Outbound Apple Mail Gmail Messages Trapped in Outbox

When I upgraded from Snow Leopard to Mountain Lion I had a similar problem, but it only applied to sending mail, not receiving it.

I now have 4 application specific passwords for Mail in my keychain and Google account - one for IMAP for receiving mail and 3 for SMTP for sending mail. (To see your keychain, use Keychain Access - a utility in your Applications/Utilities folder.)

The trick I used is to not revoke the old passwords you've used - so if it asks for another password, keep the old ones for Mail on the Google account page (i.e. don't revoke) and then create another one.

I was revoking the old one before creating a new one and noticed in my keychain that different versions of the application specific password were applying to different ports. It looks like Mac Mail uses 3 ports by default for sending mail: 25, 465, 587.

As a result of seeing this, whenever it asked me for a new password, I created a new one, but stopped revoking the old one. I now have 3 Google SMTP passwords in my keychain for: "smtp://smtp.gmail.com", "smtp://smtp.gmail.com:465" and "smtp://smtp.gmail.com:587". It's been 3 days now, and so far so good, and up until I did this it had been going through a phase of constantly asking me.

I manually changed all 3 of SMTP the passwords to be the same in the keychain, but I doubt that that is necessary.

Possibly what happens is that Mail creates a password for one of the ports and then at some point it uses another port and wants a new password. By revoking the password for the other port, when it goes back to it again it asks for its password again. Maybe.

Does that work for you? This has been intermittent, so I can't be sure yet that this has fixed it.

I had the problem too and fixed it this way: revoke your app specific password and create a new one. Then copy it to the 'password' box for incoming mail server in mail / preferences / accounts / gmail. Then, and I think this is the key step, in the Outgoing Mail Server (SMTP) dropdown, select 'edit SMTP' server list. Click gmail, then go to Advanced pane. You have to add the same password here for the outgoing server.

I hope this helps, it appears to have worked for me.

This solved it for me, Thank you!!

As a Google Apps user (basically a corporate Google account), I tried all of those suggestions (and a few more). Turns out the solution was as simple as adding "@mydomain.com" to the default SMTP login username. So, instead of username "First.Lastname" in the SMTP editor it now reads "First.Lastname@mydomain.com".

Changing the port didn't seem to make a difference in my case.

Thanks! Worked like a charm!

This worked perfectly!!! I was receiving email perfectly fine, but Mail kept asking for my application-specific password to send. Changing it in the accounts settings didn't work. Thank so much!

BINGO!

Inside mail app, go to menu Mail -> Preferences -> Accounts -> Gmail. Then, select 'Edit SMTP Server List' from the 'Outgoing Mail Server (SMTP)' dropdown. Click gmail account, then go to Advanced pane... Here you should be sure that the @yourdomain.com is appended to your username. Be sure to add the same password here for the outgoing server.

Attention, Attention! Apple/Mac Mail developers... fix the code to use the fully qualified email address as the username in outgoing mail by default.

Attention, Attention! Apple/Mac Mail developers... fix the code to use the fully qualified email address as the username in outgoing mail by default.

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This worked perfectly for me! 🙂

Have been struggling with this for a while now....Worked like magic! Thank you!!

This solution worked perfectly for me. Thanks.

this does not work for me.

did not work as I've already had this. this happened recently. what a nightmare.