I'm trying to find possible places to look for an issue that I'm struggling with on my website. Scenario:

Ubuntu server uses sendmail and configured mail relay to go through our O365 servers. This was working on all environments 2 weeks ago, then stopped working on production only. To: is submitted to info@example.com and is also CC: to infodomain@gmail.com. The gmail.com contact form submissions come through without problems, but the example.com mailbox never receives the messages. IF, however, I send a test message from the web server to the example.com email address it is received in the mailbox.

It seemed odd to me that only one of the accounts are receiving the form, so I talked to my email admin and he's seeing the same consistency as the mailbox (so it doesn't appear to be a user issue on the mailbox).

At this point, it would all seem to point to the application configuration (WP) or a variation in the code or DB causing the issue - right? However, as one of the first steps in trying to resolve the issue, I did a backup from staging server (where the emails are working fine) and staging DB to push said snapshot into production (with literally the only thing changing in the process was a bulk-edit of the URL in the DB script).

What am I missing?

  • Problems like this are almost always caused by spam filters for me. – Stephen Ostermiller Jun 22 '17 at 20:32
  • I thought the same - or maybe a blacklisting issue. That's why I checked with the email admin to confirm what we were seeing with the messages - those messages were not appearing in the mail log. I'm torn between this being a server configuration issue (since it works on other servers with same code) and a code issue (since it is completely possible that somehow something was overlooked in the snapshot process - even though I've done it hundreds of times). – Dave Jun 22 '17 at 20:37
  • Rather than administering to your own e-mail system, have you considered the Mailgun API? It would solve issues like this right away. – L Martin Jun 23 '17 at 10:47
  • While this is an alternative solution, it doesn't help me diagnose my current problem. – Dave Jun 23 '17 at 19:03

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