diff --git a/nanobot/cli/gateway_runtime.py b/nanobot/cli/gateway_runtime.py
index c5feee52e..b65fbdbb6 100644
--- a/nanobot/cli/gateway_runtime.py
+++ b/nanobot/cli/gateway_runtime.py
@@ -785,8 +785,10 @@ def _run_gateway(
         console.print(f"[green]✓[/green] Dream: {dream_cfg.describe_schedule()}")
     else:
         console.print("[yellow]○[/yellow] Dream: disabled")
-        cron.remove_system_job("dream")
+        # Advance the cursor first: it must happen unconditionally (issue
+        # #4242), even if the cron store turns out to be corrupt below.
         _advance_dream_cursor_if_behind(agent.context.memory)
+        cron.remove_system_job("dream")
 
     # Register Heartbeat system job (idempotent on restart)
     if hb_cfg.enabled:
diff --git a/tests/cli/test_commands.py b/tests/cli/test_commands.py
index 228b4c4f4..7ae494d7e 100644
--- a/tests/cli/test_commands.py
+++ b/tests/cli/test_commands.py
@@ -3221,7 +3221,8 @@ def test_gateway_local_trigger_queue_submits_agent_turns(
         def register_system_job(self, _job) -> None:
             return None
 
-        def remove_system_job(self, _job_id: str) -> bool:
+        def remove_system_job(self, job_id: str) -> bool:
+            seen.setdefault("removed_system_jobs", []).append(job_id)
             return False
 
     class _FakeAgentLoop(_GatewayAgentContractStub):
@@ -3300,6 +3301,8 @@ def test_gateway_local_trigger_queue_submits_agent_turns(
     turn_delivery_factory = agent_kwargs["turn_delivery_factory"]
     assert isinstance(turn_delivery_factory, TurnDeliveryFactory)
     assert turn_delivery_factory.bus is bus
+    # Disabled system jobs must be retired on startup, not just unregistered.
+    assert seen["removed_system_jobs"] == ["dream", "heartbeat"]
     assert isinstance(turn_delivery_factory.route_policy, WebuiTurnRoutePolicy)
     assert turn_delivery_factory.route_policy.sessions is agent.sessions
 
diff --git a/tests/cron/test_cron_service.py b/tests/cron/test_cron_service.py
index 3653ae6da..fa1c3fb32 100644
--- a/tests/cron/test_cron_service.py
+++ b/tests/cron/test_cron_service.py
@@ -818,6 +818,15 @@ def test_remove_system_job_retires_persisted_system_job(tmp_path) -> None:
     assert other.remove_job("dream") == "protected"
 
 
+def test_remove_system_job_without_store_file(tmp_path) -> None:
+    """Fresh install with the system job disabled: no jobs.json exists yet."""
+    store_path = tmp_path / "cron" / "jobs.json"
+    service = CronService(store_path)
+
+    assert service.remove_system_job("heartbeat") is False
+    assert not store_path.exists()
+
+
 @pytest.mark.asyncio
 async def test_start_server_not_jobs(tmp_path):
     store_path = tmp_path / "cron" / "jobs.json"