diff --git a/src/main/claude/claude-structured-journal-prompt-retry.test.ts b/src/main/claude/claude-structured-journal-prompt-retry.test.ts
new file mode 100644
index 00000000000..9c7941f88bd
--- /dev/null
+++ b/src/main/claude/claude-structured-journal-prompt-retry.test.ts
@@ -0,0 +1,122 @@
+import { describe, expect, it } from 'vitest'
+import { agentJournalItemKey } from '../../shared/agent-session-journal-item-key'
+import type {
+  AgentJournalItemBody,
+  AgentJournalItemIdentity
+} from '../../shared/agent-session-journal-types'
+import type { StructuredAgentSessionEventSink } from '../native-chat/agent-session-wire/structured-agent-session-event-sink'
+import type { ClaudePendingPrompt } from './claude-structured-prompt-replies'
+import { createClaudeJournalTranslator } from './claude-structured-journal-translation'
+
+function approval(promptKey: string): ClaudePendingPrompt {
+  return {
+    requestId: promptKey,
+    promptKey,
+    toolUseId: 'tool-retry',
+    toolName: 'Bash',
+    kind: 'approval',
+    input: { command: 'git status' },
+    suggestions: [],
+    questionIds: [],
+    answers: new Map(),
+    settle: () => {}
+  }
+}
+
+function transientBackpressureSink(refusedAt: 'append' | 'publish'): {
+  sink: StructuredAgentSessionEventSink
+  durableApproval: () => AgentJournalItemBody | undefined
+  appendAttempts: () => number
+  publishAttempts: () => number
+  appliedSettlements: Set<string>
+} {
+  const staged = new Map<string, AgentJournalItemBody>()
+  const durable = new Map<string, AgentJournalItemBody>()
+  const appliedSettlements = new Set<string>()
+  let lifecycleAppendAttempts = 0
+  let lifecyclePublishAttempts = 0
+  const persist = (): void => {
+    durable.clear()
+    for (const [key, body] of staged) {
+      durable.set(key, body)
+    }
+  }
+  const applyItem = (identity: AgentJournalItemIdentity, body: AgentJournalItemBody): void => {
+    staged.set(agentJournalItemKey(identity), body)
+  }
+  return {
+    sink: {
+      appendItem: applyItem,
+      appendTombstone: (identity) => staged.delete(agentJournalItemKey(identity)),
+      publish: persist,
+      tryAppendLifecycleBatch: (settlementId, mutations) => {
+        lifecycleAppendAttempts += 1
+        if (refusedAt === 'append' && lifecycleAppendAttempts === 1) {
+          return { accepted: false, reason: 'backpressure' }
+        }
+        if (!appliedSettlements.has(settlementId)) {
+          for (const mutation of mutations) {
+            if (mutation.kind === 'item') {
+              applyItem(mutation.identity, mutation.body)
+            } else {
+              staged.delete(agentJournalItemKey(mutation.identity))
+            }
+          }
+          appliedSettlements.add(settlementId)
+        }
+        return { accepted: true }
+      },
+      tryPublish: () => {
+        lifecyclePublishAttempts += 1
+        if (refusedAt === 'publish' && lifecyclePublishAttempts === 1) {
+          return { accepted: false, reason: 'backpressure' }
+        }
+        persist()
+        return { accepted: true }
+      }
+    },
+    durableApproval: () => [...durable.values()].find((body) => body.kind === 'approval'),
+    appendAttempts: () => lifecycleAppendAttempts,
+    publishAttempts: () => lifecyclePublishAttempts,
+    appliedSettlements
+  }
+}
+
+describe('Claude journal prompt cancellation retry', () => {
+  it.each(['append', 'publish'] as const)(
+    'retries after transient lifecycle %s backpressure',
+    (refusedAt) => {
+      const state = transientBackpressureSink(refusedAt)
+      const translator = createClaudeJournalTranslator({ sink: state.sink })
+      const prompt = approval('permission-retry')
+
+      translator.handle({ type: 'prompt', sessionId: 'orca-session', prompt })
+      translator.handle({
+        type: 'prompt-cancelled',
+        sessionId: 'orca-session',
+        promptKey: prompt.promptKey
+      })
+      expect(state.durableApproval()).toMatchObject({ resolution: { state: 'pending' } })
+
+      translator.handle({
+        type: 'provider-frame',
+        sessionId: 'orca-session',
+        kind: 'control_request:retry-boundary',
+        payload: {}
+      })
+      expect(state.durableApproval()).toMatchObject({ resolution: { state: 'cancelled' } })
+      expect(state.appendAttempts()).toBe(2)
+      expect(state.publishAttempts()).toBe(refusedAt === 'publish' ? 2 : 1)
+      expect(state.appliedSettlements).toEqual(new Set(['prompt-cancelled:permission-retry']))
+
+      translator.handle({
+        type: 'provider-frame',
+        sessionId: 'orca-session',
+        kind: 'control_request:after-retry',
+        payload: {}
+      })
+      expect(state.appendAttempts()).toBe(2)
+      expect(state.publishAttempts()).toBe(refusedAt === 'publish' ? 2 : 1)
+    }
+  )
+})
diff --git a/src/main/claude/claude-structured-journal-prompts.ts b/src/main/claude/claude-structured-journal-prompts.ts
index 1860df0afe6..8d9d2c115a4 100644
--- a/src/main/claude/claude-structured-journal-prompts.ts
+++ b/src/main/claude/claude-structured-journal-prompts.ts
@@ -18,6 +18,7 @@ import {
 import type { ClaudeStructuredSessionEvent } from './claude-structured-session-state'
 
 const ADMITTED = { accepted: true } as const
+const MAX_PENDING_PROMPT_CANCELLATIONS = 64
 
 type ClaudeJournalPrompt = {
   identity: AgentJournalItemIdentity
@@ -36,11 +37,16 @@ function cancelledPromptBody(
 
 export class ClaudeJournalPrompts {
   private readonly items = new Map<string, ClaudeJournalPrompt[]>()
+  private readonly pendingCancellations = new Set<string>()
 
   get size(): number {
     return this.items.size
   }
 
+  get pendingCancellationCount(): number {
+    return this.pendingCancellations.size
+  }
+
   constructor(
     private readonly deps: {
       sink: StructuredAgentSessionEventSink
@@ -77,7 +83,7 @@ export class ClaudeJournalPrompts {
     this.deps.sink.publish()
   }
 
-  cancel(promptKey: string): StructuredAgentSessionSinkAdmission {
+  private admitCancellation(promptKey: string): StructuredAgentSessionSinkAdmission {
     const items = this.items.get(promptKey) ?? []
     if (items.length === 0) {
       return ADMITTED
@@ -125,11 +131,39 @@ export class ClaudeJournalPrompts {
     return published
   }
 
+  cancel(promptKey: string): StructuredAgentSessionSinkAdmission {
+    const admission = this.admitCancellation(promptKey)
+    if (admission.accepted || admission.reason !== 'backpressure') {
+      this.pendingCancellations.delete(promptKey)
+    } else if (
+      this.pendingCancellations.has(promptKey) ||
+      this.pendingCancellations.size < MAX_PENDING_PROMPT_CANCELLATIONS
+    ) {
+      this.pendingCancellations.add(promptKey)
+    }
+    return admission
+  }
+
+  retryPendingCancellations(): void {
+    if (this.pendingCancellations.size === 0) {
+      return
+    }
+    for (const promptKey of this.pendingCancellations) {
+      const admission = this.admitCancellation(promptKey)
+      if (!admission.accepted && admission.reason === 'backpressure') {
+        return
+      }
+      this.pendingCancellations.delete(promptKey)
+    }
+  }
+
   resolve(promptKey: string): void {
     this.items.delete(promptKey)
+    this.pendingCancellations.delete(promptKey)
   }
 
   clear(): void {
     this.items.clear()
+    this.pendingCancellations.clear()
   }
 }
diff --git a/src/main/claude/claude-structured-journal-translation.ts b/src/main/claude/claude-structured-journal-translation.ts
index c43ca316a50..b8a3c9fec49 100644
--- a/src/main/claude/claude-structured-journal-translation.ts
+++ b/src/main/claude/claude-structured-journal-translation.ts
@@ -255,6 +255,7 @@ export function createClaudeJournalTranslator(
 
   return {
     handle: (event) => {
+      prompts.retryPendingCancellations()
       if (event.type === 'ended') {
         streamedText.flush()
         // No event will ever settle a child once the provider is gone.
diff --git a/src/main/claude/claude-structured-prompt-ownership.test.ts b/src/main/claude/claude-structured-prompt-ownership.test.ts
index 1dd362ee856..f717a5063a0 100644
--- a/src/main/claude/claude-structured-prompt-ownership.test.ts
+++ b/src/main/claude/claude-structured-prompt-ownership.test.ts
@@ -702,4 +702,46 @@ describe('Claude live prompt ownership', () => {
     expect(tryAppendTombstone).not.toHaveBeenCalled()
     expect(tombstones).toEqual([])
   })
+
+  it('dedupes, bounds, and clears prompt cancellation retries', () => {
+    const prompts = new ClaudeJournalPrompts({
+      sink: {
+        appendItem: () => {},
+        appendTombstone: () => {},
+        publish: () => {},
+        tryAppendLifecycleBatch: () => ({ accepted: false, reason: 'backpressure' })
+      }
+    })
+    const registerCancellation = (index: number): void => {
+      const promptKey = `permission-${index}`
+      const prompt: ClaudePendingPrompt = {
+        requestId: promptKey,
+        promptKey,
+        toolUseId: `tool-${index}`,
+        toolName: 'Bash',
+        kind: 'approval',
+        input: { command: 'git status' },
+        suggestions: [],
+        questionIds: [],
+        answers: new Map(),
+        settle: vi.fn()
+      }
+      prompts.handle({ type: 'prompt', sessionId: 'session-1', prompt })
+      prompts.cancel(promptKey)
+    }
+
+    registerCancellation(0)
+    prompts.cancel('permission-0')
+    expect(prompts.pendingCancellationCount).toBe(1)
+    for (let index = 1; index < 65; index += 1) {
+      registerCancellation(index)
+    }
+    expect(prompts.pendingCancellationCount).toBe(64)
+
+    prompts.resolve('permission-0')
+    expect(prompts.pendingCancellationCount).toBe(63)
+    prompts.clear()
+    expect(prompts.pendingCancellationCount).toBe(0)
+    expect(prompts.size).toBe(0)
+  })
 })