fix(slack): honor NO_PROXY for Slack transport

gateway/platforms/base.py

@@ -336,6 +336,39 @@ def proxy_kwargs_for_aiohttp(proxy_url: str | None) -> tuple[dict, dict]:
     return {}, {"proxy": proxy_url}
 
 
+def is_host_excluded_by_no_proxy(hostname: str, no_proxy_value: str | None = None) -> bool:
+    """Return True when ``hostname`` matches a ``NO_PROXY`` entry.
+
+    Supports comma- or whitespace-separated entries with optional leading dots
+    and ``*.`` wildcards, which match both the apex domain and subdomains.
+    """
+    raw = no_proxy_value
+    if raw is None:
+        raw = os.environ.get("NO_PROXY") or os.environ.get("no_proxy") or ""
+
+    raw = raw.strip()
+    if not raw:
+        return False
+
+    lower_hostname = hostname.lower()
+    for entry in re.split(r"[\s,]+", raw):
+        normalized = entry.strip().lower()
+        if not normalized:
+            continue
+        if normalized == "*":
+            return True
+
+        if normalized.startswith("*."):
+            normalized = normalized[2:]
+        elif normalized.startswith("."):
+            normalized = normalized[1:]
+
+        if lower_hostname == normalized or lower_hostname.endswith(f".{normalized}"):
+            return True
+
+    return False
+
+
 from dataclasses import dataclass, field
 from datetime import datetime
 from pathlib import Path

gateway/platforms/slack.py

@@ -41,6 +41,8 @@ from gateway.platforms.base import (
     ProcessingOutcome,
     SendResult,
     SUPPORTED_DOCUMENT_TYPES,
+    is_host_excluded_by_no_proxy,
+    resolve_proxy_url,
     safe_url_for_log,
     cache_document_from_bytes,
 )
@@ -217,6 +219,40 @@ def _serialize_slack_blocks_for_agent(blocks: list, max_chars: int = 6000) -> st
     return f"[Slack Block Kit payload for this message]\n```json\n{payload}\n```"
 
 
+def _apply_slack_proxy(client: Any, proxy_url: Optional[str]) -> None:
+    """Apply a resolved proxy to a Slack SDK client or clear it explicitly."""
+    if hasattr(client, "proxy"):
+        client.proxy = proxy_url
+
+
+_SLACK_PROXY_HOSTS = (
+    "slack.com",
+    "files.slack.com",
+    "wss-primary.slack.com",
+)
+
+
+def _resolve_slack_proxy_url() -> Optional[str]:
+    """Resolve a proxy URL that Slack SDK clients can safely use."""
+    proxy_url = resolve_proxy_url()
+    if not proxy_url:
+        return None
+
+    normalized = proxy_url.lower()
+    if not normalized.startswith(("http://", "https://")):
+        logger.info(
+            "[Slack] Ignoring unsupported proxy scheme for Slack transport: %s",
+            safe_url_for_log(proxy_url),
+        )
+        return None
+
+    if any(is_host_excluded_by_no_proxy(host) for host in _SLACK_PROXY_HOSTS):
+        logger.info("[Slack] NO_PROXY bypasses Slack proxy configuration")
+        return None
+
+    return proxy_url
+
+
 class SlackAdapter(BasePlatformAdapter):
     """
     Slack bot adapter using Socket Mode.
@@ -237,13 +273,13 @@ class SlackAdapter(BasePlatformAdapter):
 
     def __init__(self, config: PlatformConfig):
         super().__init__(config, Platform.SLACK)
-        self._app: Optional[AsyncApp] = None
+        self._app: Optional[Any] = None
-        self._handler: Optional[AsyncSocketModeHandler] = None
+        self._handler: Optional[Any] = None
         self._bot_user_id: Optional[str] = None
         self._user_name_cache: Dict[str, str] = {}  # user_id → display name
         self._socket_mode_task: Optional[asyncio.Task] = None
         # Multi-workspace support
-        self._team_clients: Dict[str, AsyncWebClient] = {}   # team_id → WebClient
+        self._team_clients: Dict[str, Any] = {}   # team_id → WebClient
         self._team_bot_user_ids: Dict[str, str] = {}          # team_id → bot_user_id
         self._channel_team: Dict[str, str] = {}                # channel_id → team_id
         # Dedup cache: prevents duplicate bot responses when Socket Mode
@@ -350,6 +386,10 @@ class SlackAdapter(BasePlatformAdapter):
             logger.error("[Slack] SLACK_APP_TOKEN not set")
             return False
 
+        proxy_url = _resolve_slack_proxy_url()
+        if proxy_url:
+            logger.info("[Slack] Using proxy for Slack transport: %s", safe_url_for_log(proxy_url))
+
         # Support comma-separated bot tokens for multi-workspace
         bot_tokens = [t.strip() for t in raw_token.split(",") if t.strip()]
 
@@ -377,10 +417,12 @@ class SlackAdapter(BasePlatformAdapter):
             # First token is the primary — used for AsyncApp / Socket Mode
             primary_token = bot_tokens[0]
             self._app = AsyncApp(token=primary_token)
+            _apply_slack_proxy(self._app.client, proxy_url)
 
             # Register each bot token and map team_id → client
             for token in bot_tokens:
                 client = AsyncWebClient(token=token)
+                _apply_slack_proxy(client, proxy_url)
                 auth_response = await client.auth_test()
                 team_id = auth_response.get("team_id", "")
                 bot_user_id = auth_response.get("user_id", "")
@@ -473,7 +515,8 @@ class SlackAdapter(BasePlatformAdapter):
                 self._app.action(_action_id)(self._handle_approval_action)
 
             # Start Socket Mode handler in background
-            self._handler = AsyncSocketModeHandler(self._app, app_token)
+            self._handler = AsyncSocketModeHandler(self._app, app_token, proxy=proxy_url)
+            _apply_slack_proxy(self._handler.client, proxy_url)
             self._socket_mode_task = asyncio.create_task(self._handler.start_async())
 
             self._running = True
@@ -503,7 +546,7 @@ class SlackAdapter(BasePlatformAdapter):
 
         logger.info("[Slack] Disconnected")
 
-    def _get_client(self, chat_id: str) -> AsyncWebClient:
+    def _get_client(self, chat_id: str) -> Any:
         """Return the workspace-specific WebClient for a channel."""
         team_id = self._channel_team.get(chat_id)
         if team_id and team_id in self._team_clients:

tests/gateway/test_slack.py

@@ -11,7 +11,7 @@ We mock the slack modules at import time to avoid collection errors.
 import asyncio
 import os
 import sys
-from unittest.mock import AsyncMock, MagicMock, patch
+from unittest.mock import AsyncMock, MagicMock, patch, call
 
 import pytest
 
@@ -21,6 +21,7 @@ from gateway.platforms.base import (
     MessageType,
     SendResult,
     SUPPORTED_DOCUMENT_TYPES,
+    is_host_excluded_by_no_proxy,
 )
 
 
@@ -188,6 +189,198 @@ class TestSlackConnectCleanup:
         assert adapter._platform_lock_identity is None
 
 
+# ---------------------------------------------------------------------------
+# TestSlackProxyBehavior
+# ---------------------------------------------------------------------------
+
+class TestSlackProxyBehavior:
+    def test_no_proxy_helper_matches_slack_hosts(self):
+        assert is_host_excluded_by_no_proxy("slack.com", "localhost,.slack.com")
+        assert is_host_excluded_by_no_proxy("files.slack.com", "localhost slack.com")
+        assert is_host_excluded_by_no_proxy("wss-primary.slack.com", "*")
+        assert not is_host_excluded_by_no_proxy("slack.com", "localhost,.internal.corp")
+
+    def test_resolve_slack_proxy_url_ignores_unsupported_proxy_schemes(self):
+        with patch.object(_slack_mod, "resolve_proxy_url", return_value="socks5://proxy.example.com:1080"):
+            assert _slack_mod._resolve_slack_proxy_url() is None
+
+    def test_resolve_slack_proxy_url_checks_all_slack_hosts(self):
+        with patch.object(_slack_mod, "resolve_proxy_url", return_value="http://proxy.example.com:3128"), \
+             patch.object(_slack_mod, "is_host_excluded_by_no_proxy", side_effect=lambda host: host == "wss-primary.slack.com") as excluded:
+            assert _slack_mod._resolve_slack_proxy_url() is None
+            excluded.assert_has_calls([
+                call("slack.com"),
+                call("files.slack.com"),
+                call("wss-primary.slack.com"),
+            ])
+
+    @pytest.mark.asyncio
+    async def test_connect_uses_proxy_when_not_bypassed(self):
+        created_apps = []
+        created_clients = []
+
+        class FakeWebClient:
+            def __init__(self, token):
+                self.token = token
+                self.proxy = "constructor-default"
+                suffix = token.split("-")[-1]
+                self.auth_test = AsyncMock(return_value={
+                    "team_id": f"T_{suffix}",
+                    "user_id": f"U_{suffix}",
+                    "user": f"bot-{suffix}",
+                    "team": f"Team {suffix}",
+                })
+                created_clients.append(self)
+
+        class FakeApp:
+            def __init__(self, token):
+                self.token = token
+                self.client = FakeWebClient(token)
+                self.registered_events = []
+                self.registered_commands = []
+                self.registered_actions = []
+                created_apps.append(self)
+
+            def event(self, event_type):
+                self.registered_events.append(event_type)
+
+                def decorator(fn):
+                    return fn
+
+                return decorator
+
+            def command(self, command_name):
+                self.registered_commands.append(command_name)
+
+                def decorator(fn):
+                    return fn
+
+                return decorator
+
+            def action(self, action_id):
+                self.registered_actions.append(action_id)
+
+                def decorator(fn):
+                    return fn
+
+                return decorator
+
+        class FakeSocketModeHandler:
+            def __init__(self, app, app_token, proxy=None):
+                self.app = app
+                self.app_token = app_token
+                self.proxy = proxy
+                self.client = MagicMock(proxy="constructor-default")
+
+            def start_async(self):
+                return None
+
+            async def close_async(self):
+                return None
+
+        config = PlatformConfig(enabled=True, token="xoxb-primary,xoxb-secondary")
+        adapter = SlackAdapter(config)
+
+        with patch.object(_slack_mod, "AsyncApp", side_effect=FakeApp), \
+             patch.object(_slack_mod, "AsyncWebClient", side_effect=FakeWebClient), \
+             patch.object(_slack_mod, "AsyncSocketModeHandler", FakeSocketModeHandler), \
+             patch.object(_slack_mod, "_resolve_slack_proxy_url", return_value="http://proxy.example.com:3128"), \
+             patch.dict(os.environ, {"SLACK_APP_TOKEN": "xapp-fake"}, clear=False), \
+             patch("gateway.status.acquire_scoped_lock", return_value=(True, None)), \
+             patch("asyncio.create_task", return_value=MagicMock(name="socket-mode-task")):
+            result = await adapter.connect()
+
+        assert result is True
+        assert created_apps[0].client.proxy == "http://proxy.example.com:3128"
+        assert all(client.proxy == "http://proxy.example.com:3128" for client in created_clients)
+        assert adapter._handler is not None
+        assert adapter._handler.proxy == "http://proxy.example.com:3128"
+        assert adapter._handler.client.proxy == "http://proxy.example.com:3128"
+
+    @pytest.mark.asyncio
+    async def test_connect_clears_proxy_when_no_proxy_matches_slack(self):
+        created_apps = []
+        created_clients = []
+
+        class FakeWebClient:
+            def __init__(self, token):
+                self.token = token
+                self.proxy = "constructor-default"
+                suffix = token.split("-")[-1]
+                self.auth_test = AsyncMock(return_value={
+                    "team_id": f"T_{suffix}",
+                    "user_id": f"U_{suffix}",
+                    "user": f"bot-{suffix}",
+                    "team": f"Team {suffix}",
+                })
+                created_clients.append(self)
+
+        class FakeApp:
+            def __init__(self, token):
+                self.token = token
+                self.client = FakeWebClient(token)
+                self.registered_events = []
+                self.registered_commands = []
+                self.registered_actions = []
+                created_apps.append(self)
+
+            def event(self, event_type):
+                self.registered_events.append(event_type)
+
+                def decorator(fn):
+                    return fn
+
+                return decorator
+
+            def command(self, command_name):
+                self.registered_commands.append(command_name)
+
+                def decorator(fn):
+                    return fn
+
+                return decorator
+
+            def action(self, action_id):
+                self.registered_actions.append(action_id)
+
+                def decorator(fn):
+                    return fn
+
+                return decorator
+
+        class FakeSocketModeHandler:
+            def __init__(self, app, app_token, proxy=None):
+                self.app = app
+                self.app_token = app_token
+                self.proxy = proxy
+                self.client = MagicMock(proxy="constructor-default")
+
+            def start_async(self):
+                return None
+
+            async def close_async(self):
+                return None
+
+        config = PlatformConfig(enabled=True, token="xoxb-primary")
+        adapter = SlackAdapter(config)
+
+        with patch.object(_slack_mod, "AsyncApp", side_effect=FakeApp), \
+             patch.object(_slack_mod, "AsyncWebClient", side_effect=FakeWebClient), \
+             patch.object(_slack_mod, "AsyncSocketModeHandler", FakeSocketModeHandler), \
+             patch.object(_slack_mod, "_resolve_slack_proxy_url", return_value=None), \
+             patch.dict(os.environ, {"SLACK_APP_TOKEN": "xapp-fake"}, clear=False), \
+             patch("gateway.status.acquire_scoped_lock", return_value=(True, None)), \
+             patch("asyncio.create_task", return_value=MagicMock(name="socket-mode-task")):
+            result = await adapter.connect()
+
+        assert result is True
+        assert created_apps[0].client.proxy is None
+        assert all(client.proxy is None for client in created_clients)
+        assert adapter._handler is not None
+        assert adapter._handler.proxy is None
+        assert adapter._handler.client.proxy is None
+
+
 # ---------------------------------------------------------------------------
 # TestSendDocument
 # ---------------------------------------------------------------------------