Apple mail drops password on reboot google

A frustrating issue!

When Apple Mail drops your password on reboot and you're using a Google account, it's likely due to a caching issue or a misconfiguration. Here are some troubleshooting steps to help you resolve the problem:

  1. Check your Google account settings:
    • Go to your Google Account settings (https://myaccount.google.com/) and ensure that "Less secure app access" is turned ON. This setting allows apps to access your account without two-factor authentication (2FA).
    • If you have 2FA enabled, you might need to generate an App Password (https://support.google.com/accounts/answer/185839) and use it in Apple Mail instead of your regular password.
  2. Clear Apple Mail's cache and data:
    • Quit Apple Mail.
    • Go to the Finder and navigate to ~/Library/Mail/V2/MailData.
    • Delete the Envelope Index and Mailbox Index files.
    • Restart Apple Mail.
  3. Reset Apple Mail's password cache:
    • Go to System Preferences > Internet Accounts.
    • Select your Google account and click the minus button (-) to remove it.
    • Then, click the "+" button to add your Google account again.
    • Enter your credentials, and Apple Mail should re-cache your password.
  4. Check your Apple Mail settings:
    • Go to System Preferences > Internet Accounts.
    • Select your Google account and click the "Edit" button.
    • Ensure that the "Password" field is not empty and that the password is correct.
  5. Try using a different email client:
    • If the issue persists, try using a different email client, such as Microsoft Outlook or Mozilla Thunderbird, to see if the problem is specific to Apple Mail.
  6. Reboot your Mac:
    • Sometimes, a simple reboot can resolve the issue.

If none of these steps resolve the problem, you can try resetting your Google account's password or seeking further assistance from Apple Support or Google Support.