diff --git a/nanobot/cli/commands.py b/nanobot/cli/commands.py
index 3e71cb3ba..a248556b1 100644
--- a/nanobot/cli/commands.py
+++ b/nanobot/cli/commands.py
@@ -1189,6 +1189,17 @@ def _run_gateway(
         )
         return response
 
+    def _is_bound_cron_job(job: CronJob) -> bool:
+        payload = job.payload
+        if payload.kind != "agent_turn" or not payload.session_key:
+            return False
+        return not (
+            payload.deliver
+            or payload.channel
+            or payload.to
+            or payload.channel_meta
+        )
+
     async def _deliver_to_channel(
         msg: OutboundMessage, *, record: bool = False, session_key: str | None = None,
     ) -> None:
@@ -1349,7 +1360,7 @@ def _run_gateway(
                 logger.info("Heartbeat: silenced by post-run evaluation")
             return response
 
-        if job.payload.kind == "agent_turn" and job.payload.session_key:
+        if _is_bound_cron_job(job):
             return await _run_bound_cron_job(job)
 
         reminder_note = (
diff --git a/tests/cli/test_commands.py b/tests/cli/test_commands.py
index 01be99252..86901dab3 100644
--- a/tests/cli/test_commands.py
+++ b/tests/cli/test_commands.py
@@ -1373,6 +1373,151 @@ def test_gateway_cron_evaluator_receives_scheduled_reminder_context(
     }
 
 
+def test_gateway_legacy_cron_payloads_with_session_key_stay_legacy(
+    monkeypatch, tmp_path: Path
+) -> None:
+    config_file = _write_instance_config(tmp_path)
+    config = Config()
+    config.agents.defaults.workspace = str(tmp_path / "config-workspace")
+    bus = MagicMock()
+    bus.publish_outbound = AsyncMock()
+    seen: dict[str, object] = {"process_calls": [], "evaluations": [], "saved_keys": []}
+
+    class _FakeSession:
+        def __init__(self) -> None:
+            self.messages = []
+
+        def add_message(self, role: str, content: str, **kwargs) -> None:
+            self.messages.append({"role": role, "content": content, **kwargs})
+
+    class _FakeSessionManager:
+        def __init__(self, _workspace: Path) -> None:
+            self.session = _FakeSession()
+            seen["session_manager"] = self
+
+        def read_session_file(self, _key: str) -> dict[str, object]:
+            return {"metadata": {}}
+
+        def get_or_create(self, key: str) -> _FakeSession:
+            seen["saved_keys"].append(key)
+            return self.session
+
+        def save(self, session: _FakeSession) -> None:
+            seen["saved_session"] = session
+
+    class _FakeCron:
+        def __init__(self, _store_path: Path) -> None:
+            self.on_job = None
+            seen["cron"] = self
+
+    class _FakeAgentLoop:
+        @classmethod
+        def from_config(cls, config, bus=None, **extra):
+            return cls(**extra)
+
+        def __init__(self, *args, **kwargs) -> None:
+            self.model = "test-model"
+            self.provider = kwargs.get("provider", object())
+            self.tools = {}
+
+        async def process_direct(self, prompt: str, **kwargs):
+            seen["process_calls"].append((prompt, kwargs))
+            return OutboundMessage(
+                channel=kwargs["channel"],
+                chat_id=kwargs["chat_id"],
+                content="Legacy response.",
+            )
+
+        async def submit_automation_turn(self, _msg: InboundMessage):
+            raise AssertionError("legacy cron payload must not run as bound automation")
+
+        async def close_mcp(self) -> None:
+            return None
+
+        async def run(self) -> None:
+            return None
+
+        def stop(self) -> None:
+            return None
+
+    class _StopAfterCronSetup:
+        def __init__(self, *_args, **_kwargs) -> None:
+            raise _StopGatewayError("stop")
+
+    async def _capture_evaluate_response(*args, **_kwargs) -> bool:
+        seen["evaluations"].append(args)
+        return True
+
+    _patch_cli_command_runtime(
+        monkeypatch,
+        config,
+        message_bus=lambda: bus,
+        session_manager=_FakeSessionManager,
+        cron_service=_FakeCron,
+    )
+    monkeypatch.setattr("nanobot.cli.commands.AgentLoop", _FakeAgentLoop)
+    monkeypatch.setattr("nanobot.channels.manager.ChannelManager", _StopAfterCronSetup)
+    monkeypatch.setattr(
+        "nanobot.cli.commands.evaluate_response",
+        _capture_evaluate_response,
+    )
+
+    result = runner.invoke(app, ["gateway", "--config", str(config_file)])
+    assert isinstance(result.exception, _StopGatewayError)
+    cron = seen["cron"]
+
+    silent_job = CronJob(
+        id="silent-legacy",
+        name="Silent legacy",
+        payload=CronPayload(
+            message="Run silently.",
+            deliver=False,
+            channel="telegram",
+            to="user-1",
+            session_key="telegram:user-1",
+        ),
+    )
+
+    response = asyncio.run(cron.on_job(silent_job))
+
+    assert response == "Legacy response."
+    prompt, kwargs = seen["process_calls"][-1]
+    assert "Reminder: Run silently." in prompt
+    assert kwargs["session_key"] == "cron:silent-legacy"
+    assert kwargs["channel"] == "telegram"
+    assert kwargs["chat_id"] == "user-1"
+    assert seen["evaluations"] == []
+    bus.publish_outbound.assert_not_awaited()
+
+    topic_job = CronJob(
+        id="topic-legacy",
+        name="Topic legacy",
+        payload=CronPayload(
+            message="Ping the topic.",
+            deliver=True,
+            channel="telegram",
+            to="-100123",
+            channel_meta={"message_thread_id": 42},
+            session_key="telegram:-100123:topic:42",
+        ),
+    )
+
+    response = asyncio.run(cron.on_job(topic_job))
+
+    assert response == "Legacy response."
+    _prompt, kwargs = seen["process_calls"][-1]
+    assert kwargs["session_key"] == "cron:topic-legacy"
+    assert kwargs["channel"] == "telegram"
+    assert kwargs["chat_id"] == "-100123"
+    assert len(seen["evaluations"]) == 1
+    bus.publish_outbound.assert_awaited_once()
+    delivered = bus.publish_outbound.await_args.args[0]
+    assert delivered.channel == "telegram"
+    assert delivered.chat_id == "-100123"
+    assert delivered.metadata["message_thread_id"] == 42
+    assert seen["saved_keys"] == ["telegram:-100123:topic:42"]
+
+
 def test_gateway_bound_cron_runs_as_session_turn(
     monkeypatch, tmp_path: Path
 ) -> None: