diff --git a/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test-support.ts b/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test-support.ts
index e394a0040..bb04412bd 100644
--- a/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test-support.ts
+++ b/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test-support.ts
@@ -75,6 +75,7 @@ export function createMockContext(): PluginInput {
 
 export function setupDelayedTimeoutMocks(): {
   createUntrackedTimeout: () => ReturnType<typeof setTimeout>
+  runScheduledTimeout: (index: number) => void
   restore: () => void
   getClearTimeoutCalls: () => Array<ReturnType<typeof setTimeout>>
   getScheduledTimeouts: () => Array<ReturnType<typeof setTimeout>>
@@ -83,6 +84,7 @@ export function setupDelayedTimeoutMocks(): {
   const originalClearTimeout = globalThis.clearTimeout
   const clearTimeoutCalls: Array<ReturnType<typeof setTimeout>> = []
   const scheduledTimeouts: Array<ReturnType<typeof setTimeout>> = []
+  const scheduledCallbacks: Array<() => void> = []
 
   function createTimeoutHandle(): ReturnType<typeof setTimeout> {
     const timeoutID = originalSetTimeout(() => {}, 60_000)
@@ -90,9 +92,10 @@ export function setupDelayedTimeoutMocks(): {
     return timeoutID
   }
 
-  globalThis.setTimeout = ((_: () => void, _delay?: number) => {
+  globalThis.setTimeout = ((callback: () => void, _delay?: number) => {
     const timeoutID = createTimeoutHandle()
     scheduledTimeouts.push(timeoutID)
+    scheduledCallbacks.push(callback)
     return timeoutID
   }) as typeof setTimeout
 
@@ -103,6 +106,9 @@ export function setupDelayedTimeoutMocks(): {
 
   return {
     createUntrackedTimeout: createTimeoutHandle,
+    runScheduledTimeout: (index: number) => {
+      scheduledCallbacks[index]?.()
+    },
     restore: () => {
       globalThis.setTimeout = originalSetTimeout
       globalThis.clearTimeout = originalClearTimeout
diff --git a/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test.ts b/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test.ts
index 4291bb754..6300ab55e 100644
--- a/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test.ts
+++ b/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test.ts
@@ -94,4 +94,45 @@ describe("createAnthropicContextWindowLimitRecoveryHook", () => {
     }
   })
 
+  test("#given active pending and retry timers #when dispose is called #then it clears both timer maps", async () => {
+    //#given
+    const { createUntrackedTimeout, getClearTimeoutCalls, getScheduledTimeouts, restore, runScheduledTimeout } =
+      setupDelayedTimeoutMocks()
+    executeCompactMock.mockImplementationOnce(async (...args: Parameters<typeof executeCompactMock>) => {
+      const sessionID = args[0]
+      const autoCompactState = args[2]
+
+      autoCompactState.retryTimerBySession.set(sessionID, createUntrackedTimeout())
+    })
+    const hook = createRecoveryHook()
+
+    try {
+      await hook.event({
+        event: {
+          type: "session.error",
+          properties: { sessionID: "session-retry", error: "prompt is too long" },
+        },
+      })
+
+      await hook.event({
+        event: {
+          type: "session.error",
+          properties: { sessionID: "session-pending", error: "prompt is too long" },
+        },
+      })
+
+      runScheduledTimeout(0)
+
+      const [retryTimer, pendingTimer] = getScheduledTimeouts()
+
+      //#when
+      hook.dispose()
+
+      //#then
+      expect(getClearTimeoutCalls()).toEqual(expect.arrayContaining([retryTimer, pendingTimer]))
+    } finally {
+      restore()
+    }
+  })
+
 })