): should NOT include message_thread_id
        call2_kwargs = bot.send_message.await_args_list[1].kwargs
        assert "message_thread_id" not in call2_kwargs

    def test_thread_not_found_for_media_retries_without_message_thread_id(self, monkeypatch, tmp_path):
        """Media send with stale thread_id retries without it (#27012)."""
        bot = self._make_bot()
        # Mock send_document to fail with thread-not-found, then succeed
        bot.send_document = AsyncMock(side_effect=[
            Exception("Bad Request: message thread not found"),
            SimpleNamespace(message_id=3),
        ])
        _install_telegram_mock(monkeypatch, bot)

        # Create a test file
        test_file = tmp_path / "doc.txt"
        test_file.write_text("test content")

        asyncio.run(
            _send_telegram(
                "tok", "-1001234567890", "",
                media_files=[(str(test_file), False)],
                thread_id="17585",
            )
        )

        assert bot.send_document.await_count == 2
        # First call: should include message_thread_id=17585
        call1_kwargs = bot.send_document.await_args_list[0].kwargs
        assert call1_kwargs["message_thread_id"] == 17585
        # Second call (retry): should NOT include message_thread_id
        call2_kwargs = bot.send_document.await_args_list[1].kwargs
        assert "message_thread_id" not in call2_kwargs


# ---------------------------------------------------------------------------
# Tests for Discord thread_id support
# ---------------------------------------------------------------------------


class TestParseTargetRefDiscord:
    """_parse_target_ref correctly extracts chat_id and thread_id for Discord."""

    def test_discord_chat_id_with_thread_id(self):
        """discord:chat_id:thread_id returns both values."""
        chat_id, thread_id, is_explicit = _parse_target_ref("discord", "-1001234567890:17585")
        assert chat_id == "-1001234567890"
        assert thread_id == "17585"
        assert is_explicit is True

    def test_discord_chat_id_without_thread_id(self):
        """discord:chat_id returns None for thread_id."""
        chat_id, thread_id, is_explicit = _parse_target_ref("discord", "9876543210")
        assert chat_id == "9876543210"
        assert thread_id is None
        assert is_explicit is True

    def test_discord_large_snowflake_without_thread(self):
        """Large Discord snowflake IDs work without thread."""
        chat_id, thread_id, is_explicit = _parse_target_ref("discord", "1003724596514")
        assert chat_id == "1003724596514"
        assert thread_id is None
        assert is_explicit is True

    def test_discord_channel_with_thread(self):
        """Full Discord format: channel:thread."""
        chat_id, thread_id, is_explicit = _parse_target_ref("discord", "1003724596514:99999")
        assert chat_id == "1003724596514"
        assert thread_id == "99999"
        assert is_explicit is True

    def test_discord_whitespace_is_stripped(self):
        """Whitespace around Discord targets is stripped."""
        chat_id, thread_id, is_explicit = _parse_target_ref("discord", "  123456:789  ")
        assert chat_id == "123456"
        assert thread_id == "789"
        assert is_explicit is True


class TestParseTargetRefMatrix:
    """_parse_target_ref correctly handles Matrix room IDs and user MXIDs."""

    def test_matrix_thread_target_is_explicit(self):
        """Session-derived Matrix thread targets round-trip as room + event id."""
        chat_id, thread_id, is_explicit = _parse_target_ref(
            "matrix",
            "!HLOQwxYGgFPMPJUSNR:matrix.org:$thread123:matrix.org",
        )
        assert chat_id == "!HLOQwxYGgFPMPJUSNR:matrix.org"
        assert thread_id == "$thread123:matrix.org"
        assert is_explicit is True

    def test_matrix_room_id_is_explicit(self):
        """Matrix room IDs (!) are recognized as explicit targets."""
        chat_id, thread_id, is_explicit = _parse_target_ref("matrix", "!HLOQwxYGgFPMPJUSNR:matrix.org")
        assert chat_id == "!HLOQwxYGgFPMPJUSNR:matrix.org"
        assert thread_id is None
        assert is_explicit is True

    def test_matrix_user_mxid_is_explicit(self):
        """Matrix user MXIDs (@) are recognized as explicit targets."""
        chat_id, thread_id, is_explicit = _parse_target_ref("matrix", "@hermes:matrix.org")
        assert chat_id == "@hermes:matrix.org"
        assert thread_id is None
        assert is_explicit is True

    def test_matrix_alias_is_not_explicit(self):
        """Matrix room aliases (#) are NOT explicit — they need resolution."""
        chat_id, thread_id, is_explicit = _parse_target_ref("matrix", "#general:matrix.org")
        assert chat_id is None
        assert is_explicit is False

    def test_matrix_prefix_only_matches_matrix_platform(self):
        """! and @ prefixes are only treated as explicit for the matrix platform."""
        chat_id, _, is_explicit = _parse_target_ref("telegram", "!something")
        assert is_explicit is False

        chat_id, _, is_explicit = _parse_target_ref("discord", "@someone")
        assert is_explicit is False


class TestParseTargetRefE164:
    """_parse_target_ref accepts E.164 phone numbers for phone-based platforms."""

    def test_signal_e164_preserves_plus_prefix(self):
        """signal:+E164 is explicit and preserves the leading '+' for signal-cli."""
        chat_id, thread_id, is_explicit = _parse_target_ref("signal", "+41791234567")
        assert chat_id == "+41791234567"
        assert thread_id is None
        assert is_explicit is True

    def test_signal_group_target_is_explicit(self):
        chat_id, thread_id, is_explicit = _parse_target_ref("signal", "  group:abc123  ")
        assert chat_id == "group:abc123"
        assert thread_id is None
        assert is_explicit is True

    def test_empty_signal_group_target_is_not_explicit(self):
        chat_id, thread_id, is_explicit = _parse_target_ref("signal", "  group:  ")
        assert chat_id is None
        assert thread_id is None
        assert is_explicit is False

    def test_sms_e164_is_explicit(self):
        chat_id, _, is_explicit = _parse_target_ref("sms", "+15551234567")
        assert chat_id == "+15551234567"
        assert is_explicit is True

    def test_whatsapp_e164_is_explicit(self):
        chat_id, _, is_explicit = _parse_target_ref("whatsapp", "+15551234567")
        assert chat_id == "+15551234567"
        assert is_explicit is True

    def test_photon_e164_is_explicit(self):
        chat_id, _, is_explicit = _parse_target_ref("photon", "+15551234567")
        assert chat_id == "+15551234567"
        assert is_explicit is True

    def test_signal_bare_digits_still_work(self):
        """Bare digit strings continue to match the generic numeric branch."""
        chat_id, _, is_explicit = _parse_target_ref("signal", "15551234567")
        assert chat_id == "15551234567"
        assert is_explicit is True

    def test_signal_invalid_e164_rejected(self):
        """Too-short, too-long, and non-numeric E.164 strings are not explicit."""
        assert _parse_target_ref("signal", "+123")[2] is False
        assert _parse_target_ref("signal", "+1234567890123456")[2] is False
        assert _parse_target_ref("signal", "+12abc4567890")[2] is False
        assert _parse_target_ref("signal", "+")[2] is False

    def test_e164_prefix_only_matches_phone_platforms(self):
        """'+' prefix must NOT be treated as explicit for non-phone platforms."""
        assert _parse_target_ref("telegram", "+15551234567")[2] is False
        assert _parse_target_ref("discord", "+15551234567")[2] is False
        assert _parse_target_ref("matrix", "+15551234567")[2] is False


class TestParseTargetRefWhatsAppJID:
    """_parse_target_ref accepts native WhatsApp JIDs as explicit targets.

    Regression: group JIDs (``<id>@g.us``) and linked-identity JIDs
    (``<id>@lid``) matched no branch and fell through to home-channel
    resolution, so ``send_message(target="whatsapp:<group-jid>")`` silently
    delivered to the configured home DM instead of the requested group.
    """

    def test_group_jid_is_explicit(self):
        chat_id, thread_id, is_explicit = _parse_target_ref(
            "whatsapp", "120363408391911677@g.us"
        )
        assert chat_id == "120363408391911677@g.us"
        assert thread_id is None
        assert is_explicit is True

    def test_user_jid_is_explicit(self):
        chat_id, _, is_explicit = _parse_target_ref(
            "whatsapp", "19255551234@s.whatsapp.net"
        )
        assert chat_id == "19255551234@s.whatsapp.net"
        assert is_explicit is True

    def test_lid_jid_is_explicit(self):
        chat_id, _, is_explicit = _parse_target_ref(
            "whatsapp", "149606612619433@lid"
        )
        assert chat_id == "149606612619433@lid"
        assert is_explicit is True

    def test_broadcast_and_newsletter_jids_are_explicit(self):
        assert _parse_target_ref("whatsapp", "status@broadcast")[2] is True
        assert _parse_target_ref("whatsapp", "120363000000000000@newsletter")[2] is True

    def test_whatsapp_e164_still_explicit_alongside_jids(self):
        """The pre-existing '+'-prefixed E.164 path must keep working."""
        chat_id, _, is_explicit = _parse_target_ref("whatsapp", "+15551234567")
        assert chat_id == "+15551234567"
        assert is_explicit is True

    def test_jid_suffix_only_matches_whatsapp(self):
        """WhatsApp JID suffixes must NOT be treated as explicit elsewhere."""
        assert _parse_target_ref("telegram", "120363408391911677@g.us")[2] is False
        assert _parse_target_ref("signal", "149606612619433@lid")[2] is False

    def test_non_jid_whatsapp_target_falls_through(self):
        """A bare friendly name is not a JID — it must fall through to
        directory resolution (returns not-explicit so the caller can resolve)."""
        assert _parse_target_ref("whatsapp", "general")[2] is False


class TestParseTargetRefSlack:
    """_parse_target_ref recognizes Slack channel/user IDs as explicit."""

    def test_thread_target_is_explicit(self):
        chat_id, thread_id, is_explicit = _parse_target_ref("slack", "C0B0QV5434G:171.000001")
        assert chat_id == "C0B0QV5434G"
        assert thread_id == "171.000001"
        assert is_explicit is True

    def test_public_channel_id_is_explicit(self):
        chat_id, thread_id, is_explicit = _parse_target_ref("slack", "C0B0QV5434G")
        assert chat_id == "C0B0QV5434G"
        assert thread_id is None
        assert is_explicit is True

    def test_private_channel_id_is_explicit(self):
        assert _parse_target_ref("slack", "G123ABCDEF")[2] is True

    def test_dm_id_is_explicit(self):
        assert _parse_target_ref("slack", "D123ABCDEF")[2] is True

    def test_user_id_is_not_explicit(self):
        """Slack user IDs (U...) and workspace IDs (W...) are NOT explicit send
        targets. chat.postMessage rejects them — a DM must be opened first via
        conversations.open to obtain a D... conversation ID.
        """
        assert _parse_target_ref("slack", "U123ABCDEF")[2] is False
        assert _parse_target_ref("slack", "W123ABCDEF")[2] is False

    def test_whitespace_is_stripped(self):
        chat_id, _, is_explicit = _parse_target_ref("slack", "  C0B0QV5434G  ")
        assert chat_id == "C0B0QV5434G"
        assert is_explicit is True

    def test_lowercase_or_short_id_is_not_explicit(self):
        assert _parse_target_ref("slack", "c0b0qv5434g")[2] is False
        assert _parse_target_ref("slack", "C123")[2] is False
        assert _parse_target_ref("slack", "X0B0QV5434G")[2] is False

    def test_slack_id_not_explicit_for_other_platforms(self):
        assert _parse_target_ref("discord", "C0B0QV5434G")[2] is False
        assert _parse_target_ref("telegram", "C0B0QV5434G")[2] is False


class TestParseTargetRefEmail:
    """_parse_target_ref recognizes email addresses as explicit for the email platform."""

    def test_standard_email_is_explicit(self):
        chat_id, thread_id, is_explicit = _parse_target_ref("email", "user@example.com")
        assert chat_id == "user@example.com"
        assert thread_id is None
        assert is_explicit is True

    def test_email_with_dots_in_local_part(self):
        chat_id, _, is_explicit = _parse_target_ref("email", "first.last@example.co.uk")
        assert chat_id == "first.last@example.co.uk"
        assert is_explicit is True

    def test_email_with_plus_tag(self):
        chat_id, _, is_explicit = _parse_target_ref("email", "user+tag@gmail.com")
        assert chat_id == "user+tag@gmail.com"
        assert is_explicit is True

    def test_email_strips_whitespace(self):
        chat_id, _, is_explicit = _parse_target_ref("email", "  user@example.com  ")
        assert chat_id == "user@example.com"
        assert is_explicit is True

    def test_invalid_email_not_explicit(self):
        assert _parse_target_ref("email", "not-an-email")[2] is False
        assert _parse_target_ref("email", "@example.com")[2] is False
        assert _parse_target_ref("email", "user@")[2] is False
        assert _parse_target_ref("email", "user@.com")[2] is False

    def test_email_not_explicit_for_other_platforms(self):
        assert _parse_target_ref("telegram", "user@example.com")[2] is False
        assert _parse_target_ref("discord", "user@example.com")[2] is False
        assert _parse_target_ref("slack", "user@example.com")[2] is False


class TestEmailHomeChannelErrorHint:
    """The no-home-channel error for email points at the real env var.

    Email reads its home channel from EMAIL_HOME_ADDRESS (gateway/config.py),
    not the generic EMAIL_HOME_CHANNEL. The error guidance must name the
    variable that is actually consulted so users who follow it succeed.
    """

    def test_email_error_names_email_home_address(self):
        email_cfg = SimpleNamespace(enabled=True, token="", extra={})
        config = SimpleNamespace(
            platforms={Platform.EMAIL: email_cfg},
            get_home_channel=lambda _platform: None,
        )
        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "email",
                        "message": "hi",
                    }
                )
            )
        assert "EMAIL_HOME_ADDRESS" in result["error"]
        assert "EMAIL_HOME_CHANNEL" not in result["error"]

    def test_non_email_platform_keeps_generic_home_channel_hint(self):
        telegram_cfg = SimpleNamespace(enabled=True, token="***", extra={})
        config = SimpleNamespace(
            platforms={Platform.TELEGRAM: telegram_cfg},
            get_home_channel=lambda _platform: None,
        )
        with patch("gateway.config.load_gateway_config", return_value=config), \
             patch("tools.interrupt.is_interrupted", return_value=False):
            result = json.loads(
                send_message_tool(
                    {
                        "action": "send",
                        "target": "telegram",
                        "message": "hi",
                    }
                )
            )
        assert "TELEGRAM_HOME_CHANNEL" in result["error"]


class TestSendDiscordThreadId:
    """_send_discord uses thread_id when provided."""

    @staticmethod
    def _build_mock(response_status, response_data=None, response_text="error body"):
        """Build a properly-structured aiohttp mock chain.

        session.post() returns a context manager yielding mock_resp.
        """
        mock_resp = MagicMock()
        mock_resp.status = response_status
        mock_resp.json = AsyncMock(return_value=response_data or {"id": "msg123"})
        mock_resp.text = AsyncMock(return_value=response_text)

        # mock_resp as async context manager (for "async with session.post(...) as resp")
        mock_resp.__aenter__ = AsyncMock(return_value=mock_resp)
        mock_resp.__aexit__ = AsyncMock(return_value=None)

        mock_session = MagicMock()
        mock_session.__aenter__ = AsyncMock(return_value=mock_session)
        mock_session.__aexit__ = AsyncMock(return_value=None)
        mock_session.post = MagicMock(return_value=mock_resp)

        return mock_session, mock_resp

    def _run(self, token, chat_id, message, thread_id=None):
        return asyncio.run(_send_discord(token, chat_id, message, thread_id=thread_id))

    def test_without_thread_id_uses_chat_id_endpoint(self):
        """When no thread_id, sends to /channels/{chat_id}/messages."""
        mock_session, _ = self._build_mock(200)
        with patch("aiohttp.ClientSession", return_value=mock_session):
            self._run("tok", "111222333", "hello world")
        call_url = mock_session.post.call_args.args[0]
        assert call_url == "https://discord.com/api/v10/channels/111222333/messages"

    def test_with_thread_id_uses_thread_endpoint(self):
        """When thread_id is provided, sends to /channels/{thread_id}/messages."""
        mock_session, _ = self._build_mock(200)
        with patch("aiohttp.ClientSession", return_value=mock_session):
            self._run("tok", "999888777", "hello from thread", thread_id="555444333")
        call_url = mock_session.post.call_args.args[0]
        assert call_url == "https://discord.com/api/v10/channels/555444333/messages"

    def test_success_returns_message_id(self):
        """Successful send returns the Discord message ID."""
        mock_session, _ = self._build_mock(200, response_data={"id": "9876543210"})
        with patch("aiohttp.ClientSession", return_value=mock_session):
            result = self._run("tok", "111", "hi", thread_id="999")
        assert result["success"] is True
        assert result["message_id"] == "9876543210"
        assert result["chat_id"] == "111"

    def test_error_status_returns_error_dict(self):
        """Non-200/201 responses return an error dict."""
        mock_session, _ = self._build_mock(403, response_data={"message": "Forbidden"})
        with patch("aiohttp.ClientSession", return_value=mock_session):
            result = self._run("tok", "111", "hi")
        assert "error" in result
        assert "403" in result["error"]

    def test_success_response_json_read_is_bounded(self):
        """Standalone Discord sends parse success JSON through the bounded reader."""
        body = b'{"id":"bounded-json"}'
        response = _StreamingAiohttpResponse(200, body)
        session = _StreamingAiohttpSession(response)

        with patch("aiohttp.ClientSession", return_value=session):
            result = self._run("tok", "111", "hi", thread_id="999")

        assert result["success"] is True
        assert result["message_id"] == "bounded-json"
        assert response.content.read_sizes[0] == _DISCORD_STANDALONE_JSON_BODY_LIMIT_BYTES + 1
        response.json.assert_not_awaited()
        response.text.assert_not_awaited()

    def test_error_response_text_read_is_bounded(self):
        """Oversized Discord API error bodies are capped before formatting."""
        body = b"E" * (_DISCORD_STANDALONE_ERROR_BODY_LIMIT_BYTES + 1024)
        response = _StreamingAiohttpResponse(500, body)
        session = _StreamingAiohttpSession(response)

        with patch("aiohttp.ClientSession", return_value=session):
            result = self._run("tok", "111", "hi", thread_id="999")

        assert "error" in result
        assert "500" in result["error"]
        assert response.content.read_sizes[0] == _DISCORD_STANDALONE_ERROR_BODY_LIMIT_BYTES + 1
        assert response.closed is True
        response.json.assert_not_awaited()
        response.text.assert_not_awaited()
        prefix = "Discord API error (500): "
        assert len(result["error"].encode("utf-8")) <= (
            len(prefix.encode("utf-8")) + _DISCORD_STANDALONE_ERROR_BODY_LIMIT_BYTES
        )


class TestSendToPlatformDiscordThread:
    """_send_to_platform passes thread_id through to _send_discord."""

    def test_discord_thread_id_passed_to_send_discord(self):
        """Discord platform with thread_id passes it to _send_discord."""
        send_mock = AsyncMock(return_value={"success": True, "message_id": "1"})

        with _patch_discord_sender(send_mock):
            result = asyncio.run(
                _send_to_platform(
                    Platform.DISCORD,
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "-1001234567890",
                    "hello thread",
                    thread_id="17585",
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once()
        _, call_kwargs = send_mock.await_args
        assert call_kwargs["thread_id"] == "17585"

    def test_discord_no_thread_id_when_not_provided(self):
        """Discord platform without thread_id passes None."""
        send_mock = AsyncMock(return_value={"success": True, "message_id": "1"})

        with _patch_discord_sender(send_mock):
            result = asyncio.run(
                _send_to_platform(
                    Platform.DISCORD,
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "9876543210",
                    "hello channel",
                )
            )

        send_mock.assert_awaited_once()
        _, call_kwargs = send_mock.await_args
        assert call_kwargs["thread_id"] is None


# ---------------------------------------------------------------------------
# Discord media attachment support
# ---------------------------------------------------------------------------


class TestSendDiscordMedia:
    """_send_discord uploads media files via multipart/form-data."""

    @staticmethod
    def _build_mock(response_status, response_data=None, response_text="error body"):
        """Build a properly-structured aiohttp mock chain."""
        mock_resp = MagicMock()
        mock_resp.status = response_status
        mock_resp.json = AsyncMock(return_value=response_data or {"id": "msg123"})
        mock_resp.text = AsyncMock(return_value=response_text)
        mock_resp.__aenter__ = AsyncMock(return_value=mock_resp)
        mock_resp.__aexit__ = AsyncMock(return_value=None)

        mock_session = MagicMock()
        mock_session.__aenter__ = AsyncMock(return_value=mock_session)
        mock_session.__aexit__ = AsyncMock(return_value=None)
        mock_session.post = MagicMock(return_value=mock_resp)

        return mock_session, mock_resp

    def test_text_and_media_sends_both(self, tmp_path):
        """Text message is sent first, then each media file as multipart."""
        img = tmp_path / "photo.png"
        img.write_bytes(b"\x89PNG fake image data")

        mock_session, _ = self._build_mock(200, {"id": "msg999"})
        with patch("aiohttp.ClientSession", return_value=mock_session):
            result = asyncio.run(
                _send_discord("tok", "111", "hello", media_files=[(str(img), False)])
            )

        assert result["success"] is True
        assert result["message_id"] == "msg999"
        # Two POSTs: one text JSON, one multipart upload
        assert mock_session.post.call_count == 2

    def test_media_only_skips_text_post(self, tmp_path):
        """When message is empty and media is present, text POST is skipped."""
        img = tmp_path / "photo.png"
        img.write_bytes(b"\x89PNG fake image data")

        mock_session, _ = self._build_mock(200, {"id": "media_only"})
        with patch("aiohttp.ClientSession", return_value=mock_session):
            result = asyncio.run(
                _send_discord("tok", "222", "  ", media_files=[(str(img), False)])
            )

        assert result["success"] is True
        # Only one POST: the media upload (text was whitespace-only)
        assert mock_session.post.call_count == 1

    def test_missing_media_file_collected_as_warning(self):
        """Non-existent media paths produce warnings but don't fail."""
        mock_session, _ = self._build_mock(200, {"id": "txt_ok"})
        with patch("aiohttp.ClientSession", return_value=mock_session):
            result = asyncio.run(
                _send_discord("tok", "333", "hello", media_files=[("/nonexistent/file.png", False)])
            )

        assert result["success"] is True
        assert "warnings" in result
        assert any("not found" in w for w in result["warnings"])
        # Only the text POST was made, media was skipped
        assert mock_session.post.call_count == 1

    def test_media_upload_failure_collected_as_warning(self, tmp_path):
        """Failed media upload becomes a warning, text still succeeds."""
        img = tmp_path / "photo.png"
        img.write_bytes(b"\x89PNG fake image data")

        # First call (text) succeeds, second call (media) returns 413
        text_resp = MagicMock()
        text_resp.status = 200
        text_resp.json = AsyncMock(return_value={"id": "txt_ok"})
        text_resp.__aenter__ = AsyncMock(return_value=text_resp)
        text_resp.__aexit__ = AsyncMock(return_value=None)

        media_resp = MagicMock()
        media_resp.status = 413
        media_resp.text = AsyncMock(return_value="Request Entity Too Large")
        media_resp.__aenter__ = AsyncMock(return_value=media_resp)
        media_resp.__aexit__ = AsyncMock(return_value=None)

        mock_session = MagicMock()
        mock_session.__aenter__ = AsyncMock(return_value=mock_session)
        mock_session.__aexit__ = AsyncMock(return_value=None)
        mock_session.post = MagicMock(side_effect=[text_resp, media_resp])

        with patch("aiohttp.ClientSession", return_value=mock_session):
            result = asyncio.run(
                _send_discord("tok", "444", "hello", media_files=[(str(img), False)])
            )

        assert result["success"] is True
        assert result["message_id"] == "txt_ok"
        assert "warnings" in result
        assert any("413" in w for w in result["warnings"])

    def test_no_text_no_media_returns_error(self):
        """Empty text with no media returns error dict."""
        mock_session, _ = self._build_mock(200)
        with patch("aiohttp.ClientSession", return_value=mock_session):
            result = asyncio.run(
                _send_discord("tok", "555", "", media_files=[])
            )

        # Text is empty but media_files is empty, so text POST fires
        # (the "skip text if media present" condition isn't met)
        assert result["success"] is True

    def test_multiple_media_files_uploaded_separately(self, tmp_path):
        """Each media file gets its own multipart POST."""
        img1 = tmp_path / "a.png"
        img1.write_bytes(b"img1")
        img2 = tmp_path / "b.jpg"
        img2.write_bytes(b"img2")

        mock_session, _ = self._build_mock(200, {"id": "last"})
        with patch("aiohttp.ClientSession", return_value=mock_session):
            result = asyncio.run(
                _send_discord("tok", "666", "hi", media_files=[
                    (str(img1), False), (str(img2), False)
                ])
            )

        assert result["success"] is True
        # 1 text POST + 2 media POSTs = 3
        assert mock_session.post.call_count == 3


class TestSendToPlatformDiscordMedia:
    """_send_to_platform routes Discord media correctly."""

    def test_media_files_passed_on_last_chunk_only(self):
        """Discord media_files are only passed on the final chunk."""
        call_log = []

        async def mock_send_discord(token, chat_id, message, thread_id=None, media_files=None):
            call_log.append({"message": message, "media_files": media_files or []})
            return {"success": True, "platform": "discord", "chat_id": chat_id, "message_id": "1"}

        # A message long enough to get chunked (Discord limit is 2000)
        long_msg = "A" * 1900 + " " + "B" * 1900

        with _patch_discord_sender(AsyncMock(side_effect=mock_send_discord)):
            result = asyncio.run(
                _send_to_platform(
                    Platform.DISCORD,
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "999",
                    long_msg,
                    media_files=[("/fake/img.png", False)],
                )
            )

        assert result["success"] is True
        assert len(call_log) == 2  # Message was chunked
        assert call_log[0]["media_files"] == []  # First chunk: no media
        assert call_log[1]["media_files"] == [("/fake/img.png", False)]  # Last chunk: media attached

    def test_single_chunk_gets_media(self):
        """Short message + single image rides as the media caption."""
        send_mock = AsyncMock(return_value={"success": True, "message_id": "1"})

        with _patch_discord_sender(send_mock):
            result = asyncio.run(
                _send_to_platform(
                    Platform.DISCORD,
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "888",
                    "short message",
                    media_files=[("/fake/img.png", False)],
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once()
        call_kwargs = send_mock.await_args.kwargs
        assert call_kwargs["media_files"] == [("/fake/img.png", False)]
        # Text rides as the caption, not a separate positional message body.
        assert call_kwargs.get("caption") == "short message"
        assert send_mock.await_args.args[2] == ""


class TestSendMatrixUrlEncoding:
    """The matrix plugin's _standalone_send URL-encodes Matrix room IDs in the
    API path (was tools.send_message_tool._send_matrix before #41112)."""

    def test_room_id_is_percent_encoded_in_url(self):
        """Matrix room IDs with ! and : are percent-encoded in the PUT URL."""

        mock_resp = MagicMock()
        mock_resp.status = 200
        mock_resp.json = AsyncMock(return_value={"event_id": "$evt123"})
        mock_resp.__aenter__ = AsyncMock(return_value=mock_resp)
        mock_resp.__aexit__ = AsyncMock(return_value=None)

        mock_session = MagicMock()
        mock_session.put = MagicMock(return_value=mock_resp)
        mock_session.__aenter__ = AsyncMock(return_value=mock_session)
        mock_session.__aexit__ = AsyncMock(return_value=None)

        with patch("aiohttp.ClientSession", return_value=mock_session):
            from plugins.platforms.matrix.adapter import _standalone_send
            result = asyncio.get_event_loop().run_until_complete(
                _standalone_send(
                    SimpleNamespace(token="test_token", extra={"homeserver": "https://matrix.example.org"}),
                    "!HLOQwxYGgFPMPJUSNR:matrix.org",
                    "hello",
                )
            )

        assert result["success"] is True
        # Verify the URL was called with percent-encoded room ID
        put_url = mock_session.put.call_args[0][0]
        assert "%21HLOQwxYGgFPMPJUSNR%3Amatrix.org" in put_url
        assert "!HLOQwxYGgFPMPJUSNR:matrix.org" not in put_url


# ---------------------------------------------------------------------------
# Tests for _derive_forum_thread_name
# ---------------------------------------------------------------------------


class TestDeriveForumThreadName:
    def test_single_line_message(self):
        assert _derive_forum_thread_name("Hello world") == "Hello world"

    def test_multi_line_uses_first_line(self):
        assert _derive_forum_thread_name("First line\nSecond line") == "First line"

    def test_strips_markdown_heading(self):
        assert _derive_forum_thread_name("## My Heading") == "My Heading"

    def test_strips_multiple_hash_levels(self):
        assert _derive_forum_thread_name("### Deep heading") == "Deep heading"

    def test_empty_message_falls_back_to_default(self):
        assert _derive_forum_thread_name("") == "New Post"

    def test_whitespace_only_falls_back(self):
        assert _derive_forum_thread_name("   \n  ") == "New Post"

    def test_hash_only_falls_back(self):
        assert _derive_forum_thread_name("###") == "New Post"

    def test_truncates_to_100_chars(self):
        long_title = "A" * 200
        result = _derive_forum_thread_name(long_title)
        assert len(result) == 100

    def test_strips_whitespace_around_first_line(self):
        assert _derive_forum_thread_name("  Title  \nBody") == "Title"


# ---------------------------------------------------------------------------
# Tests for _send_discord with forum channel support
# ---------------------------------------------------------------------------


class TestSendDiscordForum:
    """_send_discord creates thread posts for forum channels."""

    @staticmethod
    def _build_mock(response_status, response_data=None, response_text="error body"):
        mock_resp = MagicMock()
        mock_resp.status = response_status
        mock_resp.json = AsyncMock(return_value=response_data or {})
        mock_resp.text = AsyncMock(return_value=response_text)
        mock_resp.__aenter__ = AsyncMock(return_value=mock_resp)
        mock_resp.__aexit__ = AsyncMock(return_value=None)

        mock_session = MagicMock()
        mock_session.__aenter__ = AsyncMock(return_value=mock_session)
        mock_session.__aexit__ = AsyncMock(return_value=None)
        mock_session.post = MagicMock(return_value=mock_resp)
        mock_session.get = MagicMock(return_value=mock_resp)

        return mock_session, mock_resp

    def test_directory_forum_creates_thread(self):
        """Directory says 'forum' — creates a thread post."""
        thread_data = {
            "id": "t123",
            "message": {"id": "m456"},
        }
        mock_session, _ = self._build_mock(200, response_data=thread_data)

        with patch("aiohttp.ClientSession", return_value=mock_session), \
             patch("gateway.channel_directory.lookup_channel_type", return_value="forum"):
            result = asyncio.run(
                _send_discord("tok", "forum_ch", "Hello forum")
            )

        assert result["success"] is True
        assert result["thread_id"] == "t123"
        assert result["message_id"] == "m456"
        # Should POST to threads endpoint, not messages
        call_url = mock_session.post.call_args.args[0]
        assert "/threads" in call_url
        assert "/messages" not in call_url

    def test_directory_forum_skips_probe(self):
        """When directory says 'forum', no GET probe is made."""
        thread_data = {"id": "t123", "message": {"id": "m456"}}
        mock_session, _ = self._build_mock(200, response_data=thread_data)

        with patch("aiohttp.ClientSession", return_value=mock_session), \
             patch("gateway.channel_directory.lookup_channel_type", return_value="forum"):
            asyncio.run(
                _send_discord("tok", "forum_ch", "Hello")
            )

        # get() should never be called — directory resolved the type
        mock_session.get.assert_not_called()

    def test_directory_channel_skips_forum(self):
        """When directory says 'channel', sends via normal messages endpoint."""
        mock_session, _ = self._build_mock(200, response_data={"id": "msg1"})

        with patch("aiohttp.ClientSession", return_value=mock_session), \
             patch("gateway.channel_directory.lookup_channel_type", return_value="channel"):
            result = asyncio.run(
                _send_discord("tok", "ch1", "Hello")
            )

        assert result["success"] is True
        call_url = mock_session.post.call_args.args[0]
        assert "/messages" in call_url
        assert "/threads" not in call_url

    def test_directory_none_probes_and_detects_forum(self):
        """When directory has no entry, probes GET /channels/{id} and detects type 15."""
        probe_resp = MagicMock()
        probe_resp.status = 200
        probe_resp.json = AsyncMock(return_value={"type": 15})
        probe_resp.__aenter__ = AsyncMock(return_value=probe_resp)
        probe_resp.__aexit__ = AsyncMock(return_value=None)

        thread_data = {"id": "t999", "message": {"id": "m888"}}
        thread_resp = MagicMock()
        thread_resp.status = 200
        thread_resp.json = AsyncMock(return_value=thread_data)
        thread_resp.text = AsyncMock(return_value="")
        thread_resp.__aenter__ = AsyncMock(return_value=thread_resp)
        thread_resp.__aexit__ = AsyncMock(return_value=None)

        probe_session = MagicMock()
        probe_session.__aenter__ = AsyncMock(return_value=probe_session)
        probe_session.__aexit__ = AsyncMock(return_value=None)
        probe_session.get = MagicMock(return_value=probe_resp)

        thread_session = MagicMock()
        thread_session.__aenter__ = AsyncMock(return_value=thread_session)
        thread_session.__aexit__ = AsyncMock(return_value=None)
        thread_session.post = MagicMock(return_value=thread_resp)

        session_iter = iter([probe_session, thread_session])

        with patch("aiohttp.ClientSession", side_effect=lambda **kw: next(session_iter)), \
             patch("gateway.channel_directory.lookup_channel_type", return_value=None):
            result = asyncio.run(
                _send_discord("tok", "forum_ch", "Hello probe")
            )

        assert result["success"] is True
        assert result["thread_id"] == "t999"

    def test_directory_lookup_exception_falls_through_to_probe(self):
        """When lookup_channel_type raises, falls through to API probe."""
        mock_session, _ = self._build_mock(200, response_data={"id": "msg1"})

        with patch("aiohttp.ClientSession", return_value=mock_session), \
             patch("gateway.channel_directory.lookup_channel_type", side_effect=Exception("io error")):
            result = asyncio.run(
                _send_discord("tok", "ch1", "Hello")
            )

        assert result["success"] is True
        # Falls through to probe (GET)
        mock_session.get.assert_called_once()

    def test_forum_thread_creation_error(self):
        """Forum thread creation returning non-200/201 returns an error dict."""
        mock_session, _ = self._build_mock(403, response_text="Forbidden")

        with patch("aiohttp.ClientSession", return_value=mock_session), \
             patch("gateway.channel_directory.lookup_channel_type", return_value="forum"):
            result = asyncio.run(
                _send_discord("tok", "forum_ch", "Hello")
            )

        assert "error" in result
        assert "403" in result["error"]



class TestSendToPlatformDiscordForum:
    """_send_to_platform delegates forum detection to _send_discord."""

    def test_send_to_platform_discord_delegates_to_send_discord(self):
        """Discord messages are routed through _send_discord, which handles forum detection."""
        send_mock = AsyncMock(return_value={"success": True, "message_id": "1"})

        with _patch_discord_sender(send_mock):
            result = asyncio.run(
                _send_to_platform(
                    Platform.DISCORD,
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "forum_ch",
                    "Hello forum",
                )
            )

        assert result["success"] is True
        send_mock.assert_awaited_once_with(
            "tok", "forum_ch", "Hello forum", media_files=[], thread_id=None,
        )

    def test_send_to_platform_discord_with_thread_id(self):
        """Thread ID is still passed through when sending to Discord."""
        send_mock = AsyncMock(return_value={"success": True, "message_id": "1"})

        with _patch_discord_sender(send_mock):
            result = asyncio.run(
                _send_to_platform(
                    Platform.DISCORD,
                    SimpleNamespace(enabled=True, token="tok", extra={}),
                    "ch1",
                    "Hello thread",
                    thread_id="17585",
                )
            )

        assert result["success"] is True
        _, call_kwargs = send_mock.await_args
        assert call_kwargs["thread_id"] == "17585"


# ---------------------------------------------------------------------------
# Tests for _send_discord forum + media multipart upload
# ---------------------------------------------------------------------------


class TestSendDiscordForumMedia:
    """_send_discord uploads media as part of the starter message when the target is a forum."""

    @staticmethod
    def _build_thread_resp(thread_id="th_999", msg_id="msg_500"):
        resp = MagicMock()
        resp.status = 201
        resp.json = AsyncMock(return_value={"id": thread_id, "message": {"id": msg_id}})
        resp.text = AsyncMock(return_value="")
        resp.__aenter__ = AsyncMock(return_value=resp)
        resp.__aexit__ = AsyncMock(return_value=None)
        return resp

    def test_forum_with_media_uses_multipart(self, tmp_path, monkeypatch):
        """Forum + media → single multipart POST to /threads carrying the starter + files."""
        from tools import send_message_tool as smt

        img = tmp_path / "photo.png"
        img.write_bytes(b"\x89PNGbytes")

        monkeypatch.setattr(smt, "lookup_channel_type", lambda p, cid: "forum", raising=False)
        monkeypatch.setattr(
            "gateway.channel_directory.lookup_channel_type", lambda p, cid: "forum"
        )

        thread_resp = self._build_thread_resp()
        session = MagicMock()
        session.__aenter__ = AsyncMock(return_value=session)
        session.__aexit__ = AsyncMock(return_value=None)
        session.post = MagicMock(return_value=thread_resp)

        post_calls = []
        orig_post = session.post

        def track_post(url, **kwargs):
            post_calls.append({"url": url, "kwargs": kwargs})
            return thread_resp

        session.post = MagicMock(side_effect=track_post)

        with patch("aiohttp.ClientSession", return_value=session):
            result = asyncio.run(
                _send_discord("tok", "forum_ch", "Thread title\nbody", media_files=[(str(img), False)])
            )

        assert result["success"] is True
        assert result["thread_id"] == "th_999"
        assert result["message_id"] == "msg_500"
        # Exactly one POST — the combined thread-creation + attachments call
        assert len(post_calls) == 1
        assert post_calls[0]["url"].endswith("/threads")
        # Multipart form, not JSON
        assert post_calls[0]["kwargs"].get("data") is not None
        assert post_calls[0]["kwargs"].get("json") is None

    def test_forum_without_media_still_json_only(self, tmp_path, monkeypatch):
        """Forum + no media → JSON POST (no multipart overhead)."""
        monkeypatch.setattr(
            "gateway.channel_directory.lookup_channel_type", lambda p, cid: "forum"
        )

        thread_resp = self._build_thread_resp("t1", "m1")
        session = MagicMock()
        session.__aenter__ = AsyncMock(return_value=session)
        session.__aexit__ = AsyncMock(return_value=None)

        post_calls = []

        def track_post(url, **kwargs):
            post_calls.append({"url": url, "kwargs": kwargs})
            return thread_resp

        session.post = MagicMock(side_effect=track_post)

        with patch("aiohttp.ClientSession", return_value=session):
            result = asyncio.run(_send_discord("tok", "forum_ch", "Hello forum"))

        assert result["success"] is True
        assert len(post_calls) == 1
        # JSON path, no multipart
        assert post_calls[0]["kwargs"].get("json") is not None
        assert post_calls[0]["kwargs"].get("data") is None

    def test_forum_missing_media_file_collected_as_warning(self, tmp_path, monkeypatch):
        """Missing media files produce warnings but the thread is still created."""
        monkeypatch.setattr(
            "gateway.channel_directory.lookup_channel_type", lambda p, cid: "forum"
        )

        thread_resp = self._build_thread_resp()
        session = MagicMock()
        session.__aenter__ = AsyncMock(return_value=session)
        session.__aexit__ = AsyncMock(return_value=None)
        session.post = MagicMock(return_value=thread_resp)

        with patch("aiohttp.ClientSession", return_value=session):
            result = asyncio.run(
                _send_discord(
                    "tok", "forum_ch", "hi",
                    media_files=[("/nonexistent/does-not-exist.png", False)],
                )
            )

        assert result["success"] is True
        assert "warnings" in result
        assert any("not found" in w for w in result["warnings"])


# ---------------------------------------------------------------------------
# Tests for the process-local forum-probe cache
# ---------------------------------------------------------------------------


class TestForumProbeCache:
    """_DISCORD_CHANNEL_TYPE_PROBE_CACHE memoizes forum detection results."""

    def setup_method(self):
        from plugins.platforms.discord import adapter as discord_adapter
        discord_adapter._DISCORD_CHANNEL_TYPE_PROBE_CACHE.clear()

    def test_cache_round_trip(self):
        assert _probe_is_forum_cached("xyz") is None
        _remember_channel_is_forum("xyz", True)
        assert _probe_is_forum_cached("xyz") is True
        _remember_channel_is_forum("xyz", False)
        assert _probe_is_forum_cached("xyz") is False

    def test_probe_result_is_memoized(self, monkeypatch):
        """An API-probed channel type is cached so subsequent sends skip the probe."""
        monkeypatch.setattr(
            "gateway.channel_directory.lookup_channel_type", lambda p, cid: None
        )

        # First probe response: type=15 (forum)
        probe_resp = MagicMock()
        probe_resp.status = 200
        probe_resp.json = AsyncMock(return_value={"type": 15})
        probe_resp.__aenter__ = AsyncMock(return_value=probe_resp)
        probe_resp.__aexit__ = AsyncMock(return_value=None)

        thread_resp = MagicMock()
        thread_resp.status = 201
        thread_resp.json = AsyncMock(return_value={"id": "t1", "message": {"id": "m1"}})
        thread_resp.__aenter__ = AsyncMock(return_value=thread_resp)
        thread_resp.__aexit__ = AsyncMock(return_value=None)

        probe_session = MagicMock()
        probe_session.__aenter__ = AsyncMock(return_value=probe_session)
        probe_session.__aexit__ = AsyncMock(return_value=None)
        probe_session.get = MagicMock(return_value=probe_resp)

        thread_session = MagicMock()
        thread_session.__aenter__ = AsyncMock(return_value=thread_session)
        thread_session.__aexit__ = AsyncMock(return_value=None)
        thread_session.post = MagicMock(return_value=thread_resp)

        # Two _send_discord calls: first does probe + thread-create; second should skip probe
        from plugins.platforms.discord import adapter as discord_adapter

        sessions_created = []

        def session_factory(**kwargs):
            # Alternate: each new ClientSession() call returns a probe_session, thread_session pair
            idx = len(sessions_created)
            sessions_created.append(idx)
            # Returns the same mocks; the real code opens a probe session then a thread session.
            # Hand out probe_session if this is the first time called within _send_discord,
            # otherwise thread_session.
            if idx % 2 == 0:
                return probe_session
            return thread_session

        with patch("aiohttp.ClientSession", side_effect=session_factory):
            result1 = asyncio.run(_send_discord("tok", "ch1", "first"))
        assert result1["success"] is True
        assert discord_adapter._probe_is_forum_cached("ch1") is True

        # Second call: cache hits, no new probe session needed. We need to only
        # return thread_session now since probe is skipped.
        sessions_created.clear()
        with patch("aiohttp.ClientSession", return_value=thread_session):
            result2 = asyncio.run(_send_discord("tok", "ch1", "second"))
        assert result2["success"] is True
        # Only one session opened (thread creation) — no probe session this time
        # (verified by not raising from our side_effect exhaustion)


# ---------------------------------------------------------------------------
# _send_signal — chunking + 429 retry (mirrors gateway adapter behavior)
# ---------------------------------------------------------------------------


class _FakeSignalHttp:
    """Stand-in for httpx.AsyncClient used as an async context manager.

    Pops a response from the queue per `post` call. Each entry is either
    a dict (returned from .json()) or an exception instance (raised).
    Captures (url, payload) per call.
    """

    def __init__(self, responses):
        self.responses = list(responses)
        self.calls = []

    def __call__(self, *_a, **_kw):
        return self

    async def __aenter__(self):
        return self

    async def __aexit__(self, *_a):
        return False

    async def post(self, url, json=None):
        self.calls.append({"url": url, "payload": json})
        if not self.responses:
            raise AssertionError("Unexpected extra POST")
        item = self.responses.pop(0)
        if isinstance(item, BaseException):
            raise item
        resp = SimpleNamespace(
            raise_for_status=lambda: None,
            json=lambda data=item: data,
        )
        return resp


def _install_signal_http(monkeypatch, fake):
    """Patch httpx.AsyncClient at the module level so the lazy import in
    _send_signal picks it up.
    """
    import httpx
    monkeypatch.setattr(httpx, "AsyncClient", fake)


def _patch_sendmsg_sleep_and_time(monkeypatch, capture: list):
    """Mock asyncio.sleep + time.monotonic in the signal_rate_limit
    module so the scheduler's acquire loop sees synthetic time advancing
    during sleep calls, and report_rpc_duration sees the same clock.

    Zero-second sleeps (event-loop yields from fake HTTP posts) are
    delegated to the real asyncio.sleep so they don't pollute the
    capture list.
    """
    import asyncio as _aio
    _real_sleep = _aio.sleep
    offset = [0.0]

    async def fake_sleep(seconds):
        if seconds > 0:
            capture.append(seconds)
            offset[0] += seconds
        else:
            await _real_sleep(0)

    monkeypatch.setattr(
        "gateway.platforms.signal_rate_limit.asyncio.sleep", fake_sleep
    )
    monkeypatch.setattr(
        "gateway.platforms.signal_rate_limit.time.monotonic", lambda: offset[0]
    )


class TestSendSignalChunking:
    def test_text_only_single_rpc(self, monkeypatch):
        fake = _FakeSignalHttp([{"result": {"timestamp": 1}}])
        _install_signal_http(monkeypatch, fake)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+15551234567"},
                "+15557654321",
                "hello",
            )
        )

        assert result["success"] is True
        assert result["platform"] == "signal"
        assert result["chat_id"].endswith("4321")
        assert len(fake.calls) == 1
        params = fake.calls[0]["payload"]["params"]
        assert params["message"] == "hello"
        assert "attachments" not in params
        assert "textStyle" not in params
        assert "textStyles" not in params

    def test_text_only_markdown_uses_singular_text_style(self, monkeypatch):
        fake = _FakeSignalHttp([{"result": {"timestamp": 1}}])
        _install_signal_http(monkeypatch, fake)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+155****4567"},
                "+155****4321",
                "**hello**",
            )
        )

        assert result["success"] is True
        params = fake.calls[0]["payload"]["params"]
        assert params["message"] == "hello"
        assert params["textStyle"] == "0:5:BOLD"
        assert "textStyles" not in params

    def test_text_only_multiple_styles_use_plural_text_styles(self, monkeypatch):
        fake = _FakeSignalHttp([{"result": {"timestamp": 1}}])
        _install_signal_http(monkeypatch, fake)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+155****4567"},
                "+155****4321",
                "**bold** and *italic*",
            )
        )

        assert result["success"] is True
        params = fake.calls[0]["payload"]["params"]
        assert params["message"] == "bold and italic"
        assert "textStyle" not in params
        assert params["textStyles"] == ["0:4:BOLD", "9:6:ITALIC"]

    def test_text_style_offsets_use_utf16_code_units(self, monkeypatch):
        fake = _FakeSignalHttp([{"result": {"timestamp": 1}}])
        _install_signal_http(monkeypatch, fake)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+155****4567"},
                "+155****4321",
                "🙂 **bold**",
            )
        )

        assert result["success"] is True
        params = fake.calls[0]["payload"]["params"]
        assert params["message"] == "🙂 bold"
        assert params["textStyle"] == "3:4:BOLD"

    def test_chunks_attachments_above_max(self, tmp_path, monkeypatch):
        """33 attachments → 2 batches; text only on first batch. Batch 1
        only needs 1 token and 18 remain after batch 0, so no sleep."""
        from gateway.platforms.signal_rate_limit import (
            SIGNAL_MAX_ATTACHMENTS_PER_MSG,
        )

        paths = []
        for i in range(33):
            p = tmp_path / f"img_{i}.png"
            p.write_bytes(b"\x89PNG" + b"\x00" * 16)
            paths.append((str(p), False))

        fake = _FakeSignalHttp([
            {"result": {"timestamp": 1}},   # batch 0
            {"result": {"timestamp": 2}},   # batch 1
        ])
        _install_signal_http(monkeypatch, fake)

        sleep_calls = []
        _patch_sendmsg_sleep_and_time(monkeypatch, sleep_calls)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+15551234567"},
                "+15557654321",
                "Caption goes here",
                media_files=paths,
            )
        )

        assert result["success"] is True
        assert len(fake.calls) == 2
        assert len(sleep_calls) == 0

        first = fake.calls[0]["payload"]["params"]
        assert first["message"] == "Caption goes here"
        assert len(first["attachments"]) == SIGNAL_MAX_ATTACHMENTS_PER_MSG
        assert "textStyle" not in first
        assert "textStyles" not in first

        second = fake.calls[1]["payload"]["params"]
        assert second["message"] == ""  # caption only on batch 0
        assert len(second["attachments"]) == 33 - SIGNAL_MAX_ATTACHMENTS_PER_MSG
        assert "textStyle" not in second
        assert "textStyles" not in second

    def test_caption_styles_only_apply_to_first_attachment_batch(self, tmp_path, monkeypatch):
        from gateway.platforms.signal_rate_limit import SIGNAL_MAX_ATTACHMENTS_PER_MSG

        paths = []
        for i in range(33):
            p = tmp_path / f"img_{i}.png"
            p.write_bytes(b"\x89PNG" + b"\x00" * 16)
            paths.append((str(p), False))

        fake = _FakeSignalHttp([
            {"result": {"timestamp": 1}},
            {"result": {"timestamp": 2}},
        ])
        _install_signal_http(monkeypatch, fake)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+155****4567"},
                "group:abc123",
                "**Bold** and *italic*",
                media_files=paths,
            )
        )

        assert result["success"] is True
        assert result["chat_id"] == "group:***"
        first = fake.calls[0]["payload"]["params"]
        assert first["groupId"] == "abc123"
        assert first["message"] == "Bold and italic"
        assert first["textStyles"] == ["0:4:BOLD", "9:6:ITALIC"]
        assert len(first["attachments"]) == SIGNAL_MAX_ATTACHMENTS_PER_MSG

        second = fake.calls[1]["payload"]["params"]
        assert second["groupId"] == "abc123"
        assert second["message"] == ""
        assert len(second["attachments"]) == 33 - SIGNAL_MAX_ATTACHMENTS_PER_MSG
        assert "textStyle" not in second
        assert "textStyles" not in second

    def test_full_followup_batch_emits_pacing_notice(self, tmp_path, monkeypatch):
        """64 attachments → 2 full batches. Batch 1 needs 14 more tokens
        than the 18 remaining after batch 0 — 56s wait crossing the 10s
        notice threshold."""
        from gateway.platforms.signal_rate_limit import (
            SIGNAL_MAX_ATTACHMENTS_PER_MSG,
            SIGNAL_RATE_LIMIT_BUCKET_CAPACITY,
            SIGNAL_RATE_LIMIT_DEFAULT_RETRY_AFTER,
        )

        paths = []
        for i in range(64):
            p = tmp_path / f"img_{i}.png"
            p.write_bytes(b"\x89PNG" + b"\x00" * 16)
            paths.append((str(p), False))

        fake = _FakeSignalHttp([
            {"result": {"timestamp": 1}},   # batch 0
            {"result": {"timestamp": 99}},  # pacing notice
            {"result": {"timestamp": 2}},   # batch 1
        ])
        _install_signal_http(monkeypatch, fake)

        sleep_calls = []
        _patch_sendmsg_sleep_and_time(monkeypatch, sleep_calls)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+15551234567"},
                "+15557654321",
                "",
                media_files=paths,
            )
        )

        assert result["success"] is True
        assert len(fake.calls) == 3
        notice = fake.calls[1]["payload"]["params"]
        assert "More images coming" in notice["message"]
        assert "attachments" not in notice
        # Batch 1 deficit: 32 - (50 - 32) = 14 tokens × 4s = 56s
        expected = (
            SIGNAL_MAX_ATTACHMENTS_PER_MSG
            - (SIGNAL_RATE_LIMIT_BUCKET_CAPACITY - SIGNAL_MAX_ATTACHMENTS_PER_MSG)
        ) * SIGNAL_RATE_LIMIT_DEFAULT_RETRY_AFTER
        assert sleep_calls == [pytest.approx(expected, abs=1.0)]

    def test_429_with_retry_after_drives_exact_backoff(self, tmp_path, monkeypatch):
        """signal-cli ≥ v0.14.3 surfaces Retry-After under
        error.data.response.results[*].retryAfterSeconds. The scheduler
        calibrates its refill rate from that value; the retry of n=1
        sleeps the per-token interval."""
        from gateway.platforms.signal_rate_limit import SIGNAL_RPC_ERROR_RATELIMIT

        p = tmp_path / "img.png"
        p.write_bytes(b"\x89PNG" + b"\x00" * 16)

        fake = _FakeSignalHttp([
            {
                "error": {
                    "code": SIGNAL_RPC_ERROR_RATELIMIT,
                    "message": "Failed to send message due to rate limiting",
                    "data": {
                        "response": {
                            "timestamp": 0,
                            "results": [
                                {"type": "RATE_LIMIT_FAILURE", "retryAfterSeconds": 42},
                            ],
                        }
                    },
                }
            },
            {"result": {"timestamp": 7}},
        ])
        _install_signal_http(monkeypatch, fake)

        sleep_calls = []
        _patch_sendmsg_sleep_and_time(monkeypatch, sleep_calls)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+15551234567"},
                "+15557654321",
                "",
                media_files=[(str(p), False)],
            )
        )

        assert result["success"] is True
        assert len(fake.calls) == 2  # initial + retry
        assert sleep_calls == [pytest.approx(42.0, abs=1.0)]

    def test_429_without_retry_after_falls_back_to_default(self, tmp_path, monkeypatch):
        """Older signal-cli (< v0.14.3) doesn't surface Retry-After.
        The scheduler keeps its default rate (1 token / 4s)."""
        from gateway.platforms.signal_rate_limit import SIGNAL_RATE_LIMIT_DEFAULT_RETRY_AFTER

        p = tmp_path / "img.png"
        p.write_bytes(b"\x89PNG" + b"\x00" * 16)

        fake = _FakeSignalHttp([
            {"error": {"message": "Failed: [429] Rate Limited"}},
            {"result": {"timestamp": 7}},
        ])
        _install_signal_http(monkeypatch, fake)

        sleep_calls = []
        _patch_sendmsg_sleep_and_time(monkeypatch, sleep_calls)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+15551234567"},
                "+15557654321",
                "",
                media_files=[(str(p), False)],
            )
        )

        assert result["success"] is True
        assert sleep_calls == [pytest.approx(SIGNAL_RATE_LIMIT_DEFAULT_RETRY_AFTER, abs=1.0)]

    def test_429_retry_exhaust_continues_to_next_batch(self, tmp_path, monkeypatch):
        """Both attempts on batch 0 fail; batch 1 still gets a chance.
        The scheduler's natural pacing (no more cooldown gate) lets the
        second batch through after its acquire wait."""
        from gateway.platforms.signal_rate_limit import SIGNAL_RPC_ERROR_RATELIMIT

        paths = []
        for i in range(33):  # forces 2 batches
            p = tmp_path / f"img_{i}.png"
            p.write_bytes(b"\x89PNG" + b"\x00" * 16)
            paths.append((str(p), False))

        rate_limit_err = {
            "error": {
                "code": SIGNAL_RPC_ERROR_RATELIMIT,
                "message": "Failed to send message due to rate limiting",
                "data": {
                    "response": {
                        "timestamp": 0,
                        "results": [
                            {"type": "RATE_LIMIT_FAILURE", "retryAfterSeconds": 4},
                        ],
                    }
                },
            }
        }

        fake = _FakeSignalHttp([
            rate_limit_err,                  # batch 0, attempt 1
            rate_limit_err,                  # batch 0, attempt 2 (exhaust)
            {"result": {"timestamp": 9}},    # batch 1 succeeds
        ])
        _install_signal_http(monkeypatch, fake)

        sleep_calls = []
        _patch_sendmsg_sleep_and_time(monkeypatch, sleep_calls)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+15551234567"},
                "+15557654321",
                "many",
                media_files=paths,
            )
        )

        # Partial success: batch 0 lost but batch 1 went through.
        assert result["success"] is True
        assert "warnings" in result
        assert any("rate-limited" in w for w in result["warnings"])
        # 2 attempts on batch 0 + 1 successful batch 1 = 3 calls
        assert len(fake.calls) == 3

    def test_non_rate_limit_error_returns_immediately(self, tmp_path, monkeypatch):
        """A non-429 RPC error should not retry — it returns an error result."""
        p = tmp_path / "img.png"
        p.write_bytes(b"\x89PNG" + b"\x00" * 16)

        fake = _FakeSignalHttp([
            {"error": {"message": "UntrustedIdentityException"}},
        ])
        _install_signal_http(monkeypatch, fake)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+15551234567"},
                "+15557654321",
                "",
                media_files=[(str(p), False)],
            )
        )

        assert "error" in result
        assert "UntrustedIdentityException" in result["error"]
        assert len(fake.calls) == 1  # no retry on non-429

    def test_skipped_missing_files_reported_in_warnings(self, tmp_path, monkeypatch):
        good = tmp_path / "ok.png"
        good.write_bytes(b"\x89PNG" + b"\x00" * 16)

        fake = _FakeSignalHttp([{"result": {"timestamp": 1}}])
        _install_signal_http(monkeypatch, fake)

        result = asyncio.run(
            _send_signal(
                {"http_url": "http://localhost:8080", "account": "+15551234567"},
                "+15557654321",
                "msg",
                media_files=[(str(good), False), (str(tmp_path / "missing.png"), False)],
            )
        )

        assert result["success"] is True
        assert "warnings" in result
        # Only the existing file made it into the RPC
        params = fake.calls[0]["payload"]["params"]
        assert len(params["attachments"]) == 1


# ── _send_via_adapter standalone fallback ────────────────────────────────


class _FakePlatform:
    """Stand-in for the gateway.config.Platform enum.  Holds the .value
    attribute consulted by ``_send_via_adapter`` for registry lookups."""

    def __init__(self, value):
        self.value = value


class TestSendViaAdapterStandaloneFallback:
    """Coverage for the out-of-process plugin-platform send path.

    When the gateway runner is not in this process (e.g. ``hermes cron``
    runs separately from ``hermes gateway``), ``_send_via_adapter`` should
    fall through to the plugin's ``standalone_sender_fn`` registered on
    its ``PlatformEntry``.  Without the hook, the existing error string
    is returned (with a more helpful tail).
    """

    @staticmethod
    def _make_entry(send_fn):
        from gateway.platform_registry import PlatformEntry

        return PlatformEntry(
            name="fakeplatform",
            label="Fake",
            adapter_factory=lambda cfg: None,
            check_fn=lambda: True,
            standalone_sender_fn=send_fn,
        )

    @pytest.mark.asyncio
    async def test_live_ntfy_adapter_receives_explicit_publish_topic(self, monkeypatch):
        from tools.send_message_tool import _send_via_adapter

        platform = Platform("ntfy")
        recorded = {}

        class Adapter:
            async def send(self, *, chat_id, content, metadata=None):
                recorded["chat_id"] = chat_id
                recorded["content"] = content
                recorded["metadata"] = metadata
                return SimpleNamespace(success=True, message_id="ntfy-id")

        runner = SimpleNamespace(adapters={platform: Adapter()})
        fake_gateway_run = ModuleType("gateway.run")
        fake_gateway_run._gateway_runner_ref = lambda: runner
        monkeypatch.setitem(sys.modules, "gateway.run", fake_gateway_run)

        result = await _send_via_adapter(
            platform,
            SimpleNamespace(extra={"publish_topic": "configured-topic"}),
            "alerts-channel",
            "done",
        )

        assert result == {"success": True, "message_id": "ntfy-id"}
        assert recorded["chat_id"] == "alerts-channel"
        assert recorded["content"] == "done"
        assert recorded["metadata"] == {"publish_topic": "alerts-channel"}

    @pytest.mark.asyncio
    async def test_standalone_sender_fn_called_when_no_adapter(self, monkeypatch):
        """Registry has hook, runner ref returns None: the hook is awaited."""
        from tools.send_message_tool import _send_via_adapter
        from gateway.platform_registry import platform_registry

        recorded = {}

        async def fake_send(pconfig, chat_id, message, **kwargs):
            recorded["pconfig"] = pconfig
            recorded["chat_id"] = chat_id
            recorded["message"] = message
            recorded["kwargs"] = kwargs
            return {"success": True, "message_id": "msg-42"}

        platform_registry.register(self._make_entry(fake_send))
        try:
            monkeypatch.setattr("gateway.run._gateway_runner_ref", lambda: None)

            pconfig = SimpleNamespace(extra={})
            result = await _send_via_adapter(
                _FakePlatform("fakeplatform"),
                pconfig,
                "room/123",
                "hello cron",
            )
        finally:
            platform_registry.unregister("fakeplatform")

        assert result == {"success": True, "message_id": "msg-42"}
        assert recorded["chat_id"] == "room/123"
        assert recorded["message"] == "hello cron"
        assert recorded["pconfig"] is pconfig

    @pytest.mark.asyncio
    async def test_standalone_sender_fn_kwargs_forwarded(self, monkeypatch):
        """thread_id, media_files, and force_document all reach the hook."""
        from tools.send_message_tool import _send_via_adapter
        from gateway.platform_registry import platform_registry

        recorded = {}

        async def fake_send(pconfig, chat_id, message, *, thread_id=None,
                            media_files=None, force_document=False):
            recorded["thread_id"] = thread_id
            recorded["media_files"] = media_files
            recorded["force_document"] = force_document
            return {"success": True, "message_id": "x"}

        platform_registry.register(self._make_entry(fake_send))
        try:
            monkeypatch.setattr("gateway.run._gateway_runner_ref", lambda: None)

            await _send_via_adapter(
                _FakePlatform("fakeplatform"),
                SimpleNamespace(extra={}),
                "chat-1",
                "hi",
                thread_id="thread-7",
                media_files=["/tmp/a.png"],
                force_document=True,
            )
        finally:
            platform_registry.unregister("fakeplatform")

        assert recorded["thread_id"] == "thread-7"
        assert recorded["media_files"] == ["/tmp/a.png"]
        assert recorded["force_document"] is True

    @pytest.mark.asyncio
    async def test_standalone_sender_fn_absent_returns_helpful_error(self, monkeypatch):
        """Registry entry has no hook: the fall-through error explains both
        options (gateway-running and standalone hook)."""
        from tools.send_message_tool import _send_via_adapter
        from gateway.platform_registry import platform_registry

        platform_registry.register(self._make_entry(None))
        try:
            monkeypatch.setattr("gateway.run._gateway_runner_ref", lambda: None)

            result = await _send_via_adapter(
                _FakePlatform("fakeplatform"),
                SimpleNamespace(extra={}),
                "chat-1",
                "hi",
            )
        finally:
            platform_registry.unregister("fakeplatform")

        assert "error" in result
        assert "fakeplatform" in result["error"]
        assert "standalone_sender_fn" in result["error"]

    @pytest.mark.asyncio
    async def test_standalone_sender_fn_raises_is_caught_and_formatted(self, monkeypatch):
        """Hook raises: error dict has 'Plugin standalone send failed: ...'"""
        from tools.send_message_tool import _send_via_adapter
        from gateway.platform_registry import platform_registry

        async def boom(pconfig, chat_id, message, **kwargs):
            raise ValueError("boom!")

        platform_registry.register(self._make_entry(boom))
        try:
            monkeypatch.setattr("gateway.run._gateway_runner_ref", lambda: None)

            result = await _send_via_adapter(
                _FakePlatform("fakeplatform"),
                SimpleNamespace(extra={}),
                "chat-1",
                "hi",
            )
        finally:
            platform_registry.unregister("fakeplatform")

        assert result == {"error": "Plugin standalone send failed: boom!"}

    @pytest.mark.asyncio
    async def test_standalone_sender_fn_return_shape_passed_through(self, monkeypatch):
        """Hook returns success dict: passed through unchanged."""
        from tools.send_message_tool import _send_via_adapter
        from gateway.platform_registry import platform_registry

        async def fake_send(pconfig, chat_id, message, **kwargs):
            return {"success": True, "message_id": "abc-123", "extra_field": "preserved"}

        platform_registry.register(self._make_entry(fake_send))
        try:
            monkeypatch.setattr("gateway.run._gateway_runner_ref", lambda: None)

            result = await _send_via_adapter(
                _FakePlatform("fakeplatform"),
                SimpleNamespace(extra={}),
                "chat-1",
                "hi",
            )
        finally:
            platform_registry.unregister("fakeplatform")

        assert result["success"] is True
        assert result["message_id"] == "abc-123"
        assert result["extra_field"] == "preserved"


# ---------------------------------------------------------------------------
# _check_send_message — availability gating
# ---------------------------------------------------------------------------

class TestCheckSendMessage:
    """The tool's check_fn governs whether the model sees ``send_message`` as
    callable for a given session. The four passing conditions are:

    1. ``HERMES_KANBAN_TASK`` is set (worker spawned by the kanban dispatcher
       — parent gateway is by definition running, but the worker's
       ``HERMES_HOME`` may be a profile dir without a ``gateway.pid``).
    2. ``HERMES_SESSION_PLATFORM`` resolves to a non-empty, non-``local`` value
       (the session is wired to a messaging platform like Telegram).
    3. ``is_gateway_running()`` returns True (CLI / orchestrator profile with
       a live gateway colocated under the same ``HERMES_HOME``).
    4. None of the above → False, tool is hidden.
    """

    def test_kanban_task_env_grants_access(self, monkeypatch):
        """Workers spawned by the dispatcher (HERMES_KANBAN_TASK set) must be
        allowed regardless of session_platform / gateway-pid state."""
        from tools.send_message_tool import _check_send_message

        monkeypatch.setenv("HERMES_KANBAN_TASK", "t_abc12345")
        monkeypatch.delenv("HERMES_SESSION_PLATFORM", raising=False)

        with patch("gateway.session_context.get_session_env", return_value=""), \
             patch("gateway.status.is_gateway_running", return_value=False):
            assert _check_send_message() is True

    def test_kanban_task_env_short_circuits_before_gateway_check(self, monkeypatch):
        """Honoring HERMES_KANBAN_TASK must not depend on importing or calling
        gateway.status — the worker may run with a HERMES_HOME that has no
        gateway.pid, and we don't want that import path to be load-bearing."""
        from tools.send_message_tool import _check_send_message

        monkeypatch.setenv("HERMES_KANBAN_TASK", "t_abc12345")

        with patch("gateway.session_context.get_session_env",
                   side_effect=AssertionError("session_context not consulted "
                                              "when HERMES_KANBAN_TASK is set")), \
             patch("gateway.status.is_gateway_running",
                   side_effect=AssertionError("gateway.status not consulted "
                                              "when HERMES_KANBAN_TASK is set")):
            assert _check_send_message() is True

    def test_messaging_platform_session_grants_access(self, monkeypatch):
        """Telegram/Discord/etc. sessions pass via the platform branch even
        without HERMES_KANBAN_TASK."""
        from tools.send_message_tool import _check_send_message

        monkeypatch.delenv("HERMES_KANBAN_TASK", raising=False)

        with patch("gateway.session_context.get_session_env", return_value="telegram"), \
             patch("gateway.status.is_gateway_running", return_value=False):
            assert _check_send_message() is True

    def test_local_platform_falls_through_to_gateway_check(self, monkeypatch):
        """``HERMES_SESSION_PLATFORM=local`` means CLI-style — must defer to
        is_gateway_running() rather than auto-grant."""
        from tools.send_message_tool import _check_send_message

        monkeypatch.delenv("HERMES_KANBAN_TASK", raising=False)

        with patch("gateway.session_context.get_session_env", return_value="local"), \
             patch("gateway.status.is_gateway_running", return_value=True) as gw_mock:
            assert _check_send_message() is True
            gw_mock.assert_called_once()

    def test_running_gateway_grants_access(self, monkeypatch):
        """Plain CLI session (no kanban task, empty platform) with a live
        gateway: tool is callable."""
        from tools.send_message_tool import _check_send_message

        monkeypatch.delenv("HERMES_KANBAN_TASK", raising=False)

        with patch("gateway.session_context.get_session_env", return_value=""), \
             patch("gateway.status.is_gateway_running", return_value=True):
            assert _check_send_message() is True

    def test_no_signals_means_unavailable(self, monkeypatch):
        """No kanban task, no platform, no gateway: tool is hidden."""
        from tools.send_message_tool import _check_send_message

        monkeypatch.delenv("HERMES_KANBAN_TASK", raising=False)

        with patch("gateway.session_context.get_session_env", return_value=""), \
             patch("gateway.status.is_gateway_running", return_value=False):
            assert _check_send_message() is False

    def test_gateway_status_import_error_is_swallowed(self, monkeypatch):
        """If gateway.status can't be imported (unusual deployment / partial
        install), the check returns False rather than raising."""
        from tools.send_message_tool import _check_send_message

        monkeypatch.delenv("HERMES_KANBAN_TASK", raising=False)

        with patch("gateway.session_context.get_session_env", return_value=""), \
             patch("gateway.status.is_gateway_running",
                   side_effect=ImportError("simulated")):
            assert _check_send_message() is False


class TestSendTelegramThreadNotFoundRetry:
    """Tests for thread-not-found retry behaviour in _send_telegram (#27012)."""

    def test_is_thread_not_found_matches_expected_errors(self):
        """_is_telegram_thread_not_found should detect thread-not-found errors."""
        class FakeError(Exception):
            pass

        assert _is_telegram_thread_not_found(FakeError("message thread not found")) is True
        assert _is_telegram_thread_not_found(FakeError("THREAD NOT FOUND")) is True
        assert _is_telegram_thread_not_found(FakeError("Bad Request: thread not found")) is True
        assert _is_telegram_thread_not_found(FakeError("chat not found")) is False
        assert _is_telegram_thread_not_found(FakeError("parse error")) is False
        assert _is_telegram_thread_not_found(FakeError("")) is False

    def test_text_send_retries_without_thread_id_on_thread_not_found(self):
        """When thread is not found, the text send should retry without
        message_thread_id."""
        call_args = []

        async def fake_retry(bot, *, chat_id, text, parse_mode, **kwargs):
            call_args.append(dict(kwargs, chat_id=chat_id, text=text))
            if len(call_args) == 1:
                raise Exception("Bad Request: message thread not found")
            return SimpleNamespace(message_id=42)

        async def run_test():
            with patch(
                "tools.send_message_tool._send_telegram_message_with_retry",
                fake_retry,
            ):
                # _send_telegram imports Bot locally; we only need to mock
                # the send path, not Bot itself (Bot import falls through
                # normally since python-telegram-bot is installed).
                return await _send_telegram(
                    "fake-token", "-100123", "hello from topic 17585",
                    thread_id="17585",
                )

        result = asyncio.run(run_test())
        assert result["success"] is True
        assert result["message_id"] == "42"
        assert len(call_args) == 2, f"expected 2 calls, got {len(call_args)}"
        # First call should have message_thread_id
        assert call_args[0].get("message_thread_id") is not None
        # Second call (retry) should NOT have message_thread_id
        assert "message_thread_id" not in call_args[1], \
            "retry should drop message_thread_id after thread-not-found"

    def test_disable_web_page_preview_not_leaked_to_media_sends(self):
        """disable_web_page_preview must never leak into a media send.

        A single captionable file + short text now rides as the document's
        caption (no separate text send), so the invariant to protect is that
        the captioned send_document does not inherit disable_web_page_preview
        (valid only for send_message).
        """
        media_kwargs_seen = []

        class FakeBot:
            async def send_message(self, **kwargs):
                return SimpleNamespace(message_id=1)

            async def send_document(self, **kwargs):
                media_kwargs_seen.append(kwargs)
                return SimpleNamespace(message_id=2)

        import tempfile
        media_path = None
        try:
            with tempfile.NamedTemporaryFile(suffix=".pdf", delete=False) as tf:
                tf.write(b"%PDF-1.4 test content")
                media_path = tf.name

            async def run_test():
                with patch("telegram.Bot", return_value=FakeBot()):
                    return await _send_telegram(
                        "fake-token", "-100123", "check preview",
                        media_files=[(media_path, False)],
                        disable_link_previews=True,
                    )

            result = asyncio.run(run_test())
            assert result["success"] is True
            # Caption rides the document bubble.
            assert media_kwargs_seen[0].get("caption") == "check preview"
            # Media send must NOT carry disable_web_page_preview.
            assert "disable_web_page_preview" not in media_kwargs_seen[0], \
                "disable_web_page_preview leaked into send_document kwargs"
        finally:
            if media_path and os.path.exists(media_path):
                os.unlink(media_path)