diff --git a/src/hooks/todo-continuation-enforcer/constants.ts b/src/hooks/todo-continuation-enforcer/constants.ts
index 03e7d01fd..f8b94fdef 100644
--- a/src/hooks/todo-continuation-enforcer/constants.ts
+++ b/src/hooks/todo-continuation-enforcer/constants.ts
@@ -17,3 +17,5 @@ export const TOAST_DURATION_MS = 900
 export const COUNTDOWN_GRACE_PERIOD_MS = 500
 
 export const ABORT_WINDOW_MS = 3000
+export const CONTINUATION_COOLDOWN_MS = 30_000
+export const MAX_UNCHANGED_CYCLES = 3
diff --git a/src/hooks/todo-continuation-enforcer/continuation-injection.ts b/src/hooks/todo-continuation-enforcer/continuation-injection.ts
index 2e8911323..2c67fa78a 100644
--- a/src/hooks/todo-continuation-enforcer/continuation-injection.ts
+++ b/src/hooks/todo-continuation-enforcer/continuation-injection.ts
@@ -114,6 +114,11 @@ export async function injectContinuation(args: {
 Remaining tasks:
 ${todoList}`
 
+  const injectionState = sessionStateStore.getExistingState(sessionID)
+  if (injectionState) {
+    injectionState.inFlight = true
+  }
+
   try {
     log(`[${HOOK_NAME}] Injecting continuation`, {
       sessionID,
@@ -133,7 +138,14 @@ ${todoList}`
     })
 
     log(`[${HOOK_NAME}] Injection successful`, { sessionID })
+    if (injectionState) {
+      injectionState.inFlight = false
+      injectionState.lastInjectedAt = Date.now()
+    }
   } catch (error) {
     log(`[${HOOK_NAME}] Injection failed`, { sessionID, error: String(error) })
+    if (injectionState) {
+      injectionState.inFlight = false
+    }
   }
 }
diff --git a/src/hooks/todo-continuation-enforcer/idle-event.ts b/src/hooks/todo-continuation-enforcer/idle-event.ts
index 86d3e504f..c5181d486 100644
--- a/src/hooks/todo-continuation-enforcer/idle-event.ts
+++ b/src/hooks/todo-continuation-enforcer/idle-event.ts
@@ -8,8 +8,10 @@ import { log } from "../../shared/logger"
 
 import {
   ABORT_WINDOW_MS,
+  CONTINUATION_COOLDOWN_MS,
   DEFAULT_SKIP_AGENTS,
   HOOK_NAME,
+  MAX_UNCHANGED_CYCLES,
 } from "./constants"
 import { isLastAssistantMessageAborted } from "./abort-detection"
 import { getIncompleteCount } from "./todo"
@@ -105,6 +107,29 @@ export async function handleSessionIdle(args: {
     return
   }
 
+  if (state.inFlight) {
+    log(`[${HOOK_NAME}] Skipped: injection in flight`, { sessionID })
+    return
+  }
+
+  if (state.lastInjectedAt && Date.now() - state.lastInjectedAt < CONTINUATION_COOLDOWN_MS) {
+    log(`[${HOOK_NAME}] Skipped: cooldown active`, { sessionID })
+    return
+  }
+
+  const incompleteTodos = todos.filter((todo) => todo.status !== "completed" && todo.status !== "cancelled")
+  const todoHash = incompleteTodos.map((todo) => `${todo.id}:${todo.status}`).join("|")
+  if (state.lastTodoHash === todoHash) {
+    state.unchangedCycles = (state.unchangedCycles ?? 0) + 1
+    if (state.unchangedCycles >= MAX_UNCHANGED_CYCLES) {
+      log(`[${HOOK_NAME}] Skipped: stagnation cap reached`, { sessionID, cycles: state.unchangedCycles })
+      return
+    }
+  } else {
+    state.unchangedCycles = 0
+  }
+  state.lastTodoHash = todoHash
+
   let resolvedInfo: ResolvedMessageInfo | undefined
   let hasCompactionMessage = false
   try {
diff --git a/src/hooks/todo-continuation-enforcer/session-state.ts b/src/hooks/todo-continuation-enforcer/session-state.ts
index fc96437ab..904e0a8fe 100644
--- a/src/hooks/todo-continuation-enforcer/session-state.ts
+++ b/src/hooks/todo-continuation-enforcer/session-state.ts
@@ -38,6 +38,7 @@ export function createSessionStateStore(): SessionStateStore {
       state.countdownInterval = undefined
     }
 
+    state.inFlight = false
     state.countdownStartedAt = undefined
   }
 
diff --git a/src/hooks/todo-continuation-enforcer/todo-continuation-enforcer.test.ts b/src/hooks/todo-continuation-enforcer/todo-continuation-enforcer.test.ts
index 760165dd7..43c681baf 100644
--- a/src/hooks/todo-continuation-enforcer/todo-continuation-enforcer.test.ts
+++ b/src/hooks/todo-continuation-enforcer/todo-continuation-enforcer.test.ts
@@ -5,6 +5,7 @@ import { afterEach, beforeEach, describe, expect, test } from "bun:test"
 import type { BackgroundManager } from "../../features/background-agent"
 import { setMainSession, subagentSessions, _resetForTesting } from "../../features/claude-code-session-state"
 import { createTodoContinuationEnforcer } from "."
+import { CONTINUATION_COOLDOWN_MS } from "./constants"
 
 type TimerCallback = (...args: any[]) => void
 
@@ -507,6 +508,144 @@ describe("todo-continuation-enforcer", () => {
     expect(promptCalls).toHaveLength(0)
   })
 
+  test("should not inject again when cooldown is active", async () => {
+    //#given
+    const sessionID = "main-cooldown-active"
+    setupMainSessionWithBoulder(sessionID)
+    const hook = createTodoContinuationEnforcer(createMockPluginInput(), {})
+
+    //#when
+    await hook.handler({
+      event: { type: "session.idle", properties: { sessionID } },
+    })
+    await fakeTimers.advanceBy(2500, true)
+    await hook.handler({
+      event: { type: "session.idle", properties: { sessionID } },
+    })
+    await fakeTimers.advanceBy(2500, true)
+
+    //#then
+    expect(promptCalls).toHaveLength(1)
+  })
+
+  test("should inject again when cooldown expires", async () => {
+    //#given
+    const sessionID = "main-cooldown-expired"
+    setupMainSessionWithBoulder(sessionID)
+    const hook = createTodoContinuationEnforcer(createMockPluginInput(), {})
+
+    //#when
+    await hook.handler({
+      event: { type: "session.idle", properties: { sessionID } },
+    })
+    await fakeTimers.advanceBy(2500, true)
+    await fakeTimers.advanceBy(CONTINUATION_COOLDOWN_MS, true)
+    await hook.handler({
+      event: { type: "session.idle", properties: { sessionID } },
+    })
+    await fakeTimers.advanceBy(2500, true)
+
+    //#then
+    expect(promptCalls).toHaveLength(2)
+  })
+
+  test("should stop after stagnation cap and reset when todo hash changes", async () => {
+    //#given
+    const sessionID = "main-stagnation-cap"
+    setupMainSessionWithBoulder(sessionID)
+    let mutableTodoStatus: "pending" | "in_progress" = "pending"
+    const mockInput = createMockPluginInput()
+    mockInput.client.session.todo = async () => ({ data: [
+      { id: "1", content: "Task 1", status: mutableTodoStatus, priority: "high" },
+      { id: "2", content: "Task 2", status: "completed", priority: "medium" },
+    ]})
+    const hook = createTodoContinuationEnforcer(mockInput, {})
+
+    //#when
+    await hook.handler({ event: { type: "session.idle", properties: { sessionID } } })
+    await fakeTimers.advanceBy(2500, true)
+    await fakeTimers.advanceBy(CONTINUATION_COOLDOWN_MS, true)
+
+    await hook.handler({ event: { type: "session.idle", properties: { sessionID } } })
+    await fakeTimers.advanceBy(2500, true)
+    await fakeTimers.advanceBy(CONTINUATION_COOLDOWN_MS, true)
+
+    await hook.handler({ event: { type: "session.idle", properties: { sessionID } } })
+    await fakeTimers.advanceBy(2500, true)
+    await fakeTimers.advanceBy(CONTINUATION_COOLDOWN_MS, true)
+
+    await hook.handler({ event: { type: "session.idle", properties: { sessionID } } })
+    await fakeTimers.advanceBy(2500, true)
+
+    mutableTodoStatus = "in_progress"
+    await fakeTimers.advanceBy(CONTINUATION_COOLDOWN_MS, true)
+    await hook.handler({ event: { type: "session.idle", properties: { sessionID } } })
+    await fakeTimers.advanceBy(2500, true)
+
+    //#then
+    expect(promptCalls).toHaveLength(4)
+  })
+
+  test("should skip idle handling while injection is in flight", async () => {
+    //#given
+    const sessionID = "main-in-flight"
+    setupMainSessionWithBoulder(sessionID)
+    let resolvePrompt: (() => void) | undefined
+    const mockInput = createMockPluginInput()
+    mockInput.client.session.promptAsync = async (opts: any) => {
+      promptCalls.push({
+        sessionID: opts.path.id,
+        agent: opts.body.agent,
+        model: opts.body.model,
+        text: opts.body.parts[0].text,
+      })
+      await new Promise<void>((resolve) => {
+        resolvePrompt = resolve
+      })
+      return {}
+    }
+    const hook = createTodoContinuationEnforcer(mockInput, {})
+
+    //#when
+    await hook.handler({
+      event: { type: "session.idle", properties: { sessionID } },
+    })
+    await fakeTimers.advanceBy(2100, true)
+    await hook.handler({
+      event: { type: "session.idle", properties: { sessionID } },
+    })
+    await fakeTimers.advanceBy(3000, true)
+
+    //#then
+    expect(promptCalls).toHaveLength(1)
+
+    resolvePrompt?.()
+    await Promise.resolve()
+  })
+
+  test("should clear cooldown and stagnation state on session deleted", async () => {
+    //#given
+    const sessionID = "main-delete-state-reset"
+    setupMainSessionWithBoulder(sessionID)
+    const hook = createTodoContinuationEnforcer(createMockPluginInput(), {})
+
+    //#when
+    await hook.handler({
+      event: { type: "session.idle", properties: { sessionID } },
+    })
+    await fakeTimers.advanceBy(2500, true)
+    await hook.handler({
+      event: { type: "session.deleted", properties: { info: { id: sessionID } } },
+    })
+    await hook.handler({
+      event: { type: "session.idle", properties: { sessionID } },
+    })
+    await fakeTimers.advanceBy(2500, true)
+
+    //#then
+    expect(promptCalls).toHaveLength(2)
+  })
+
   test("should accept skipAgents option without error", async () => {
     // given - session with skipAgents configured for Prometheus
     const sessionID = "main-prometheus-option"
@@ -556,16 +695,16 @@ describe("todo-continuation-enforcer", () => {
     await hook.handler({
       event: { type: "session.idle", properties: { sessionID } },
     })
-    await fakeTimers.advanceBy(3500)
+    await fakeTimers.advanceBy(3500, true)
 
     // then - first injection happened
     expect(promptCalls.length).toBe(1)
 
-    // when - immediately trigger second idle (no 10s wait needed)
+    await fakeTimers.advanceBy(CONTINUATION_COOLDOWN_MS, true)
     await hook.handler({
       event: { type: "session.idle", properties: { sessionID } },
     })
-    await fakeTimers.advanceBy(3500)
+    await fakeTimers.advanceBy(3500, true)
 
     // then - second injection also happened (no throttle blocking)
     expect(promptCalls.length).toBe(2)
diff --git a/src/hooks/todo-continuation-enforcer/types.ts b/src/hooks/todo-continuation-enforcer/types.ts
index 8ef8745fa..c3384aa04 100644
--- a/src/hooks/todo-continuation-enforcer/types.ts
+++ b/src/hooks/todo-continuation-enforcer/types.ts
@@ -27,6 +27,10 @@ export interface SessionState {
   isRecovering?: boolean
   countdownStartedAt?: number
   abortDetectedAt?: number
+  lastInjectedAt?: number
+  inFlight?: boolean
+  lastTodoHash?: string
+  unchangedCycles?: number
 }
 
 export interface MessageInfo {