diff --git a/src/agents/pi-embedded-runner/context-engine-maintenance.test.ts b/src/agents/pi-embedded-runner/context-engine-maintenance.test.ts
index cd8535529a8..6b91419dc28 100644
--- a/src/agents/pi-embedded-runner/context-engine-maintenance.test.ts
+++ b/src/agents/pi-embedded-runner/context-engine-maintenance.test.ts
@@ -394,7 +394,7 @@ describe("runContextEngineMaintenance", () => {
     });
   });
 
-  it("coalesces repeated turn maintenance requests for the same session", async () => {
+  it("coalesces repeated requests into one active run plus one follow-up run for the same session", async () => {
     await withStateDirEnv("openclaw-turn-maintenance-", async () => {
       vi.useFakeTimers();
       try {
@@ -456,10 +456,12 @@ describe("runContextEngineMaintenance", () => {
         expect(queuedTasks).toHaveLength(1);
 
         releaseForeground();
-        await waitForAssertion(() => expect(maintain).toHaveBeenCalledTimes(1));
-        expect(getTaskById(queuedTasks[0].taskId)).toMatchObject({
-          status: "succeeded",
-        });
+        await waitForAssertion(() => expect(maintain).toHaveBeenCalledTimes(2));
+        const completedTasks = listTasksForOwnerKey(sessionKey).filter(
+          (task) => task.taskKind === TURN_MAINTENANCE_TASK_KIND,
+        );
+        expect(completedTasks).toHaveLength(2);
+        expect(completedTasks.every((task) => task.status === "succeeded")).toBe(true);
 
         await foregroundTurn;
       } finally {
@@ -468,6 +470,78 @@ describe("runContextEngineMaintenance", () => {
     });
   });
 
+  it("queues a follow-up maintenance run when a new turn finishes during an active deferred run", async () => {
+    await withStateDirEnv("openclaw-turn-maintenance-rerun-", async () => {
+      vi.useFakeTimers();
+      try {
+        resetCommandQueueStateForTest();
+        resetTaskRegistryForTests({ persist: false });
+        resetTaskFlowRegistryForTests({ persist: false });
+
+        const sessionKey = "agent:main:session-rerun";
+        let releaseFirstMaintenance!: () => void;
+        let maintenanceCalls = 0;
+        const maintain = vi.fn(async () => {
+          maintenanceCalls += 1;
+          if (maintenanceCalls === 1) {
+            await new Promise<void>((resolve) => {
+              releaseFirstMaintenance = resolve;
+            });
+          }
+          return {
+            changed: false,
+            bytesFreed: 0,
+            rewrittenEntries: 0,
+          };
+        });
+
+        const backgroundEngine = {
+          info: {
+            id: "test",
+            name: "Test Engine",
+            turnMaintenanceMode: "background" as const,
+          },
+          ingest: async () => ({ ingested: true }),
+          assemble: async ({ messages }: { messages: unknown[] }) => ({
+            messages,
+            estimatedTokens: 0,
+          }),
+          compact: async () => ({ ok: true, compacted: false }),
+          maintain,
+        } as NonNullable<Parameters<typeof runContextEngineMaintenance>[0]["contextEngine"]>;
+
+        await runContextEngineMaintenance({
+          contextEngine: backgroundEngine,
+          sessionId: "session-rerun",
+          sessionKey,
+          sessionFile: "/tmp/session-rerun.jsonl",
+          reason: "turn",
+        });
+
+        await waitForAssertion(() => expect(maintain).toHaveBeenCalledTimes(1));
+
+        await runContextEngineMaintenance({
+          contextEngine: backgroundEngine,
+          sessionId: "session-rerun",
+          sessionKey,
+          sessionFile: "/tmp/session-rerun.jsonl",
+          reason: "turn",
+        });
+
+        releaseFirstMaintenance();
+        await waitForAssertion(() => expect(maintain).toHaveBeenCalledTimes(2));
+
+        const tasks = listTasksForOwnerKey(sessionKey).filter(
+          (task) => task.taskKind === TURN_MAINTENANCE_TASK_KIND,
+        );
+        expect(tasks).toHaveLength(2);
+        expect(tasks.every((task) => task.status === "succeeded")).toBe(true);
+      } finally {
+        vi.useRealTimers();
+      }
+    });
+  });
+
   it("replaces legacy active maintenance tasks that are missing a runId", async () => {
     await withStateDirEnv("openclaw-turn-maintenance-", async () => {
       vi.useFakeTimers();
diff --git a/src/agents/pi-embedded-runner/context-engine-maintenance.ts b/src/agents/pi-embedded-runner/context-engine-maintenance.ts
index b1230ae3c76..2709bc64117 100644
--- a/src/agents/pi-embedded-runner/context-engine-maintenance.ts
+++ b/src/agents/pi-embedded-runner/context-engine-maintenance.ts
@@ -35,7 +35,22 @@ const TURN_MAINTENANCE_TASK_TASK = "Deferred context-engine maintenance after tu
 const TURN_MAINTENANCE_LANE_PREFIX = "context-engine-turn-maintenance:";
 const TURN_MAINTENANCE_WAIT_POLL_MS = 100;
 const TURN_MAINTENANCE_LONG_WAIT_MS = 10_000;
-const activeDeferredTurnMaintenanceRuns = new Map<string, Promise<void>>();
+type DeferredTurnMaintenanceScheduleParams = {
+  contextEngine: ContextEngine;
+  sessionId: string;
+  sessionKey: string;
+  sessionFile: string;
+  sessionManager?: Parameters<typeof rewriteTranscriptEntriesInSessionManager>[0]["sessionManager"];
+  runtimeContext?: ContextEngineRuntimeContext;
+};
+
+type DeferredTurnMaintenanceRunState = {
+  promise: Promise<void>;
+  rerunRequested: boolean;
+  latestParams: DeferredTurnMaintenanceScheduleParams;
+};
+
+const activeDeferredTurnMaintenanceRuns = new Map<string, DeferredTurnMaintenanceRunState>();
 
 function normalizeSessionKey(sessionKey?: string): string | undefined {
   return normalizeOptionalString(sessionKey) || undefined;
@@ -357,19 +372,15 @@ async function runDeferredTurnMaintenanceWorker(params: {
   }
 }
 
-function scheduleDeferredTurnMaintenance(params: {
-  contextEngine: ContextEngine;
-  sessionId: string;
-  sessionKey: string;
-  sessionFile: string;
-  sessionManager?: Parameters<typeof rewriteTranscriptEntriesInSessionManager>[0]["sessionManager"];
-  runtimeContext?: ContextEngineRuntimeContext;
-}): void {
+function scheduleDeferredTurnMaintenance(params: DeferredTurnMaintenanceScheduleParams): void {
   const sessionKey = normalizeSessionKey(params.sessionKey);
   if (!sessionKey) {
     return;
   }
-  if (activeDeferredTurnMaintenanceRuns.has(sessionKey)) {
+  const activeRun = activeDeferredTurnMaintenanceRuns.get(sessionKey);
+  if (activeRun) {
+    activeRun.rerunRequested = true;
+    activeRun.latestParams = { ...params, sessionKey };
     return;
   }
 
@@ -414,14 +425,28 @@ function scheduleDeferredTurnMaintenance(params: {
         runId: task.runId!,
       }),
   );
+  let state!: DeferredTurnMaintenanceRunState;
   const trackedPromise = runPromise
     .catch((err) => {
       log.warn(`failed to schedule deferred context engine maintenance: ${String(err)}`);
     })
     .finally(() => {
+      const current = activeDeferredTurnMaintenanceRuns.get(sessionKey);
+      if (current !== state) {
+        return;
+      }
+      const rerunParams = current.rerunRequested ? current.latestParams : undefined;
       activeDeferredTurnMaintenanceRuns.delete(sessionKey);
+      if (rerunParams) {
+        scheduleDeferredTurnMaintenance(rerunParams);
+      }
     });
-  activeDeferredTurnMaintenanceRuns.set(sessionKey, trackedPromise);
+  state = {
+    promise: trackedPromise,
+    rerunRequested: false,
+    latestParams: { ...params, sessionKey },
+  };
+  activeDeferredTurnMaintenanceRuns.set(sessionKey, state);
   void trackedPromise;
 }