User profile for user: yerg
yerg Author
User level: Level 1
9 points

App-specific password fails on MacBook Air after shutdown

  • I set up an app specific password
  • That password works just fine

UNTIL

  • I switch off my MacBook Air
  • App specific password fails and I need to create a new one


If I "sleep" the Air all is ok.


How to best resolve, this is getting past a joke

MacBook Air 13″, macOS 11.7

Posted on Nov 29, 2025 6:57 PM

Reply
Question marked as Top-ranking reply
User profile for user: azaksalmarzur28
azaksalmarzur28
User level: Level 4
1,930 points

Posted on Dec 8, 2025 2:59 AM

Reset your Login Keychain (most reliable)

If the login.keychain file is damaged — this is common on Big Sur — it will not unlock early enough during boot.

Steps:

  1. Open Keychain Access
  2. Click File → New Keychain…
  3. Name it login (this replaces the old login keychain)
  4. Set a password that matches your Mac login password
  5. Reboot
  6. Re-enter your app-specific password in your email or app settings


Now the keychain loads cleanly at boot, and the password persists across shutdowns.

View in context

Similar questions

1 reply
Question marked as Top-ranking reply
User profile for user: azaksalmarzur28
azaksalmarzur28
User level: Level 4
1,930 points

Dec 8, 2025 2:59 AM in response to yerg

Reset your Login Keychain (most reliable)

If the login.keychain file is damaged — this is common on Big Sur — it will not unlock early enough during boot.

Steps:

  1. Open Keychain Access
  2. Click File → New Keychain…
  3. Name it login (this replaces the old login keychain)
  4. Set a password that matches your Mac login password
  5. Reboot
  6. Re-enter your app-specific password in your email or app settings


Now the keychain loads cleanly at boot, and the password persists across shutdowns.

Reply

This thread has been closed by the system or the community team. You may vote for any posts you find helpful, or search the Community for additional answers.

App-specific password fails on MacBook Air after shutdown

Welcome to Apple Support Community
A forum where Apple customers help each other with their products. Get started with your Apple Account.
Learn more Sign up