diff --git a/gateway/platforms/telegram.py b/gateway/platforms/telegram.py
index d1935c8090..0b74c4e15f 100644
--- a/gateway/platforms/telegram.py
+++ b/gateway/platforms/telegram.py
@@ -1657,6 +1657,21 @@ class TelegramAdapter(BasePlatformAdapter):
         except Exception as exc:
             logger.error("Failed to write update response from callback: %s", exc)
 
+    def _missing_media_path_error(self, label: str, path: str) -> str:
+        """Build an actionable file-not-found error for gateway MEDIA delivery.
+
+        Paths like /workspace/... or /output/... often only exist inside the
+        Docker sandbox, while the gateway process runs on the host.
+        """
+        error = f"{label} file not found: {path}"
+        if path.startswith(("/workspace/", "/output/", "/outputs/")):
+            error += (
+                " (path may only exist inside the Docker sandbox. "
+                "Bind-mount a host directory and emit the host-visible "
+                "path in MEDIA: for gateway file delivery.)"
+            )
+        return error
+
     async def send_voice(
         self,
         chat_id: str,
@@ -1673,7 +1688,7 @@ class TelegramAdapter(BasePlatformAdapter):
         try:
             import os
             if not os.path.exists(audio_path):
-                return SendResult(success=False, error=f"Audio file not found: {audio_path}")
+                return SendResult(success=False, error=self._missing_media_path_error("Audio", audio_path))
             
             with open(audio_path, "rb") as audio_file:
                 # .ogg files -> send as voice (round playable bubble)
@@ -1722,7 +1737,7 @@ class TelegramAdapter(BasePlatformAdapter):
         try:
             import os
             if not os.path.exists(image_path):
-                return SendResult(success=False, error=f"Image file not found: {image_path}")
+                return SendResult(success=False, error=self._missing_media_path_error("Image", image_path))
 
             _thread = self._metadata_thread_id(metadata)
             with open(image_path, "rb") as image_file:
@@ -1759,14 +1774,7 @@ class TelegramAdapter(BasePlatformAdapter):
 
         try:
             if not os.path.exists(file_path):
-                error = f"File not found: {file_path}"
-                if file_path.startswith(("/workspace/", "/output/")):
-                    error += (
-                        " (path may only exist inside the Docker sandbox. "
-                        "Bind-mount a host directory and emit the host-visible "
-                        "path in MEDIA: for gateway file delivery.)"
-                    )
-                return SendResult(success=False, error=error)
+                return SendResult(success=False, error=self._missing_media_path_error("File", file_path))
 
             display_name = file_name or os.path.basename(file_path)
             _thread = self._metadata_thread_id(metadata)
@@ -1800,7 +1808,7 @@ class TelegramAdapter(BasePlatformAdapter):
 
         try:
             if not os.path.exists(video_path):
-                return SendResult(success=False, error=f"Video file not found: {video_path}")
+                return SendResult(success=False, error=self._missing_media_path_error("Video", video_path))
 
             _thread = self._metadata_thread_id(metadata)
             with open(video_path, "rb") as f:
diff --git a/gateway/run.py b/gateway/run.py
index d7dcaf1451..37b2723213 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -589,7 +589,7 @@ class GatewayRunner:
     def __init__(self, config: Optional[GatewayConfig] = None):
         self.config = config or load_gateway_config()
         self.adapters: Dict[Platform, BasePlatformAdapter] = {}
-        self._warn_if_docker_media_delivery_is_likely_misconfigured()
+        self._warn_if_docker_media_delivery_is_risky()
 
         # Load ephemeral config from config.yaml / env vars.
         # Both are injected at API-call time only and never persisted.
@@ -696,12 +696,14 @@ class GatewayRunner:
         self._background_tasks: set = set()
 
 
-    def _warn_if_docker_media_delivery_is_likely_misconfigured(self) -> None:
-        """Warn when Docker-backed gateway setups lack an obvious output bind mount.
+    def _warn_if_docker_media_delivery_is_risky(self) -> None:
+        """Warn when Docker-backed gateways lack an explicit export mount.
 
         MEDIA delivery happens in the gateway process, so paths emitted by the model
         must be readable from the host. A plain container-local path like
-        `/workspace/report.txt` often exists only inside Docker.
+        `/workspace/report.txt` or `/output/report.txt` often exists only inside
+        Docker, so users commonly need a dedicated export mount such as
+        `host-dir:/output`.
         """
         if os.getenv("TERMINAL_ENV", "").strip().lower() != "docker":
             return
@@ -737,8 +739,8 @@ class GatewayRunner:
         logger.warning(
             "Docker backend is enabled for the messaging gateway but no explicit host-visible "
             "output mount (for example '/home/user/.hermes/cache/documents:/output') is configured. "
-            "MEDIA file delivery can fail for files that only exist inside the container, such as "
-            "'/workspace/...'."
+            "This is fine if the model already emits host-visible paths, but MEDIA file delivery can fail "
+            "for container-local paths like '/workspace/...' or '/output/...'."
         )
 
 
diff --git a/tests/gateway/test_runner_startup_failures.py b/tests/gateway/test_runner_startup_failures.py
index ddcdd1aaa0..96d5d4627b 100644
--- a/tests/gateway/test_runner_startup_failures.py
+++ b/tests/gateway/test_runner_startup_failures.py
@@ -107,7 +107,6 @@ async def test_runner_allows_cron_only_mode_when_no_platforms_are_enabled(monkey
     assert state["gateway_state"] == "running"
 
 
-<<<<<<< HEAD
 @pytest.mark.asyncio
 async def test_runner_records_connected_platform_state_on_success(monkeypatch, tmp_path):
     monkeypatch.setenv("HERMES_HOME", str(tmp_path))
diff --git a/tests/gateway/test_telegram_documents.py b/tests/gateway/test_telegram_documents.py
index 2036f46a21..3a68139fa9 100644
--- a/tests/gateway/test_telegram_documents.py
+++ b/tests/gateway/test_telegram_documents.py
@@ -496,6 +496,19 @@ class TestSendDocument:
         assert "host-visible path" in result.error.lower()
         connected_adapter._bot.send_document.assert_not_called()
 
+    @pytest.mark.asyncio
+    async def test_send_document_outputs_path_has_docker_hint(self, connected_adapter):
+        """Legacy /outputs paths also get the Docker hint."""
+        result = await connected_adapter.send_document(
+            chat_id="12345",
+            file_path="/outputs/report.txt",
+        )
+
+        assert result.success is False
+        assert "docker sandbox" in result.error.lower()
+        assert "host-visible path" in result.error.lower()
+        connected_adapter._bot.send_document.assert_not_called()
+
     @pytest.mark.asyncio
     async def test_send_document_not_connected(self, adapter):
         """If bot is None, returns not connected error."""
@@ -678,6 +691,17 @@ class TestSendVideo:
         assert result.success is False
         assert "not found" in result.error.lower()
 
+    @pytest.mark.asyncio
+    async def test_send_video_workspace_path_has_docker_hint(self, connected_adapter):
+        result = await connected_adapter.send_video(
+            chat_id="12345",
+            video_path="/workspace/video.mp4",
+        )
+
+        assert result.success is False
+        assert "docker sandbox" in result.error.lower()
+        assert "host-visible path" in result.error.lower()
+
     @pytest.mark.asyncio
     async def test_send_video_not_connected(self, adapter):
         result = await adapter.send_video(