Solved: Gmail bouncing messages

Over the weekend I was plagued with Gmail bouncing messages. The message was

SMTP error from remote mail server after end of data: [IP address] Our system has detected that this message is suspicious due to the nature of the content and/or the links within. To best protect our users from spam, the message has been blocked. Please visit for more information. q91si6161949pja.149 - gsmtp

Eventually I worked out that the message included links to and this is a url shortening service which presumably Gmail doesn’t like because the eventual destination of the link is hidden. When I changed the links to the final destination the emails went through. Mind, I had to delete lines from the usermessage table so the message was sent again to the gmail addresses when I requeued it.


That’s interesting, although fairly annoying that they would block a message just for using a link shortener, considering how those are widely used and in some cases necessary. That service even has a preview feature, as does Bitly and I assume others as well (though presumably not all).

I think this speaks to the general disregard for bulk email, even when the recipients clearly asked for and want it. It’s easier to just take a blunt approach to things and not worry about the valid email that’s being blocked than to make an effort to not throw out the baby with the bath water.