Can't send emails using Google Apps Account with app specific password

First try the latest test version of MailMate: Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane. I don't really think it makes a different, but I need to be sure before doing further debugging.

Thanks for responding. I have Mailmate 3905. My Google Apps account still won't connect. Again, I am using an application specific password. It works fine in Mail.app. Also, when I imported my email accounts in Mailmate it did not import my iCloud account which I also wanted to import. I really like Mailmate and if I can get it to work for me I will buy it. I took to it immediately.

Thanks again.

You should get r4469 if you do as described: Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane.

Yes, iCloud accounts are not currently automatically imported since they are now stored differently by Apple Mail (there is no official API for doing this import). I should improve this, but for now you can do it manually using “File ▸ Add IMAP Account...” and the settings here.

OK. I downloaded the new version of Mailmate. I created a new app specific password and it worked. Then when I tried to send an email from my Google Apps account it did not go through and I got the following error message:

Unexpected return code 535 (expected 235):
“5.7.8 Username and Password not accepted. Learn more at 5.7.8 http://support.google.com/mail/bin/answer.py?answer=14257 h2sm2029026qah.35 - gsmtp”.

If I follow the link then it does look like Gmail is now blocking some email clients: https://support.google.com/accounts/answer/6010255

Could you try the advice described (allow less secure email clients). If it works then I'll research why Google thinks MailMate (and Outlook and Thunderbird) are insecure.

I tried that.
The Google pages states as follows:

"This setting is not available for Google Apps accounts, it is only available for Google Accounts." It looks like I can't use your app with my Google Apps account. The account works fine in Mail.app.

Thanks for trying. I'm still not sure exactly what limitations Google is implementing, but it's not being well received by the Thunderbird developers. Also, since you can login once then it may be a different issue (or a MailMate bug).

I would also expect more reports about this issue if all Google Apps users have the same issue. Is your account recently created or is it an old one?

We can take MailMate out of the equation by using the Terminal window to log in:

openssl s_client -connect imap.gmail.com:993 -crlf

Then when prompt is shown:

0 login you@example.com password

With your email address and application specific password.

To logout nicely:

0 logout

You can then also test if you can do this twice.

I am not sure what to do. My plan is to move from Gmail to Fastmail. Maybe I will just use Mailmate with Fastmail and use Gmail on the web if I need it. I have already imported all my Gmails into Fastmail.

Any thoughts?

The terminial thing is too technical for me. Makes me nervous.

My Google Apps account is over a year old.

If you wouldn't mind, may I ask if there is email provider you would recommend over Fastmail? You know a lot more about email than I do :).

Fastmail is a good choice. I wrote about alternatives here.

Quick data point, I am using an app specific password with google apps (for business) without issue. Happy to check anything else that might be a variable.

@Jon: Thanks. It'll be fine if you can just enable “watching” this ticket such that you are notified if more users show up with the same problem as David.

With respect to an alternative login method for Gmail. I've looked into it and maybe it won't be as hard to implement as I first thought, but I haven't actually tried yet.

I'm also using an app-specific password with Google Apps (for business). It's been working without problems, and I try to keep up with the latest dev releases.

@Evans: Thanks for the data point. It is not impossible that users see different behavior, because apparently Google has introduced a system for regular accounts where the default settings depend on whether or not the user accesses an account via IMAP within 30 days of creating the account. Maybe something similar is true for Google Apps.

A first attempt to support OAuth 2.0 for Gmail is part of the latest test release: Hold down ⌥ when clicking “Check Now” in the Software Update preferences pane. See the release notes for instructions on how to enable this feature.

I may have found a workaround for this issue. I have two gmail accounts set-up and I noticed that the SMTP app-specific password failure only occurred on one of them. When I compared account set-ups the working account had smtp.gmail.com as the SMTP server, while the failing account had smtp.googlemail.com. I changed the SMTP server to smtp.gmail.com for both accounts and I haven't had a problem in ~24 hours (the problem was happening every two or three hours before the change).