diff --git a/gateway/run.py b/gateway/run.py
index 5ef376a9b..293daa959 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -4822,7 +4822,7 @@ class GatewayRunner:
                                         try:
                                             _adapter = self.adapters.get(source.platform)
                                             if _adapter and source.chat_id:
-                                                await _adapter.send(source.chat_id, _warn_msg)
+                                                await _adapter.send(source.chat_id, _warn_msg, metadata=_hyg_meta)
                                         except Exception as _werr:
                                             logger.warning(
                                                 "Failed to deliver compression-failure warning to user: %s",
diff --git a/tests/gateway/test_session_hygiene.py b/tests/gateway/test_session_hygiene.py
index f2e343441..555a8d7d4 100644
--- a/tests/gateway/test_session_hygiene.py
+++ b/tests/gateway/test_session_hygiene.py
@@ -393,3 +393,119 @@ async def test_session_hygiene_messages_stay_in_originating_topic(monkeypatch, t
     assert FakeCompressAgent.last_instance is not None
     FakeCompressAgent.last_instance.shutdown_memory_provider.assert_called_once()
     FakeCompressAgent.last_instance.close.assert_called_once()
+
+
+@pytest.mark.asyncio
+async def test_session_hygiene_warns_user_when_summary_generation_fails(monkeypatch, tmp_path):
+    """When auxiliary compression's summary LLM call fails, the compressor
+    inserts a static fallback and the dropped turns are unrecoverable.
+    Gateway must surface a visible ⚠️ warning to the user, including
+    thread_id metadata so it lands in the originating topic/thread."""
+    fake_dotenv = types.ModuleType("dotenv")
+    fake_dotenv.load_dotenv = lambda *args, **kwargs: None
+    monkeypatch.setitem(sys.modules, "dotenv", fake_dotenv)
+
+    class FakeCompressAgentWithSummaryFailure:
+        last_instance = None
+
+        def __init__(self, **kwargs):
+            self.model = kwargs.get("model")
+            self.session_id = kwargs.get("session_id", "fake-session")
+            self._print_fn = None
+            self.shutdown_memory_provider = MagicMock()
+            self.close = MagicMock()
+            # Simulate a compressor that hit summary-generation failure
+            # and inserted the static fallback placeholder.
+            self.context_compressor = SimpleNamespace(
+                _last_summary_fallback_used=True,
+                _last_summary_dropped_count=42,
+                _last_summary_error="404 model not found: gemini-3-flash-preview",
+            )
+            type(self).last_instance = self
+
+        def _compress_context(self, messages, *_args, **_kwargs):
+            self.session_id = f"{self.session_id}_compressed"
+            return ([{"role": "assistant", "content": "compressed"}], None)
+
+    fake_run_agent = types.ModuleType("run_agent")
+    fake_run_agent.AIAgent = FakeCompressAgentWithSummaryFailure
+    monkeypatch.setitem(sys.modules, "run_agent", fake_run_agent)
+
+    gateway_run = importlib.import_module("gateway.run")
+    GatewayRunner = gateway_run.GatewayRunner
+
+    adapter = HygieneCaptureAdapter()
+    runner = object.__new__(GatewayRunner)
+    runner.config = GatewayConfig(
+        platforms={Platform.TELEGRAM: PlatformConfig(enabled=True, token="fake-token")}
+    )
+    runner.adapters = {Platform.TELEGRAM: adapter}
+    runner._voice_mode = {}
+    runner.hooks = SimpleNamespace(emit=AsyncMock(), loaded_hooks=False)
+    runner.session_store = MagicMock()
+    runner.session_store.get_or_create_session.return_value = SessionEntry(
+        session_key="agent:main:telegram:group:-1001:17585",
+        session_id="sess-1",
+        created_at=datetime.now(),
+        updated_at=datetime.now(),
+        platform=Platform.TELEGRAM,
+        chat_type="group",
+    )
+    runner.session_store.load_transcript.return_value = _make_history(6, content_size=400)
+    runner.session_store.has_any_sessions.return_value = True
+    runner.session_store.rewrite_transcript = MagicMock()
+    runner.session_store.append_to_transcript = MagicMock()
+    runner._running_agents = {}
+    runner._pending_messages = {}
+    runner._pending_approvals = {}
+    runner._session_db = None
+    runner._is_user_authorized = lambda _source: True
+    runner._set_session_env = lambda _context: None
+    runner._run_agent = AsyncMock(
+        return_value={
+            "final_response": "ok",
+            "messages": [],
+            "tools": [],
+            "history_offset": 0,
+            "last_prompt_tokens": 0,
+        }
+    )
+
+    monkeypatch.setattr(gateway_run, "_hermes_home", tmp_path)
+    monkeypatch.setattr(gateway_run, "_resolve_runtime_agent_kwargs", lambda: {"api_key": "***"})
+    monkeypatch.setattr(
+        "agent.model_metadata.get_model_context_length",
+        lambda *_args, **_kwargs: 100,
+    )
+    monkeypatch.setenv("TELEGRAM_HOME_CHANNEL", "795544298")
+
+    event = MessageEvent(
+        text="hello",
+        source=SessionSource(
+            platform=Platform.TELEGRAM,
+            chat_id="-1001",
+            chat_type="group",
+            thread_id="17585",
+            user_id="12345",
+        ),
+        message_id="1",
+    )
+
+    result = await runner._handle_message(event)
+
+    assert result == "ok"
+    # The compressor reported summary-failure → exactly one warning
+    # message must have been delivered to the user.
+    warning_messages = [s for s in adapter.sent if "Context compression summary failed" in s["content"]]
+    assert len(warning_messages) == 1, (
+        f"Expected 1 compression-failure warning, got {len(warning_messages)}: {adapter.sent}"
+    )
+    warn = warning_messages[0]
+    # Warning must include the dropped count and the underlying error.
+    assert "42" in warn["content"]
+    assert "404" in warn["content"]
+    # Warning must land in the originating topic/thread, not the main channel.
+    assert warn["chat_id"] == "-1001"
+    assert warn["metadata"] == {"thread_id": "17585"}
+
+    FakeCompressAgentWithSummaryFailure.last_instance.close.assert_called_once()
\ No newline at end of file