diff --git a/src/hooks/todo-continuation-enforcer/non-idle-events.test.ts b/src/hooks/todo-continuation-enforcer/non-idle-events.test.ts
index b0030118d..ef23a761b 100644
--- a/src/hooks/todo-continuation-enforcer/non-idle-events.test.ts
+++ b/src/hooks/todo-continuation-enforcer/non-idle-events.test.ts
@@ -67,4 +67,35 @@ describe("handleNonIdleEvent", () => {
     expect(state.wasCancelled).toBe(true)
     expect(state.tokenLimitDetected).toBe(true)
   })
+
+  test("given ultrawork loop continuation user message update, cancels stale todo continuation countdown", () => {
+    // given
+    const sessionID = "ses_ulw_todo_overlap"
+    const state = sessionStateStore.getState(sessionID)
+    state.countdownStartedAt = Date.now() - 10_000
+    state.wasCancelled = true
+    state.tokenLimitDetected = true
+
+    // when
+    handleNonIdleEvent({
+      eventType: "message.updated",
+      properties: {
+        sessionID,
+        info: { role: "user" },
+        parts: [
+          {
+            type: "text",
+            text: `ultrawork [SYSTEM DIRECTIVE: OH-MY-OPENCODE - RALPH LOOP 2/500]\ncontinue\n${OMO_INTERNAL_INITIATOR_MARKER}`,
+            synthetic: true,
+          },
+        ],
+      },
+      sessionStateStore,
+    })
+
+    // then
+    expect(state.countdownStartedAt).toBeUndefined()
+    expect(state.wasCancelled).toBe(true)
+    expect(state.tokenLimitDetected).toBe(true)
+  })
 })
diff --git a/src/hooks/todo-continuation-enforcer/non-idle-events.ts b/src/hooks/todo-continuation-enforcer/non-idle-events.ts
index d54ae6273..acf685592 100644
--- a/src/hooks/todo-continuation-enforcer/non-idle-events.ts
+++ b/src/hooks/todo-continuation-enforcer/non-idle-events.ts
@@ -2,6 +2,7 @@ import { resolveMessageEventSessionID, resolveSessionEventID } from "../../share
 import type { InternalInitiatorTextPartLike } from "../../shared/internal-initiator-marker"
 import { isSyntheticOrInternalOnlyTextParts } from "../../shared/internal-initiator-marker"
 import { log } from "../../shared/logger"
+import { isSystemDirective } from "../../shared/system-directive"
 
 import { COUNTDOWN_GRACE_PERIOD_MS, HOOK_NAME } from "./constants"
 import type { SessionStateStore } from "./session-state"
@@ -34,6 +35,14 @@ function resolveEventParts(
   return parts
 }
 
+function hasInternalSystemDirective(parts: InternalInitiatorTextPartLike[] | undefined): boolean {
+  return (parts ?? []).some(
+    (part) => part.type === "text"
+      && typeof part.text === "string"
+      && isSystemDirective(part.text),
+  )
+}
+
 export function handleNonIdleEvent(args: {
   eventType: string
   properties: Record<string, unknown> | undefined
@@ -50,6 +59,11 @@ export function handleNonIdleEvent(args: {
     if (role === "user") {
       const parts = resolveEventParts(properties)
       if (isSyntheticOrInternalOnlyTextParts(parts)) {
+        const state = sessionStateStore.getExistingState(sessionID)
+        if (state?.countdownStartedAt && hasInternalSystemDirective(parts)) {
+          sessionStateStore.cancelCountdown(sessionID)
+          log(`[${HOOK_NAME}] Cancelled countdown for internal continuation message`, { sessionID })
+        }
         log(`[${HOOK_NAME}] Ignoring synthetic/internal user message event`, { sessionID })
         return
       }