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I'm trying to set up Apple Mail to send through my web host's SMTP server (not Gmail, or any common email provider), and as soon as I save the SMTP settings, Mail forgets the password, meaning that authentication always fails. I type the password in the dialog below, click OK, and then reopen the "Edit SMTP Servers" dialog, and the password is gone.

This seems to happen only for this SMTP account. Others work just fine. I've tried removing the password from Keychain, repairing Disk Permissions, and completely removing all of my Mail data, but Mail still forgets my password immediately. Authentication doesn't even succeed once.

How can I get Mail to remember my SMTP password? I'd rather not completely reset my Keychain, so I'm looking for any other suggestions.

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  • This might not be your issue, but if you are using two factor authentication (2FA) then you will find the password field blank for Google accounts it doesn't use a password in the usual sense. – unknowndomain Jul 15 '15 at 18:12
  • @unknowndomain It's not a 2FA account, but I wonder if Mail thinks it is. Is there a way to find out if thinks the account requires 2FA? – Joshua Dwire Jul 15 '15 at 19:18
  • I have had the exact same issue for a couple of weeks now. – mabartibin Aug 3 '15 at 7:57
  • Have you called Apple? – Daniel Springer Apr 25 '16 at 23:49
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I'm experiencing a similar issue. I've been doing some reading throughout the morning, and one possible solution I've found was covered here: http://osxdaily.com/2015/07/05/resolving-mail-problems-os-x-update/

Disabling 'automatically detect and maintain settings' seems to have cleared it up for me, however I'm not 100% sure that this will be your solution, as your screenshot shows that box already unchecked.

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I've seen this happen when the keychain file gets corrupted. From 10.9, the mail passwords are not stored in the normal login keychain, but in a host-specific database file (related to the iCloud keychain syncing; but, it happens even if you don't use iCloud).

In your ~/Library/Keychains/(UUID-UUID-UUID)/ directory, you may have a keychain2.db-corrupt file. (UUID is the UUID of the Mac you're using). If this is the case, restoring keychain2.db from a backup should fix your trouble.

  • better yet just remove the ~/Library/Keychains/U-U-I-D/ directory and all of its contents (after quitting all apps), and the immediately reboot. This procedure automatically re-creates the Local Items keychain, which seems to be manged by accountsd. This still works, and is sometimes still necessary in current macOS, up to and including 10.13.4. Also alway disable _'automatically detect and maintain settings' _ as it is extremely unreliable, even with a good internet connection and stable servers. – Greg A. Woods May 12 '18 at 5:51

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