Beware Google Mail/gmail External SMTP Feature

Last year, Google added a feature so that you could send authenticated email through another SMTP server.  This eliminated the need for the "on behalf of" Sender header.

It requires you to enter the authentication details of an account and it verifies that it can access the SMTP server at that time.

However, if that account changes (i.e. password change or anything which would cause authentication to fail), you will get no notification of email failures.  You can click send and the message will go into sent items, but will never arrive at the destination.  You will receive no bounce.  You will receive no message from Google that the account isn't working, there is no visual indication that anything is wrong.

Your mail will simply and silently not be sent.


  1. Cade,

    Thanks for the heads up. Part of the reason I transitioned to Google Apps for Your Domain a few years back was to avoid the "on behalf of" header. However, Google Apps seems to lag so far behind regular old Gmail that I'm considering forwarding everything from the domain back to the gmail.com account. Plus, I've had various and sundry miseries using the GAYD account from a few different mobile devices. Thanks for your thoughts on the matter.

  2. fescue - As far as I can tell, GAFYD is basically tracking GMail now if you have migrated your domain.

  3. Thanks Cade. Question - are you using Google Apps for your email fully, or do you forward the Apps mail over to Gmail? Just wondering what you found as the best solution. While Apps has many of the same features as Gmail now (and includes PicasaWeb, Blogger, etc), I still find myself using Apps for just mail and calendar, and the gmail address for everything else. thanks.

  4. fescue - I'm still in the process of moving everything over. My Apps account was a conflicting account, so I have to do a little- two-step to get that sorted out. My Google voice is still not transferred to it even though I requested it be transferred a while back. Also the Blogger accounts and other services are still a little screwy. Right now I have everything forward to gmail and I also have gmail pick up out of some mailboxes. I have still to transfer reader subscriptions and all my (many) rules. I have no idea how to transfer so much email. I also don't want to pay for a business domain since I have a bunch of family members on the domain.

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