diff --git a/gateway/run.py b/gateway/run.py
index 17ccd4c1c..07a1c93d7 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -19063,6 +19063,7 @@ class GatewayRunner(GatewayAuthorizationMixin, GatewayKanbanWatchersMixin, Gatew
                 next_message = pending
                 next_message_id = None
                 next_channel_prompt = None
+                next_session_key = session_key
                 if pending_event is not None:
                     next_source = getattr(pending_event, "source", None) or source
                     if self._is_goal_continuation_event(pending_event) and not self._goal_still_active_for_session(session_id):
@@ -19081,6 +19082,14 @@ class GatewayRunner(GatewayAuthorizationMixin, GatewayKanbanWatchersMixin, Gatew
                         return result
                     next_message_id = self._reply_anchor_for_event(pending_event)
                     next_channel_prompt = getattr(pending_event, "channel_prompt", None)
+                    try:
+                        next_session_key = self._session_key_for_source(next_source)
+                    except Exception:
+                        logger.debug(
+                            "Queued follow-up session-key resolution failed; reusing %s",
+                            session_key or "?",
+                            exc_info=True,
+                        )
 
                 # Restart typing indicator so the user sees activity while
                 # the follow-up turn runs.  The outer _process_message_background
@@ -19117,7 +19126,7 @@ class GatewayRunner(GatewayAuthorizationMixin, GatewayKanbanWatchersMixin, Gatew
                     history=updated_history,
                     source=next_source,
                     session_id=session_id,
-                    session_key=session_key,
+                    session_key=next_session_key,
                     run_generation=run_generation,
                     _interrupt_depth=_interrupt_depth + 1,
                     event_message_id=next_message_id,
diff --git a/tests/gateway/test_queued_native_image_session_key.py b/tests/gateway/test_queued_native_image_session_key.py
new file mode 100644
index 000000000..86ba1620a
--- /dev/null
+++ b/tests/gateway/test_queued_native_image_session_key.py
@@ -0,0 +1,151 @@
+import base64
+import importlib
+import sys
+import types
+from types import SimpleNamespace
+
+import pytest
+
+from gateway.config import Platform, PlatformConfig
+from gateway.platforms.base import BasePlatformAdapter, MessageEvent, MessageType, SendResult
+from gateway.session import SessionSource
+
+
+_ONE_BY_ONE_PNG = base64.b64decode(
+    "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mP8/x8AAwMCAO6L2ioAAAAASUVORK5CYII="
+)
+
+
+class CaptureAdapter(BasePlatformAdapter):
+    def __init__(self):
+        super().__init__(PlatformConfig(enabled=True, token="***"), Platform.TELEGRAM)
+        self.sent = []
+        self.typing = []
+
+    async def connect(self) -> bool:
+        return True
+
+    async def disconnect(self) -> None:
+        return None
+
+    async def send(self, chat_id, content, reply_to=None, metadata=None) -> SendResult:
+        self.sent.append(
+            {
+                "chat_id": chat_id,
+                "content": content,
+                "reply_to": reply_to,
+                "metadata": metadata,
+            }
+        )
+        return SendResult(success=True, message_id="sent-1")
+
+    async def send_typing(self, chat_id, metadata=None) -> None:
+        self.typing.append({"chat_id": chat_id, "metadata": metadata})
+
+    async def stop_typing(self, chat_id) -> None:
+        return None
+
+    async def get_chat_info(self, chat_id: str):
+        return {"id": chat_id}
+
+
+class CaptureQueuedNativeImageAgent:
+    calls = []
+
+    def __init__(self, **kwargs):
+        self.tools = []
+        self.tool_progress_callback = kwargs.get("tool_progress_callback")
+
+    def run_conversation(self, message, conversation_history=None, task_id=None):
+        type(self).calls.append(message)
+        return {
+            "final_response": f"done-{len(type(self).calls)}",
+            "messages": [],
+            "api_calls": 1,
+        }
+
+
+def _make_runner(adapter):
+    gateway_run = importlib.import_module("gateway.run")
+    runner = object.__new__(gateway_run.GatewayRunner)
+    runner.adapters = {adapter.platform: adapter}
+    runner._voice_mode = {}
+    runner._prefill_messages = []
+    runner._ephemeral_system_prompt = ""
+    runner._reasoning_config = None
+    runner._provider_routing = {}
+    runner._fallback_model = None
+    runner._session_db = None
+    runner._running_agents = {}
+    runner._session_run_generation = {}
+    runner.hooks = SimpleNamespace(loaded_hooks=False)
+    runner.config = SimpleNamespace(
+        thread_sessions_per_user=False,
+        group_sessions_per_user=False,
+        stt_enabled=False,
+    )
+    runner._model = "openai/gpt-4.1-mini"
+    runner._base_url = None
+    runner._decide_image_input_mode = lambda: "native"
+    return runner
+
+
+@pytest.mark.asyncio
+async def test_queued_followup_uses_pending_event_session_key_for_native_images(monkeypatch, tmp_path):
+    CaptureQueuedNativeImageAgent.calls = []
+
+    fake_dotenv = types.ModuleType("dotenv")
+    fake_dotenv.load_dotenv = lambda *args, **kwargs: None
+    monkeypatch.setitem(sys.modules, "dotenv", fake_dotenv)
+
+    fake_run_agent = types.ModuleType("run_agent")
+    fake_run_agent.AIAgent = CaptureQueuedNativeImageAgent
+    monkeypatch.setitem(sys.modules, "run_agent", fake_run_agent)
+
+    gateway_run = importlib.import_module("gateway.run")
+    monkeypatch.setattr(gateway_run, "_hermes_home", tmp_path)
+    monkeypatch.setattr(gateway_run, "_resolve_runtime_agent_kwargs", lambda: {"api_key": "***"})
+
+    adapter = CaptureAdapter()
+    runner = _make_runner(adapter)
+
+    image_path = tmp_path / "queued-image.png"
+    image_path.write_bytes(_ONE_BY_ONE_PNG)
+
+    source = SessionSource(
+        platform=Platform.TELEGRAM,
+        chat_id="-1001",
+        chat_type="group",
+    )
+    pending_source = SessionSource(
+        platform=Platform.TELEGRAM,
+        chat_id="-1001",
+        chat_type="group",
+        thread_id="17585",
+    )
+
+    adapter._pending_messages["agent:main:telegram:group:-1001"] = MessageEvent(
+        text="describe this",
+        message_type=MessageType.PHOTO,
+        source=pending_source,
+        media_urls=[str(image_path)],
+        media_types=["image/png"],
+        message_id="queued-1",
+    )
+
+    result = await runner._run_agent(
+        message="hello",
+        context_prompt="",
+        history=[],
+        source=source,
+        session_id="sess-native-image-followup",
+        session_key="agent:main:telegram:group:-1001",
+    )
+
+    assert result["final_response"] == "done-2"
+    assert len(CaptureQueuedNativeImageAgent.calls) == 2
+    queued_message = CaptureQueuedNativeImageAgent.calls[1]
+    assert isinstance(queued_message, list)
+    assert queued_message[0]["type"] == "text"
+    assert queued_message[0]["text"].startswith("describe this")
+    assert any(part.get("type") == "image_url" for part in queued_message)