"""Tests for the BlueBubbles iMessage gateway adapter."""
import asyncio
import json

import pytest

from gateway.config import Platform, PlatformConfig


def _make_adapter(monkeypatch, **extra):
    monkeypatch.setenv("BLUEBUBBLES_SERVER_URL", "http://localhost:1234")
    monkeypatch.setenv("BLUEBUBBLES_PASSWORD", "secret")
    from gateway.platforms.bluebubbles import BlueBubblesAdapter

    cfg = PlatformConfig(
        enabled=True,
        extra={
            "server_url": "http://localhost:1234",
            "password": "secret",
            **extra,
        },
    )
    return BlueBubblesAdapter(cfg)


class TestBlueBubblesConfigLoading:
    def test_apply_env_overrides_bluebubbles(self, monkeypatch):
        monkeypatch.setenv("BLUEBUBBLES_SERVER_URL", "http://localhost:1234")
        monkeypatch.setenv("BLUEBUBBLES_PASSWORD", "secret")
        monkeypatch.setenv("BLUEBUBBLES_WEBHOOK_PORT", "9999")
        monkeypatch.setenv("BLUEBUBBLES_REQUIRE_MENTION", "true")
        monkeypatch.setenv("BLUEBUBBLES_MENTION_PATTERNS", r'["(?i)^amos\\b"]')
        from gateway.config import GatewayConfig, _apply_env_overrides

        config = GatewayConfig()
        _apply_env_overrides(config)
        assert Platform.BLUEBUBBLES in config.platforms
        bc = config.platforms[Platform.BLUEBUBBLES]
        assert bc.enabled is True
        assert bc.extra["server_url"] == "http://localhost:1234"
        assert bc.extra["password"] == "secret"
        assert bc.extra["webhook_port"] == 9999
        assert bc.extra["require_mention"] is True
        assert bc.extra["mention_patterns"] == ["(?i)^amos\\b"]

    def test_home_channel_set_from_env(self, monkeypatch):
        monkeypatch.setenv("BLUEBUBBLES_SERVER_URL", "http://localhost:1234")
        monkeypatch.setenv("BLUEBUBBLES_PASSWORD", "secret")
        monkeypatch.setenv("BLUEBUBBLES_HOME_CHANNEL", "user@example.com")
        from gateway.config import GatewayConfig, _apply_env_overrides

        config = GatewayConfig()
        _apply_env_overrides(config)
        hc = config.platforms[Platform.BLUEBUBBLES].home_channel
        assert hc is not None
        assert hc.chat_id == "user@example.com"

    def test_not_connected_without_password(self, monkeypatch):
        monkeypatch.setenv("BLUEBUBBLES_SERVER_URL", "http://localhost:1234")
        monkeypatch.delenv("BLUEBUBBLES_PASSWORD", raising=False)
        from gateway.config import GatewayConfig, _apply_env_overrides

        config = GatewayConfig()
        _apply_env_overrides(config)
        assert Platform.BLUEBUBBLES not in config.get_connected_platforms()


class TestBlueBubblesHelpers:
    def test_check_requirements(self, monkeypatch):
        monkeypatch.setenv("BLUEBUBBLES_SERVER_URL", "http://localhost:1234")
        monkeypatch.setenv("BLUEBUBBLES_PASSWORD", "secret")
        from gateway.platforms.bluebubbles import check_bluebubbles_requirements

        assert check_bluebubbles_requirements() is True

    def test_supports_message_editing_is_false(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        assert adapter.SUPPORTS_MESSAGE_EDITING is False

    def test_truncate_message_omits_pagination_suffixes(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        chunks = adapter.truncate_message("abcdefghij", max_length=6)
        assert len(chunks) > 1
        assert "".join(chunks) == "abcdefghij"
        assert all("(" not in chunk for chunk in chunks)

    @pytest.mark.asyncio
    async def test_send_splits_paragraphs_into_multiple_bubbles(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        sent = []

        async def fake_resolve_chat_guid(chat_id):
            return "iMessage;-;user@example.com"

        async def fake_api_post(path, payload):
            sent.append(payload["message"])
            return {"data": {"guid": f"msg-{len(sent)}"}}

        monkeypatch.setattr(adapter, "_resolve_chat_guid", fake_resolve_chat_guid)
        monkeypatch.setattr(adapter, "_api_post", fake_api_post)

        result = await adapter.send("user@example.com", "first thought\n\nsecond thought")

        assert result.success is True
        assert sent == ["first thought", "second thought"]

    def test_format_message_strips_markdown(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        assert adapter.format_message("**Hello** `world`") == "Hello world"

    def test_format_message_preserves_underscores_in_identifiers(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        text = "Use /api_v2 with FEATURE_FLAG_NAME and config_file.json"
        assert adapter.format_message(text) == text

    def test_strip_markdown_headers(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        assert adapter.format_message("## Heading\ntext") == "Heading\ntext"

    def test_strip_markdown_links(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        assert adapter.format_message("[click here](http://example.com)") == "click here"

    def test_init_normalizes_webhook_path(self, monkeypatch):
        adapter = _make_adapter(monkeypatch, webhook_path="bluebubbles-webhook")
        assert adapter.webhook_path == "/bluebubbles-webhook"

    def test_init_preserves_leading_slash(self, monkeypatch):
        adapter = _make_adapter(monkeypatch, webhook_path="/my-hook")
        assert adapter.webhook_path == "/my-hook"

    def test_server_url_normalized(self, monkeypatch):
        adapter = _make_adapter(monkeypatch, server_url="http://localhost:1234/")
        assert adapter.server_url == "http://localhost:1234"

    def test_server_url_adds_scheme(self, monkeypatch):
        adapter = _make_adapter(monkeypatch, server_url="localhost:1234")
        assert adapter.server_url == "http://localhost:1234"

    def test_default_mention_patterns_match_hermes_variants(self, monkeypatch):
        adapter = _make_adapter(monkeypatch, require_mention=True)

        assert adapter.require_mention is True
        assert adapter._message_matches_mention_patterns("Hermes, summarize this")
        assert adapter._message_matches_mention_patterns("@Hermes agent help")
        assert not adapter._message_matches_mention_patterns("casual family chatter")
        assert not adapter._message_matches_mention_patterns("antihermes should not match")

    def test_custom_mention_patterns_override_defaults(self, monkeypatch):
        adapter = _make_adapter(
            monkeypatch,
            require_mention=True,
            mention_patterns=[r"(?<![\w@])@?amos\b[,:\-]?"],
        )

        assert adapter._message_matches_mention_patterns("Amos what is next?")
        assert not adapter._message_matches_mention_patterns("Hermes what is next?")

    def test_clean_mention_text_strips_leading_wake_word(self, monkeypatch):
        adapter = _make_adapter(monkeypatch, require_mention=True)

        assert adapter._clean_mention_text("Hermes, summarize this") == "summarize this"
        assert adapter._clean_mention_text("Hermes agent: summarize this") == "summarize this"
        assert adapter._clean_mention_text("please ask Hermes about this") == "please ask Hermes about this"


class _FakeBlueBubblesRequest:
    def __init__(self, payload, password="secret"):
        self.query = {"password": password}
        self.headers = {}
        self._body = json.dumps(payload).encode("utf-8")

    async def read(self):
        return self._body


class TestBlueBubblesMentionGating:
    @pytest.mark.asyncio
    async def test_group_message_without_mention_is_acknowledged_and_skipped(self, monkeypatch):
        adapter = _make_adapter(
            monkeypatch,
            require_mention=True,
            send_read_receipts=False,
        )
        handled = []

        async def fake_handle_message(event):
            handled.append(event)

        monkeypatch.setattr(adapter, "handle_message", fake_handle_message)
        response = await adapter._handle_webhook(_FakeBlueBubblesRequest({
            "type": "new-message",
            "data": {
                "guid": "msg-1",
                "text": "casual family chatter",
                "handle": {"address": "+15555550100"},
                "isFromMe": False,
                "isGroup": True,
                "chats": [{"guid": "iMessage;+;group-chat"}],
            },
        }))
        await asyncio.sleep(0)

        assert response.status == 200
        assert handled == []

    @pytest.mark.asyncio
    async def test_group_message_with_default_mention_is_dispatched_cleaned(self, monkeypatch):
        adapter = _make_adapter(
            monkeypatch,
            require_mention=True,
            send_read_receipts=False,
        )
        handled = []

        async def fake_handle_message(event):
            handled.append(event)

        monkeypatch.setattr(adapter, "handle_message", fake_handle_message)
        response = await adapter._handle_webhook(_FakeBlueBubblesRequest({
            "type": "new-message",
            "data": {
                "guid": "msg-2",
                "text": "Hermes, summarize this",
                "handle": {"address": "+15555550100"},
                "isFromMe": False,
                "isGroup": True,
                "chats": [{"guid": "iMessage;+;group-chat"}],
            },
        }))
        await asyncio.sleep(0)

        assert response.status == 200
        assert [event.text for event in handled] == ["summarize this"]

    @pytest.mark.asyncio
    async def test_dm_message_does_not_require_mention(self, monkeypatch):
        adapter = _make_adapter(
            monkeypatch,
            require_mention=True,
            send_read_receipts=False,
        )
        handled = []

        async def fake_handle_message(event):
            handled.append(event)

        monkeypatch.setattr(adapter, "handle_message", fake_handle_message)
        response = await adapter._handle_webhook(_FakeBlueBubblesRequest({
            "type": "new-message",
            "data": {
                "guid": "msg-3",
                "text": "hello from a dm",
                "handle": {"address": "user@example.com"},
                "isFromMe": False,
                "chatGuid": "iMessage;-;user@example.com",
                "chatIdentifier": "user@example.com",
            },
        }))
        await asyncio.sleep(0)

        assert response.status == 200
        assert [event.text for event in handled] == ["hello from a dm"]


class TestBlueBubblesWebhookParsing:
    def test_webhook_prefers_chat_guid_over_message_guid(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        payload = {
            "guid": "MESSAGE-GUID",
            "chatGuid": "iMessage;-;user@example.com",
            "chatIdentifier": "user@example.com",
        }
        record = adapter._extract_payload_record(payload) or {}
        chat_guid = adapter._value(
            record.get("chatGuid"),
            payload.get("chatGuid"),
            record.get("chat_guid"),
            payload.get("chat_guid"),
            payload.get("guid"),
        )
        assert chat_guid == "iMessage;-;user@example.com"

    def test_webhook_can_fall_back_to_sender_when_chat_fields_missing(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        payload = {
            "data": {
                "guid": "MESSAGE-GUID",
                "text": "hello",
                "handle": {"address": "user@example.com"},
                "isFromMe": False,
            }
        }
        record = adapter._extract_payload_record(payload) or {}
        chat_guid = adapter._value(
            record.get("chatGuid"),
            payload.get("chatGuid"),
            record.get("chat_guid"),
            payload.get("chat_guid"),
            payload.get("guid"),
        )
        chat_identifier = adapter._value(
            record.get("chatIdentifier"),
            record.get("identifier"),
            payload.get("chatIdentifier"),
            payload.get("identifier"),
        )
        sender = (
            adapter._value(
                record.get("handle", {}).get("address")
                if isinstance(record.get("handle"), dict)
                else None,
                record.get("sender"),
                record.get("from"),
                record.get("address"),
            )
            or chat_identifier
            or chat_guid
        )
        if not (chat_guid or chat_identifier) and sender:
            chat_identifier = sender
        assert chat_identifier == "user@example.com"

    def test_webhook_extracts_chat_guid_from_chats_array_dm(self, monkeypatch):
        """BB v1.9+ webhook payloads omit top-level chatGuid; GUID is in chats[0].guid."""
        adapter = _make_adapter(monkeypatch)
        payload = {
            "type": "new-message",
            "data": {
                "guid": "MESSAGE-GUID",
                "text": "hello",
                "handle": {"address": "+15551234567"},
                "isFromMe": False,
                "chats": [
                    {"guid": "any;-;+15551234567", "chatIdentifier": "+15551234567"}
                ],
            },
        }
        record = adapter._extract_payload_record(payload) or {}
        chat_guid = adapter._value(
            record.get("chatGuid"),
            payload.get("chatGuid"),
            record.get("chat_guid"),
            payload.get("chat_guid"),
            payload.get("guid"),
        )
        if not chat_guid:
            _chats = record.get("chats") or []
            if _chats and isinstance(_chats[0], dict):
                chat_guid = _chats[0].get("guid") or _chats[0].get("chatGuid")
        assert chat_guid == "any;-;+15551234567"

    def test_webhook_extracts_chat_guid_from_chats_array_group(self, monkeypatch):
        """Group chat GUIDs contain ;+; and must be extracted from chats array."""
        adapter = _make_adapter(monkeypatch)
        payload = {
            "type": "new-message",
            "data": {
                "guid": "MESSAGE-GUID",
                "text": "hello everyone",
                "handle": {"address": "+15551234567"},
                "isFromMe": False,
                "isGroup": True,
                "chats": [{"guid": "any;+;chat-uuid-abc123"}],
            },
        }
        record = adapter._extract_payload_record(payload) or {}
        chat_guid = adapter._value(
            record.get("chatGuid"),
            payload.get("chatGuid"),
            record.get("chat_guid"),
            payload.get("chat_guid"),
            payload.get("guid"),
        )
        if not chat_guid:
            _chats = record.get("chats") or []
            if _chats and isinstance(_chats[0], dict):
                chat_guid = _chats[0].get("guid") or _chats[0].get("chatGuid")
        assert chat_guid == "any;+;chat-uuid-abc123"

    def test_extract_payload_record_accepts_list_data(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        payload = {
            "type": "new-message",
            "data": [
                {
                    "text": "hello",
                    "chatGuid": "iMessage;-;user@example.com",
                    "chatIdentifier": "user@example.com",
                }
            ],
        }
        record = adapter._extract_payload_record(payload)
        assert record == payload["data"][0]

    def test_extract_payload_record_dict_data(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        payload = {"data": {"text": "hello", "chatGuid": "iMessage;-;+1234"}}
        record = adapter._extract_payload_record(payload)
        assert record["text"] == "hello"

    def test_extract_payload_record_fallback_to_message(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        payload = {"message": {"text": "hello"}}
        record = adapter._extract_payload_record(payload)
        assert record["text"] == "hello"


class TestBlueBubblesGuidResolution:
    def test_raw_guid_returned_as_is(self, monkeypatch):
        """If target already contains ';' it's a raw GUID — return unchanged."""
        adapter = _make_adapter(monkeypatch)
        import asyncio

        result = asyncio.get_event_loop().run_until_complete(
            adapter._resolve_chat_guid("iMessage;-;user@example.com")
        )
        assert result == "iMessage;-;user@example.com"

    def test_empty_target_returns_none(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        import asyncio

        result = asyncio.get_event_loop().run_until_complete(
            adapter._resolve_chat_guid("")
        )
        assert result is None


class TestBlueBubblesAttachmentDownload:
    """Verify _download_attachment routes to the correct cache helper."""

    def test_download_image_uses_image_cache(self, monkeypatch):
        """Image MIME routes to cache_image_from_bytes."""
        adapter = _make_adapter(monkeypatch)
        import asyncio

        # Mock the HTTP client response
        class MockResponse:
            status_code = 200
            content = b"\x89PNG\r\n\x1a\n"

            def raise_for_status(self):
                pass

        async def mock_get(*args, **kwargs):
            return MockResponse()

        adapter.client = type("MockClient", (), {"get": mock_get})()

        cached_path = None

        def mock_cache_image(data, ext):
            nonlocal cached_path
            cached_path = f"/tmp/test_image{ext}"
            return cached_path

        monkeypatch.setattr(
            "gateway.platforms.bluebubbles.cache_image_from_bytes",
            mock_cache_image,
        )

        att_meta = {"mimeType": "image/png", "transferName": "photo.png"}
        result = asyncio.get_event_loop().run_until_complete(
            adapter._download_attachment("att-guid-123", att_meta)
        )
        assert result == "/tmp/test_image.png"

    def test_download_audio_uses_audio_cache(self, monkeypatch):
        """Audio MIME routes to cache_audio_from_bytes."""
        adapter = _make_adapter(monkeypatch)
        import asyncio

        class MockResponse:
            status_code = 200
            content = b"fake-audio-data"

            def raise_for_status(self):
                pass

        async def mock_get(*args, **kwargs):
            return MockResponse()

        adapter.client = type("MockClient", (), {"get": mock_get})()

        cached_path = None

        def mock_cache_audio(data, ext):
            nonlocal cached_path
            cached_path = f"/tmp/test_audio{ext}"
            return cached_path

        monkeypatch.setattr(
            "gateway.platforms.bluebubbles.cache_audio_from_bytes",
            mock_cache_audio,
        )

        att_meta = {"mimeType": "audio/mpeg", "transferName": "voice.mp3"}
        result = asyncio.get_event_loop().run_until_complete(
            adapter._download_attachment("att-guid-456", att_meta)
        )
        assert result == "/tmp/test_audio.mp3"

    def test_download_document_uses_document_cache(self, monkeypatch):
        """Non-image/audio MIME routes to cache_document_from_bytes."""
        adapter = _make_adapter(monkeypatch)
        import asyncio

        class MockResponse:
            status_code = 200
            content = b"fake-doc-data"

            def raise_for_status(self):
                pass

        async def mock_get(*args, **kwargs):
            return MockResponse()

        adapter.client = type("MockClient", (), {"get": mock_get})()

        cached_path = None

        def mock_cache_doc(data, filename):
            nonlocal cached_path
            cached_path = f"/tmp/{filename}"
            return cached_path

        monkeypatch.setattr(
            "gateway.platforms.bluebubbles.cache_document_from_bytes",
            mock_cache_doc,
        )

        att_meta = {"mimeType": "application/pdf", "transferName": "report.pdf"}
        result = asyncio.get_event_loop().run_until_complete(
            adapter._download_attachment("att-guid-789", att_meta)
        )
        assert result == "/tmp/report.pdf"

    def test_download_returns_none_without_client(self, monkeypatch):
        """No client → returns None gracefully."""
        adapter = _make_adapter(monkeypatch)
        adapter.client = None
        import asyncio

        result = asyncio.get_event_loop().run_until_complete(
            adapter._download_attachment("att-guid", {"mimeType": "image/png"})
        )
        assert result is None


# ---------------------------------------------------------------------------
# Webhook registration
# ---------------------------------------------------------------------------


class TestBlueBubblesWebhookUrl:
    """_webhook_url property normalises local hosts to 'localhost'."""

    def test_default_host(self, monkeypatch):
        adapter = _make_adapter(monkeypatch)
        # Default webhook_host is 0.0.0.0 → normalized to localhost
        assert "localhost" in adapter._webhook_url
        assert str(adapter.webhook_port) in adapter._webhook_url
        assert adapter.webhook_path in adapter._webhook_url

    @pytest.mark.parametrize("host", ["0.0.0.0", "127.0.0.1", "localhost", "::"])
    def test_local_hosts_normalized(self, monkeypatch, host):
        adapter = _make_adapter(monkeypatch, webhook_host=host)
        assert adapter._webhook_url.startswith("http://localhost:")

    def test_custom_host_preserved(self, monkeypatch):
        adapter = _make_adapter(monkeypatch, webhook_host="192.168.1.50")
        assert "192.168.1.50" in adapter._webhook_url

    def test_register_url_embeds_password(self, monkeypatch):
        """_webhook_register_url should append ?password=... for inbound auth."""
        adapter = _make_adapter(monkeypatch, password="secret123")
        assert adapter._webhook_register_url.endswith("?password=secret123")
        assert adapter._webhook_register_url.startswith(adapter._webhook_url)

    def test_register_url_url_encodes_password(self, monkeypatch):
        """Passwords with special characters must be URL-encoded."""
        adapter = _make_adapter(monkeypatch, password="W9fTC&L5JL*@")
        assert "password=W9fTC%26L5JL%2A%40" in adapter._webhook_register_url

    def test_register_url_for_log_masks_password(self, monkeypatch):
        """Log-safe webhook URLs must never expose the webhook password."""
        adapter = _make_adapter(monkeypatch, password="W9fTC&L5JL*@")
        safe_url = adapter._webhook_register_url_for_log
        assert safe_url.endswith("?password=***")
        assert "W9fTC" not in safe_url
        assert "%26" not in safe_url

    def test_register_url_omits_query_when_no_password(self, monkeypatch):
        """If no password is configured, the register URL should be the bare URL."""
        monkeypatch.delenv("BLUEBUBBLES_PASSWORD", raising=False)
        from gateway.platforms.bluebubbles import BlueBubblesAdapter
        cfg = PlatformConfig(
            enabled=True,
            extra={"server_url": "http://localhost:1234", "password": ""},
        )
        adapter = BlueBubblesAdapter(cfg)
        assert adapter._webhook_register_url == adapter._webhook_url


class TestBlueBubblesWebhookRegistration:
    """Tests for _register_webhook, _unregister_webhook, _find_registered_webhooks."""

    @staticmethod
    def _mock_client(get_response=None, post_response=None, delete_ok=True):
        """Build a tiny mock httpx.AsyncClient."""

        async def mock_get(*args, **kwargs):
            class R:
                status_code = 200
                def raise_for_status(self):
                    pass
                def json(self):
                    return get_response or {"status": 200, "data": []}
            return R()

        async def mock_post(*args, **kwargs):
            class R:
                status_code = 200
                def raise_for_status(self):
                    pass
                def json(self):
                    return post_response or {"status": 200, "data": {}}
            return R()

        async def mock_delete(*args, **kwargs):
            class R:
                status_code = 200 if delete_ok else 500
                def raise_for_status(self_inner):
                    if not delete_ok:
                        raise Exception("delete failed")
            return R()

        return type(
            "MockClient", (),
            {"get": mock_get, "post": mock_post, "delete": mock_delete},
        )()

    # -- _find_registered_webhooks --

    def test_find_registered_webhooks_returns_matches(self, monkeypatch):
        import asyncio
        adapter = _make_adapter(monkeypatch)
        url = adapter._webhook_url
        adapter.client = self._mock_client(
            get_response={"status": 200, "data": [
                {"id": 1, "url": url, "events": ["new-message"]},
                {"id": 2, "url": "http://other:9999/hook", "events": ["message"]},
            ]}
        )
        result = asyncio.get_event_loop().run_until_complete(
            adapter._find_registered_webhooks(url)
        )
        assert len(result) == 1
        assert result[0]["id"] == 1

    def test_find_registered_webhooks_empty_when_none(self, monkeypatch):
        import asyncio
        adapter = _make_adapter(monkeypatch)
        adapter.client = self._mock_client(
            get_response={"status": 200, "data": []}
        )
        result = asyncio.get_event_loop().run_until_complete(
            adapter._find_registered_webhooks(adapter._webhook_url)
        )
        assert result == []

    def test_find_registered_webhooks_handles_api_error(self, monkeypatch):
        import asyncio
        adapter = _make_adapter(monkeypatch)
        adapter.client = self._mock_client()

        # Override _api_get to raise
        async def bad_get(path):
            raise ConnectionError("server down")
        adapter._api_get = bad_get

        result = asyncio.get_event_loop().run_until_complete(
            adapter._find_registered_webhooks(adapter._webhook_url)
        )
        assert result == []

    # -- _register_webhook --

    def test_register_fresh(self, monkeypatch):
        """No existing webhook → POST creates one."""
        import asyncio
        adapter = _make_adapter(monkeypatch)
        adapter.client = self._mock_client(
            get_response={"status": 200, "data": []},
            post_response={"status": 200, "data": {"id": 42}},
        )
        ok = asyncio.get_event_loop().run_until_complete(
            adapter._register_webhook()
        )
        assert ok is True

    def test_register_accepts_201(self, monkeypatch):
        """BB might return 201 Created — must still succeed."""
        import asyncio
        adapter = _make_adapter(monkeypatch)
        adapter.client = self._mock_client(
            get_response={"status": 200, "data": []},
            post_response={"status": 201, "data": {"id": 43}},
        )
        ok = asyncio.get_event_loop().run_until_complete(
            adapter._register_webhook()
        )
        assert ok is True

    def test_register_reuses_existing(self, monkeypatch):
        """Crash resilience — existing registration is reused, no POST needed."""
        import asyncio
        adapter = _make_adapter(monkeypatch)
        url = adapter._webhook_register_url
        adapter.client = self._mock_client(
            get_response={"status": 200, "data": [
                {"id": 7, "url": url, "events": ["new-message"]},
            ]},
        )

        # Track whether POST was called
        post_called = False
        orig_api_post = adapter._api_post
        async def tracking_post(path, payload):
            nonlocal post_called
            post_called = True
            return await orig_api_post(path, payload)
        adapter._api_post = tracking_post

        ok = asyncio.get_event_loop().run_until_complete(
            adapter._register_webhook()
        )
        assert ok is True
        assert not post_called, "Should reuse existing, not POST again"

    def test_register_returns_false_without_client(self, monkeypatch):
        import asyncio
        adapter = _make_adapter(monkeypatch)
        adapter.client = None
        ok = asyncio.get_event_loop().run_until_complete(
            adapter._register_webhook()
        )
        assert ok is False

    def test_register_returns_false_on_server_error(self, monkeypatch):
        import asyncio
        adapter = _make_adapter(monkeypatch)
        adapter.client = self._mock_client(
            get_response={"status": 200, "data": []},
            post_response={"status": 500, "message": "internal error"},
        )
        ok = asyncio.get_event_loop().run_until_complete(
            adapter._register_webhook()
        )
        assert ok is False

    # -- _unregister_webhook --

    def test_unregister_removes_matching(self, monkeypatch):
        import asyncio
        adapter = _make_adapter(monkeypatch)
        url = adapter._webhook_register_url
        adapter.client = self._mock_client(
            get_response={"status": 200, "data": [
                {"id": 10, "url": url},
            ]},
        )
        ok = asyncio.get_event_loop().run_until_complete(
            adapter._unregister_webhook()
        )
        assert ok is True

    def test_unregister_removes_all_duplicates(self, monkeypatch):
        """Multiple orphaned registrations for same URL — all get removed."""
        import asyncio
        adapter = _make_adapter(monkeypatch)
        url = adapter._webhook_register_url
        deleted_ids = []

        async def mock_delete(*args, **kwargs):
            # Extract ID from URL
            url_str = args[0] if args else ""
            deleted_ids.append(url_str)
            class R:
                status_code = 200
                def raise_for_status(self):
                    pass
            return R()

        adapter.client = self._mock_client(
            get_response={"status": 200, "data": [
                {"id": 1, "url": url},
                {"id": 2, "url": url},
                {"id": 3, "url": "http://other/hook"},
            ]},
        )
        adapter.client.delete = mock_delete

        ok = asyncio.get_event_loop().run_until_complete(
            adapter._unregister_webhook()
        )
        assert ok is True
        assert len(deleted_ids) == 2

    def test_unregister_returns_false_without_client(self, monkeypatch):
        import asyncio
        adapter = _make_adapter(monkeypatch)
        adapter.client = None
        ok = asyncio.get_event_loop().run_until_complete(
            adapter._unregister_webhook()
        )
        assert ok is False

    def test_unregister_handles_api_failure_gracefully(self, monkeypatch):
        import asyncio
        adapter = _make_adapter(monkeypatch)
        adapter.client = self._mock_client()

        async def bad_get(path):
            raise ConnectionError("server down")
        adapter._api_get = bad_get

        ok = asyncio.get_event_loop().run_until_complete(
            adapter._unregister_webhook()
        )
        assert ok is False