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Clarified that, at first, email can be both sent and received.
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Guy Gur-Ari
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I am using the Mail app on Mac OS X to access my Gmail account using 2-factor authentication. The app is configured with an application-specific password and it works fine for a few days: email can be sent and received without a problem. But then I get this error message:

The SMTP server "smtp.gmail.com" rejected the password for user "[email protected]"

From this point on no emails can be sent, although I still get incoming messages via IMAP.

If I revoke the app-specific password, generate a new one, and enter it in the app, it fixes the problem for a few days. Then I get this error again and must enter a new password. This has been going on for months.

Before I turned on 2-factor authentication, everything worked smoothly.

I also have Gmail configured on my iPhone with a different app-specific password, and there this problem does not occur.

I am using the Mail app on Mac OS X to access my Gmail account using 2-factor authentication. The app is configured with an application-specific password and it works fine for a few days. But then I get this error message:

The SMTP server "smtp.gmail.com" rejected the password for user "[email protected]"

From this point on no emails can be sent, although I still get incoming messages via IMAP.

If I revoke the app-specific password, generate a new one, and enter it in the app, it fixes the problem for a few days. Then I get this error again and must enter a new password. This has been going on for months.

Before I turned on 2-factor authentication, everything worked smoothly.

I also have Gmail configured on my iPhone with a different app-specific password, and there this problem does not occur.

I am using the Mail app on Mac OS X to access my Gmail account using 2-factor authentication. The app is configured with an application-specific password and it works fine for a few days: email can be sent and received without a problem. But then I get this error message:

The SMTP server "smtp.gmail.com" rejected the password for user "[email protected]"

From this point on no emails can be sent, although I still get incoming messages via IMAP.

If I revoke the app-specific password, generate a new one, and enter it in the app, it fixes the problem for a few days. Then I get this error again and must enter a new password. This has been going on for months.

Before I turned on 2-factor authentication, everything worked smoothly.

I also have Gmail configured on my iPhone with a different app-specific password, and there this problem does not occur.

Notice added Draw attention by Guy Gur-Ari
Bounty Started worth 50 reputation by Guy Gur-Ari
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Guy Gur-Ari
  • 339
  • 1
  • 3
  • 7

Gmail rejects SMTP password with 2-factor authentication

I am using the Mail app on Mac OS X to access my Gmail account using 2-factor authentication. The app is configured with an application-specific password and it works fine for a few days. But then I get this error message:

The SMTP server "smtp.gmail.com" rejected the password for user "[email protected]"

From this point on no emails can be sent, although I still get incoming messages via IMAP.

If I revoke the app-specific password, generate a new one, and enter it in the app, it fixes the problem for a few days. Then I get this error again and must enter a new password. This has been going on for months.

Before I turned on 2-factor authentication, everything worked smoothly.

I also have Gmail configured on my iPhone with a different app-specific password, and there this problem does not occur.