#1537 new
Seth Talley

App Specific Passwords failing intermittently

Reported by Seth Talley | September 24th, 2016 @ 08:30 PM

I'm using app-specific passwords with gmail (and google for business with my own domain). mailmate has long been inconsistent and problematic (daily "sign in prevented" emails) but it now won't send at all.


I've tried revoking and resetting app passwords three times. I've tried restarting the computer. This is frustrating. Any suggestions?

Comments and changes to this ticket

  • benny

    benny September 25th, 2016 @ 06:08 AM

    As the error message describes then you need to log in via webmail to clear up the issue. Google has somehow flagged the access by IMAP as suspicious and they need you to log in to verify that everything is alright. Well, that's what they say.

    In general, using passwords with Google is getting harder and harder. You should go to the account editor (“File ▸ Edit IMAP Account ▸ ...”) and enable the OAuth2 checkmark (for both IMAP and SMTP). This is a different approach to logging in which is primarily designed for web-applications, but it can also be used by a desktop email client. If you are interested then I've written about the support in MailMate here.

  • Seth Talley

    Seth Talley September 25th, 2016 @ 04:11 PM

    Interesting. Logging in via webmail accomplished exactly nothing. In order to get it working again I needed to kill 2FA... but only for this one account, not the rest of the gmail accounts I'm syncing. So theoretically I can turn 2FA back on if I'm using OAuth2?

    I'm going to bounce your comments off Google and see what they come back with. They're not being helpful.

    Appreciate you looking into this,


  • benny

    benny September 25th, 2016 @ 09:26 PM

    I'm not quite sure what you are asking, but maybe this is the answer: If you use OAuth2 then you don't need an application specific password for MailMate.

    I don't know why one account would behave differently, but let me know if you think MailMate is somehow involved.

  • Seth Talley

    Seth Talley September 26th, 2016 @ 02:57 AM

    So unfortunately, Benny, it hangs upon wake. I have to quit Mailmate and re-open it in order to synchronize. Thoughts?

    Also, Lighthouse just told me I don't have permission to respond to your email.

  • benny

    benny September 26th, 2016 @ 07:18 AM

    And the other accounts do work with OAuth2?

    When it hangs, could you then run the following command from a Terminal window:

    sample MailMate 5 -f ~/Desktop/sample_mailmate.txt

    Then send me the resulting file (you can use “Help ▸ Send Feedback” if you like).

    Maybe also send me the following file to allow me to look for anything which might set this account apart:

    ~/Library/Application Support/MailMate/Sources.plist

    Lighthouse: Are you sure you sent from the same email address as you registered with Lighthouse?

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Mac OS X email client.

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