diff --git a/src/cron/isolated-agent/run-executor.ts b/src/cron/isolated-agent/run-executor.ts
index 70e80009b02e..e12ca8baeca2 100644
--- a/src/cron/isolated-agent/run-executor.ts
+++ b/src/cron/isolated-agent/run-executor.ts
@@ -322,6 +322,7 @@ export function createCronPromptExecutor(params: {
             agentId: params.agentId,
             trigger: "cron",
             jobId: params.job.id,
+            cleanupCliLiveSessionOnRunEnd: params.job.sessionTarget === "isolated",
             sessionFile,
             workspaceDir: params.workspaceDir,
             config: params.cfgWithAgentDefaults,
diff --git a/src/cron/isolated-agent/run.session-key-isolation.test.ts b/src/cron/isolated-agent/run.session-key-isolation.test.ts
index 0a7d2bc63197..76cbc19f1b65 100644
--- a/src/cron/isolated-agent/run.session-key-isolation.test.ts
+++ b/src/cron/isolated-agent/run.session-key-isolation.test.ts
@@ -198,6 +198,7 @@ describe("runCronIsolatedAgentTurn isolated session identity", () => {
       promptCacheKey?: string;
       bootstrapContextMode?: string;
       bootstrapContextRunKind?: string;
+      cleanupCliLiveSessionOnRunEnd?: boolean;
     };
     expect(runRequest.sessionId).toBe("isolated-cli-run-1");
     expect(runRequest.sessionKey).toBe("agent:default:cron:cli-monitor:run:isolated-cli-run-1");
@@ -205,6 +206,7 @@ describe("runCronIsolatedAgentTurn isolated session identity", () => {
     expect(runRequest.promptCacheKey).toBeUndefined();
     expect(runRequest.bootstrapContextMode).toBe("lightweight");
     expect(runRequest.bootstrapContextRunKind).toBe("cron");
+    expect(runRequest.cleanupCliLiveSessionOnRunEnd).toBe(true);
   });
 
   it("runs externally sourced CLI hook turns", async () => {