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E-mails to Google Mail (@gmail.com) marked as spam

by on Feb.01, 2017, under Techie

I manage a private server that starting in late 2015 started having many of there e-mails for Invoice, Sign-ups, Lost Password Requests, or even support e-mail replies get put directly into the SPAM folder of the @gmail.com recipient with the notice of

“Why is this message in Spam? …” and some more about the content looking like it was spam (I have lost the exact wording).

In the past I had tried to adjust wording in the e-mail templates, but there are only so many ways to say what needed said. We have SPF, DKIM, and DMARC records which were soll perfect, but one thing was causing all of the problems. We also are only, currently, using IPv4 for e-mail. This server uses WHM/cPanel on the back-end and the site is WordPress/WooCommerce.

Cause: The sending server address was the main IP of the private server (X.X.A.X) vs. the static IP of the domains (X.X.C.X). Therefor the sending IPs PTR record didn’t match the domain the e-mail came from.
Fix: Change it so e-mail sent from a domain with a static IP (X.X.C.X) is also sent from that IP (X.X.C.X) vs. the servers default mail IP address (X.X.A.X).

  • Login to WHM
  • Click on Exim Configuration Manager (under the Service Configuration menu)
  • Click the Domains and IPs tab
  • Change “Send mail from account’s dedicated IP address” to On. The default (very stupid default IMO!) is Off.
  • Click Save at the bottom and Exim will restart

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