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Every time I restart my Mac, my Keychain option in iCloud is unticked, my mail passwords are forgotten and my wallpaper goes into default.

Everyday, I fix it by checking the keychain and changing my wallpaper and fixing my mail passwords.

How can I get the Keychain to remain synchronized?

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It’s often a result of corrupted keychain files which can be fixed in three steps using Keychain Access first aid.

  1. Open "Keychain Access” (Applications > Utilities)
  2. Open the “Keychain Access” menu and choose “Keychain First Aid”
  3. Enter the users password and check the “Repair” box, then click “Start”

After keychain repairs are completed, exit out of Keychain Access and reboot. You may be asked one more time for the login, but from this point on it should remember it.

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  • Keychain First Aid was removed in macOS 10.11.2 and subsequent macOS versions. – DavidSupportsMonica May 16 '20 at 14:02

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