Google now checking client-ip (jira server) against SPF records rather than configured MTA

Question

As of today our Google Apps account is reporting that emails coming from our JIRA Server instance are unable to be verified as coming from our domain. The setup is as follows (HOSTNAME:IP) ... MTA.TLD: 1.1.1.1 JIRA.TLD: 2.2.2.2 1.1.1.1 is in our SPF record and email from other clients using 1.1.1.1 as SMTP get delivered with no issues. When sending through JIRA with 1.1.1.1 configured as SMTP the SPF fails with the following Received: from MTA.TLD (MTA.TLD. [1.1.1.1]) by mx.google.com with ESMTPS id SOME_ID for (version=TLS1_2 cipher=ECDHE-RSA-AES128-GCM-SHA256 bits=128/128); Wed, 20 Jun 2018 07:30:14 -0700 (PDT) Received-SPF: fail (google.com: domain of jira@domain.com does not designate 2.2.2.2 as permitted sender) client-ip=2.2.2.2; Authentication-Results: mx.google.com; spf=fail (google.com: domain of jira@domain.com does not designate 2.2.2.2 as permitted sender) smtp.mailfrom=jira@domain.com Received: from JIRA.TLD (JIRA.TLD [2.2.2.2]) by MTA.TLD (Postfix) with ESMTP id SOME_ID for ; Wed, 20 Jun 2018 07:30:13 -0700 (MST) The only thing I could find about what might cause this is if the client is using it's own mail relay to send email to MTA.TLD, best I can tell from the SMTP logs when sending test emails this is not the case with JIRA but I'm not entirely sure. Does anyone know if this is the case or of something else that might be causing this validation error or for SPF validation to use the client-ip rather than the MTA ip?

Robert Jorgenson · Answer

Thanks for the response Mike. We are indeed using our own SMTP mail server and not google SMTP servers. Our initial quick fix is to add JIRA to our SPF record, but the JIRA server shouldn't be in our SPF record if it's a client and not actually delivering mail to our domain, which it's not. Worth noting that when sending mail from JIRA to non company domains like gmail.com the SPF uses the MTA address rather than the JIRA server IP and passes fine.

Mike Rathwell · Answer

Hi @Robert Jorgenson,

I ran into a variety of issues when we migrated from an in-house Exchange server to G-Suite. While what you're running into may be a PITA, it's probably a Good Thing from a security standpoint.

You may need to speak to your G-Suite admins about adding your host if it hasn't been already. I grepped Google and turned up this article: https://support.google.com/a/answer/33786

The other thing you may well run into, if your instance is of any size and activity, is G-Suite's hard limit of 2k messages per day through its SMTP server. If your MTA is sending out via G-Suite SMTP, this will eventually be a problem. We eventually just used another SMTP service (in our case, since I'm running in AWS, I just used AWS SES and configured that directly as the SMTP server.

Hope this gives at least some pointers to a solution. Good luck.

mike