diff --git a/src/components/permissions/MonitorPermissionRequest/MonitorPermissionRequest.test.tsx b/src/components/permissions/MonitorPermissionRequest/MonitorPermissionRequest.test.tsx
new file mode 100644
index 000000000..e4024d6a6
--- /dev/null
+++ b/src/components/permissions/MonitorPermissionRequest/MonitorPermissionRequest.test.tsx
@@ -0,0 +1,509 @@
+import { PassThrough } from 'node:stream'
+import { mkdtempSync, rmSync } from 'node:fs'
+import { join } from 'node:path'
+import { tmpdir } from 'node:os'
+
+import { afterEach, beforeEach, describe, expect, mock, test } from 'bun:test'
+import React from 'react'
+import stripAnsi from 'strip-ansi'
+
+import { getOriginalCwd, setOriginalCwd } from '../../../bootstrap/state.js'
+import { handleInteractivePermission } from '../../../hooks/toolPermission/handlers/interactiveHandler.js'
+import { createPermissionContext } from '../../../hooks/toolPermission/PermissionContext.js'
+import { createRoot } from '../../../ink.js'
+import { DEFAULT_BINDINGS } from '../../../keybindings/defaultBindings.js'
+import { KeybindingProvider } from '../../../keybindings/KeybindingContext.js'
+import { parseBindings } from '../../../keybindings/parser.js'
+import {
+  acquireSharedMutationLock,
+  releaseSharedMutationLock,
+} from '../../../test/sharedMutationLock.js'
+import type {
+  KeybindingContextName,
+  ParsedKeystroke,
+} from '../../../keybindings/types.js'
+import {
+  getDefaultAppState,
+  type AppState,
+} from '../../../state/AppStateStore.js'
+import type { ToolUseContext } from '../../../Tool.js'
+import { MonitorTool } from '../../../tools/MonitorTool/MonitorTool.js'
+import type {
+  PermissionAllowDecision,
+  PermissionDecision,
+} from '../../../utils/permissions/PermissionResult.js'
+import type { PermissionUpdate } from '../../../utils/permissions/PermissionUpdateSchema.js'
+import type { ToolUseConfirm } from '../PermissionRequest.js'
+
+function createTestStreams(): {
+  stdout: PassThrough
+  stdin: PassThrough & {
+    isTTY: boolean
+    setRawMode: (mode: boolean) => void
+    ref: () => void
+    unref: () => void
+  }
+  getOutput: () => string
+} {
+  let output = ''
+  const stdout = new PassThrough()
+  const stdin = new PassThrough() as PassThrough & {
+    isTTY: boolean
+    setRawMode: (mode: boolean) => void
+    ref: () => void
+    unref: () => void
+  }
+
+  stdin.isTTY = true
+  stdin.setRawMode = () => {}
+  stdin.ref = () => {}
+  stdin.unref = () => {}
+  ;(stdout as unknown as { columns: number }).columns = 120
+  stdout.on('data', chunk => {
+    output += chunk.toString()
+  })
+
+  return {
+    stdout,
+    stdin,
+    getOutput: () => output,
+  }
+}
+
+async function waitFor(
+  predicate: () => boolean,
+  timeoutMs = 1000,
+): Promise<void> {
+  const startedAt = Date.now()
+
+  while (Date.now() - startedAt < timeoutMs) {
+    if (predicate()) return
+    await Bun.sleep(10)
+  }
+
+  throw new Error('Timed out waiting for Monitor permission test condition')
+}
+
+function expectAllowDecision(
+  decision: PermissionDecision,
+): asserts decision is PermissionAllowDecision {
+  expect(decision.behavior).toBe('allow')
+  if (decision.behavior !== 'allow') {
+    throw new Error(`Expected allow decision, received ${decision.behavior}`)
+  }
+}
+
+function createToolUseConfirm(
+  overrides: Partial<ToolUseConfirm> = {},
+): ToolUseConfirm {
+  return {
+    assistantMessage: {
+      type: 'assistant',
+      uuid: 'assistant-uuid',
+      message: {
+        id: 'msg_123',
+        type: 'message',
+        role: 'assistant',
+        content: [],
+        model: 'test-model',
+        stop_reason: null,
+        stop_sequence: null,
+        usage: {
+          input_tokens: 0,
+          output_tokens: 0,
+        },
+      },
+    },
+    tool: MonitorTool,
+    description: 'watch log',
+    input: {
+      command: 'tail -f app.log',
+      description: 'watch log',
+    },
+    toolUseContext: {} as ToolUseConfirm['toolUseContext'],
+    toolUseID: 'toolu_monitor',
+    permissionResult: {
+      behavior: 'ask',
+      message: 'Permission required',
+    },
+    permissionPromptStartTimeMs: Date.now(),
+    onUserInteraction: mock(() => {}),
+    onAbort: mock(() => {}),
+    onAllow: mock(() => {}),
+    onReject: mock(() => {}),
+    recheckPermission: mock(async () => {}),
+    ...overrides,
+  }
+}
+
+function createToolUseContext(): {
+  toolUseContext: ToolUseContext
+} {
+  let appState = getDefaultAppState()
+
+  const toolUseContext = {
+    options: {
+      commands: [],
+      debug: false,
+      mainLoopModel: 'test-model',
+      tools: [MonitorTool],
+      verbose: false,
+      thinkingConfig: {},
+      mcpClients: [],
+      mcpResources: {},
+      isNonInteractiveSession: false,
+      agentDefinitions: { activeAgents: [], allAgents: [] },
+    },
+    abortController: new AbortController(),
+    readFileState: {},
+    messages: [],
+    getAppState: () => appState,
+    setAppState: (updater: (prev: AppState) => AppState) => {
+      appState = updater(appState)
+    },
+    setInProgressToolUseIDs: () => {},
+    setResponseLength: () => {},
+    updateFileHistoryState: () => {},
+    updateAttributionState: () => {},
+  } as unknown as ToolUseContext
+
+  return {
+    toolUseContext,
+  }
+}
+
+function createInteractiveMonitorPermission(): {
+  toolUseConfirm: ToolUseConfirm
+  toolUseContext: ToolUseContext
+  decisionPromise: Promise<PermissionDecision>
+} {
+  const { toolUseContext } = createToolUseContext()
+  const base = createToolUseConfirm({ toolUseContext })
+  let queue: ToolUseConfirm[] = []
+
+  const ctx = createPermissionContext(
+    MonitorTool,
+    base.input,
+    toolUseContext,
+    base.assistantMessage,
+    base.toolUseID,
+    toolPermissionContext => {
+      toolUseContext.setAppState(prev => ({
+        ...prev,
+        toolPermissionContext,
+      }))
+    },
+    {
+      push(item) {
+        queue = [...queue, item]
+      },
+      remove(toolUseID) {
+        queue = queue.filter(item => item.toolUseID !== toolUseID)
+      },
+      update(toolUseID, patch) {
+        queue = queue.map(item =>
+          item.toolUseID === toolUseID ? { ...item, ...patch } : item,
+        )
+      },
+    },
+  )
+
+  const decisionPromise = new Promise<PermissionDecision>(resolve => {
+    handleInteractivePermission(
+      {
+        ctx,
+        description: base.description,
+        result: base.permissionResult as PermissionDecision & {
+          behavior: 'ask'
+        },
+        awaitAutomatedChecksBeforeDialog: true,
+      },
+      resolve,
+    )
+  })
+
+  if (!queue[0]) {
+    throw new Error('Expected handleInteractivePermission to queue a prompt')
+  }
+
+  return {
+    toolUseConfirm: queue[0],
+    toolUseContext,
+    decisionPromise,
+  }
+}
+
+function TestKeybindingProvider({
+  children,
+}: {
+  children: React.ReactNode
+}): React.ReactNode {
+  const bindings = React.useMemo(() => parseBindings(DEFAULT_BINDINGS), [])
+  const pendingChordRef = React.useRef<ParsedKeystroke[] | null>(null)
+  const [pendingChord, setPendingChordState] = React.useState<
+    ParsedKeystroke[] | null
+  >(null)
+  const activeContextsRef = React.useRef<Set<KeybindingContextName>>(new Set())
+  const handlerRegistryRef = React.useRef(
+    new Map<
+      string,
+      Set<{
+        action: string
+        context: KeybindingContextName
+        handler: () => void
+      }>
+    >(),
+  )
+
+  const setPendingChord = React.useCallback(
+    (pending: ParsedKeystroke[] | null) => {
+      pendingChordRef.current = pending
+      setPendingChordState(pending)
+    },
+    [],
+  )
+
+  const registerActiveContext = React.useCallback(
+    (context: KeybindingContextName) => {
+      activeContextsRef.current.add(context)
+    },
+    [],
+  )
+
+  const unregisterActiveContext = React.useCallback(
+    (context: KeybindingContextName) => {
+      activeContextsRef.current.delete(context)
+    },
+    [],
+  )
+
+  return (
+    <KeybindingProvider
+      bindings={bindings}
+      pendingChordRef={pendingChordRef}
+      pendingChord={pendingChord}
+      setPendingChord={setPendingChord}
+      activeContexts={activeContextsRef.current}
+      registerActiveContext={registerActiveContext}
+      unregisterActiveContext={unregisterActiveContext}
+      handlerRegistryRef={handlerRegistryRef}
+    >
+      {children}
+    </KeybindingProvider>
+  )
+}
+
+async function renderMonitorPermission(
+  toolUseConfirm: ToolUseConfirm,
+  callbacks: {
+    onDone?: () => void
+    onReject?: () => void
+  } = {},
+): Promise<{
+  stdin: ReturnType<typeof createTestStreams>['stdin']
+  cleanup: () => void
+}> {
+  const { stdout, stdin, getOutput } = createTestStreams()
+  const { AppStateProvider } = await import('../../../state/AppState.js')
+  const { MonitorPermissionRequest } = await import(
+    './MonitorPermissionRequest.js'
+  )
+  const root = await createRoot({
+    stdout: stdout as unknown as NodeJS.WriteStream,
+    stdin: stdin as unknown as NodeJS.ReadStream,
+    patchConsole: false,
+  })
+
+  root.render(
+    <AppStateProvider>
+      <TestKeybindingProvider>
+        <MonitorPermissionRequest
+          toolUseConfirm={toolUseConfirm}
+          toolUseContext={toolUseConfirm.toolUseContext}
+          onDone={callbacks.onDone ?? (() => {})}
+          onReject={callbacks.onReject ?? (() => {})}
+          verbose={false}
+          workerBadge={undefined}
+        />
+      </TestKeybindingProvider>
+    </AppStateProvider>,
+  )
+
+  await waitFor(() =>
+    stripAnsi(getOutput()).includes('Do you want to proceed?'),
+  )
+
+  return {
+    stdin,
+    cleanup: () => {
+      root.unmount()
+      stdin.end()
+      stdout.end()
+    },
+  }
+}
+
+beforeEach(async () => {
+  await acquireSharedMutationLock(
+    'components/permissions/MonitorPermissionRequest.test.tsx',
+  )
+  mock.module('../PermissionRuleExplanation.js', () => ({
+    PermissionRuleExplanation: () => null,
+  }))
+})
+
+afterEach(() => {
+  try {
+    mock.restore()
+  } finally {
+    releaseSharedMutationLock()
+  }
+})
+
+describe('MonitorPermissionRequest', () => {
+  test('allow once resolves the real pending permission promise and closes the dialog', async () => {
+    const onDone = mock(() => {})
+    const { toolUseConfirm, decisionPromise } =
+      createInteractiveMonitorPermission()
+    const mounted = await renderMonitorPermission(toolUseConfirm, { onDone })
+
+    try {
+      mounted.stdin.write('\r')
+
+      await waitFor(() => onDone.mock.calls.length === 1)
+      const decision = await decisionPromise
+
+      expectAllowDecision(decision)
+      expect(decision.updatedInput).toEqual(toolUseConfirm.input)
+    } finally {
+      mounted.cleanup()
+    }
+  })
+
+  test('allow persistently resolves the permission with a Bash allow rule and closes the dialog', async () => {
+    const onDone = mock(() => {})
+    const toolUseConfirm = createToolUseConfirm()
+    const mounted = await renderMonitorPermission(toolUseConfirm, { onDone })
+
+    try {
+      mounted.stdin.write('2')
+
+      await waitFor(() => onDone.mock.calls.length === 1)
+
+      expect(toolUseConfirm.onAllow).toHaveBeenCalledWith(
+        toolUseConfirm.input,
+        [
+          {
+            type: 'addRules',
+            rules: [{ toolName: 'Bash', ruleContent: 'tail -f:*' }],
+            behavior: 'allow',
+            destination: 'localSettings',
+          },
+        ],
+      )
+      expect(toolUseConfirm.onReject).not.toHaveBeenCalled()
+    } finally {
+      mounted.cleanup()
+    }
+  })
+
+  test('rendered persistent allow resolves the real pending permission promise with a Bash allow rule', async () => {
+    const originalCwd = getOriginalCwd()
+    const tempCwd = mkdtempSync(join(tmpdir(), 'monitor-permission-'))
+    const onDone = mock(() => {})
+
+    setOriginalCwd(tempCwd)
+    const { toolUseConfirm, toolUseContext, decisionPromise } =
+      createInteractiveMonitorPermission()
+    const mounted = await renderMonitorPermission(toolUseConfirm, { onDone })
+
+    try {
+      mounted.stdin.write('2')
+
+      await waitFor(() => onDone.mock.calls.length === 1)
+      const decision = await decisionPromise
+
+      expectAllowDecision(decision)
+      expect(decision.updatedInput).toEqual(toolUseConfirm.input)
+      expect(
+        toolUseContext.getAppState().toolPermissionContext.alwaysAllowRules
+          .localSettings,
+      ).toContain('Bash(tail -f:*)')
+    } finally {
+      mounted.cleanup()
+      setOriginalCwd(originalCwd)
+      rmSync(tempCwd, { recursive: true, force: true })
+    }
+  })
+
+  test('permission continuation resolves when approval includes permission updates', async () => {
+    const { toolUseConfirm, toolUseContext, decisionPromise } =
+      createInteractiveMonitorPermission()
+    const permissionUpdates: PermissionUpdate[] = [
+      {
+        type: 'addRules',
+        rules: [{ toolName: 'Bash', ruleContent: 'tail -f:*' }],
+        behavior: 'allow',
+        destination: 'session',
+      },
+    ]
+
+    toolUseConfirm.onAllow(toolUseConfirm.input, permissionUpdates)
+    const decision = await decisionPromise
+
+    expectAllowDecision(decision)
+    expect(decision.updatedInput).toEqual(toolUseConfirm.input)
+    expect(
+      toolUseContext.getAppState().toolPermissionContext.alwaysAllowRules
+        .session,
+    ).toContain('Bash(tail -f:*)')
+  })
+
+  test('deny resolves rejection, runs the reject continuation, and closes the dialog', async () => {
+    const onDone = mock(() => {})
+    const onReject = mock(() => {})
+    const { toolUseConfirm, toolUseContext, decisionPromise } =
+      createInteractiveMonitorPermission()
+    const mounted = await renderMonitorPermission(toolUseConfirm, {
+      onDone,
+      onReject,
+    })
+
+    try {
+      mounted.stdin.write('3')
+
+      await waitFor(() => onDone.mock.calls.length === 1)
+      const decision = await decisionPromise
+
+      expect(decision.behavior).toBe('ask')
+      expect(toolUseContext.abortController.signal.aborted).toBe(true)
+      expect(onReject).toHaveBeenCalledTimes(1)
+    } finally {
+      mounted.cleanup()
+    }
+  })
+
+  test('escape cancels the pending permission request and closes the dialog', async () => {
+    const onDone = mock(() => {})
+    const onReject = mock(() => {})
+    const { toolUseConfirm, toolUseContext, decisionPromise } =
+      createInteractiveMonitorPermission()
+    const mounted = await renderMonitorPermission(toolUseConfirm, {
+      onDone,
+      onReject,
+    })
+
+    try {
+      mounted.stdin.write('\u001B')
+
+      await waitFor(() => onDone.mock.calls.length === 1)
+      const decision = await decisionPromise
+
+      expect(decision.behavior).toBe('ask')
+      expect(toolUseContext.abortController.signal.aborted).toBe(true)
+      expect(onReject).toHaveBeenCalledTimes(1)
+    } finally {
+      mounted.cleanup()
+    }
+  })
+})
diff --git a/src/components/permissions/MonitorPermissionRequest/MonitorPermissionRequest.tsx b/src/components/permissions/MonitorPermissionRequest/MonitorPermissionRequest.tsx
index eb8243d00..4a892e3a8 100644
--- a/src/components/permissions/MonitorPermissionRequest/MonitorPermissionRequest.tsx
+++ b/src/components/permissions/MonitorPermissionRequest/MonitorPermissionRequest.tsx
@@ -2,7 +2,7 @@ import React from 'react'
 import { getOriginalCwd } from '../../../bootstrap/state.js'
 import { Box, Text } from '../../../ink.js'
 import { sanitizeToolNameForAnalytics } from '../../../services/analytics/metadata.js'
-import { env } from '../../../utils/env.js'
+import type { PermissionUpdate } from '../../../utils/permissions/PermissionUpdateSchema.js'
 import { shouldShowAlwaysAllowOptions } from '../../../utils/permissions/permissionsLoader.js'
 import { usePermissionRequestLogging } from '../hooks.js'
 import { PermissionDialog } from '../PermissionDialog.js'
@@ -38,56 +38,40 @@ export function MonitorPermissionRequest({
   ) => {
     switch (value) {
       case 'yes': {
-        logUnaryPermissionEvent({
-          completion_type: 'tool_use_single',
-          event: 'accept',
-          metadata: {
-            language_name: 'none',
-            message_id: toolUseConfirm.assistantMessage.message.id,
-            platform: env.platform,
-          },
-        })
+        logUnaryPermissionEvent('tool_use_single', toolUseConfirm, 'accept')
         toolUseConfirm.onAllow(toolUseConfirm.input, [], feedback)
         onDone()
         break
       }
       case 'yes-dont-ask-again': {
-        logUnaryPermissionEvent({
-          completion_type: 'tool_use_single',
-          event: 'accept',
-          metadata: {
-            language_name: 'none',
-            message_id: toolUseConfirm.assistantMessage.message.id,
-            platform: env.platform,
-          },
-        })
+        logUnaryPermissionEvent('tool_use_single', toolUseConfirm, 'accept')
         // Save the rule under 'Bash' toolName because checkPermissions
         // delegates to bashToolHasPermission which matches rules against
         // BashTool. Using 'Monitor' here would create a rule that's never
         // checked. Command-specific prefix (like BashTool's shellRuleMatching).
         const cmdForRule = command?.trim() || ''
         const prefix = cmdForRule.split(/\s+/).slice(0, 2).join(' ')
-        toolUseConfirm.onAllow(toolUseConfirm.input, prefix ? [
-          {
-            type: 'addRules',
-            rules: [{ toolName: 'Bash', ruleContent: `${prefix}:*` }],
-            behavior: 'allow',
-            destination: 'localSettings',
-          },
-        ] : [])
+        const permissionUpdates: PermissionUpdate[] = prefix
+          ? [
+              {
+                type: 'addRules',
+                rules: [{ toolName: 'Bash', ruleContent: `${prefix}:*` }],
+                behavior: 'allow',
+                destination: 'localSettings',
+              },
+            ]
+          : []
+        toolUseConfirm.onAllow(toolUseConfirm.input, permissionUpdates)
         onDone()
         break
       }
       case 'no': {
-        logUnaryPermissionEvent({
-          completion_type: 'tool_use_single',
-          event: 'reject',
-          metadata: {
-            language_name: 'none',
-            message_id: toolUseConfirm.assistantMessage.message.id,
-            platform: env.platform,
-          },
-        })
+        logUnaryPermissionEvent(
+          'tool_use_single',
+          toolUseConfirm,
+          'reject',
+          !!feedback?.trim(),
+        )
         toolUseConfirm.onReject(feedback)
         onReject()
         onDone()
@@ -97,15 +81,7 @@ export function MonitorPermissionRequest({
   }
 
   const handleCancel = () => {
-    logUnaryPermissionEvent({
-      completion_type: 'tool_use_single',
-      event: 'reject',
-      metadata: {
-        language_name: 'none',
-        message_id: toolUseConfirm.assistantMessage.message.id,
-        platform: env.platform,
-      },
-    })
+    logUnaryPermissionEvent('tool_use_single', toolUseConfirm, 'reject')
     toolUseConfirm.onReject()
     onReject()
     onDone()