diff --git a/src/main/agent-hooks/installer-utils.ts b/src/main/agent-hooks/installer-utils.ts
index 5161da2cfa1..ae178a6eedf 100644
--- a/src/main/agent-hooks/installer-utils.ts
+++ b/src/main/agent-hooks/installer-utils.ts
@@ -216,6 +216,18 @@ function hookHasManagedCommand(hook: HookCommandConfig, matches: (value?: string
   return matches(hook.command) || args.some((arg) => typeof arg === 'string' && matches(arg))
 }
 
+// Users may opt a managed hook into async; keep that choice when the hook is rewritten.
+export function withPreviousManagedAsync(
+  hook: HookCommandConfig,
+  definitions: HookDefinition[],
+  matches: (command: string | undefined) => boolean
+): HookCommandConfig {
+  const async = definitions
+    .flatMap((definition) => (Array.isArray(definition.hooks) ? definition.hooks : []))
+    .find((prev) => typeof prev.async === 'boolean' && hookHasManagedCommand(prev, matches))?.async
+  return async === undefined ? hook : { ...hook, async }
+}
+
 export function hookDefinitionHasManagedCommand(
   definition: HookDefinition,
   isManagedCommand: (command: string | undefined) => boolean
diff --git a/src/main/claude/claude-hook-event-install.test.ts b/src/main/claude/claude-hook-event-install.test.ts
index 65ce8761e38..efcf3d1cea2 100644
--- a/src/main/claude/claude-hook-event-install.test.ts
+++ b/src/main/claude/claude-hook-event-install.test.ts
@@ -53,6 +53,37 @@ function expectUserSettingsKept(config: HooksConfig): void {
 }
 
 describe('Claude managed hook events by resolved version', () => {
+  it.each([true, false])(
+    'keeps a managed hook async=%s across reinstall and migration',
+    (async) => {
+      const userAsyncHook = { type: 'command' as const, command: 'echo user', async: !async }
+      const oldManagedHook = {
+        type: 'command' as const,
+        command: '/bin/sh',
+        args: ['/old/.orca/agent-hooks/claude-hook.sh'],
+        async
+      }
+      const written = install(
+        {
+          hooks: {
+            PreToolUse: [{ hooks: [userAsyncHook, oldManagedHook] }],
+            PostToolUse: [{ hooks: [userAsyncHook] }]
+          }
+        },
+        '2.1.32'
+      )
+      expect(written.hooks?.PreToolUse).toEqual([
+        { hooks: [userAsyncHook] },
+        { matcher: '*', hooks: [{ ...managedHook, async }] }
+      ])
+      expect(written.hooks?.PostToolUse).toEqual([
+        { hooks: [userAsyncHook] },
+        { matcher: '*', hooks: [managedHook] }
+      ])
+      expect(install(written, '2.1.32')).toEqual(written)
+    }
+  )
+
   it.each(Object.keys(enums))('writes only events Claude %s knows', (version) => {
     const written = install({ hooks: {} }, version)
     const unknown = Object.keys(written.hooks ?? {}).filter(
diff --git a/src/main/claude/hook-settings.ts b/src/main/claude/hook-settings.ts
index 7c8ce0a9573..edfc429d4b8 100644
--- a/src/main/claude/hook-settings.ts
+++ b/src/main/claude/hook-settings.ts
@@ -8,9 +8,9 @@ import {
   isSafeUnicodeWindowsBatchHookPath,
   MANAGED_HOOK_TIMEOUT_SECONDS,
   removeManagedCommands,
+  withPreviousManagedAsync,
   wrapWindowsPowerShellEncodedCommand,
   type HookCommandConfig,
-  type HookDefinition,
   type HooksConfig
 } from '../agent-hooks/installer-utils'
 import { quotePowerShellLiteral } from '../../shared/powershell-native-argument'
@@ -238,12 +238,10 @@ export function applyManagedHooks(
 
   for (const event of plan.install) {
     const current = nextHooks[event.eventName]
-    const cleaned = Array.isArray(current) ? removeManagedCommands(current, isManagedCommand) : []
-    const definition: HookDefinition = {
-      ...event.definition,
-      hooks: [hookForEvent(event.eventName)]
-    }
-    nextHooks[event.eventName] = [...cleaned, definition]
+    const previous = Array.isArray(current) ? current : []
+    const hook = withPreviousManagedAsync(hookForEvent(event.eventName), previous, isManagedCommand)
+    const cleaned = removeManagedCommands(previous, isManagedCommand)
+    nextHooks[event.eventName] = [...cleaned, { ...event.definition, hooks: [hook] }]
   }
 
   for (const event of plan.retire) {