diff --git a/services/cloud-agent-next/src/persistence/CloudAgentSession.ts b/services/cloud-agent-next/src/persistence/CloudAgentSession.ts
index ed5f60e16b..e3fe98910d 100644
--- a/services/cloud-agent-next/src/persistence/CloudAgentSession.ts
+++ b/services/cloud-agent-next/src/persistence/CloudAgentSession.ts
@@ -1702,14 +1702,22 @@ export class CloudAgentSession extends DurableObject<WorkerEnv> {
       return;
     }
 
+    const metadata = await this.getMetadata();
+    if (!metadata) {
+      return;
+    }
+
     const executions = await this.executionQueries.getAll();
     const latestExecution = executions[executions.length - 1];
-    if (!latestExecution) {
+
+    const lastActivity = latestExecution
+      ? (latestExecution.lastHeartbeat ?? latestExecution.completedAt ?? latestExecution.startedAt)
+      : (metadata.preparedAt ?? metadata.timestamp);
+
+    if (!lastActivity) {
       return;
     }
 
-    const lastActivity =
-      latestExecution.lastHeartbeat ?? latestExecution.completedAt ?? latestExecution.startedAt;
     const idleMs = now - lastActivity;
     const idleTimeoutMs = this.getKiloServerIdleTimeoutMs();
 
@@ -1717,11 +1725,6 @@ export class CloudAgentSession extends DurableObject<WorkerEnv> {
       return;
     }
 
-    const metadata = await this.getMetadata();
-    if (!metadata) {
-      return;
-    }
-
     logger
       .withFields({
         sessionId: this.sessionId,