Gmail incorrectly flagging mail from new domain as spam

[Tiemo Kieft]

Hi,

I'm running into some problems with GMail's spam filter, it is flagging mail coming from my new domain as spam. The weird thing is that the exact same mail sent through the exact same SMTP server, but with a different domain, is not being flagged.

I have a detailed explanation up at Super User: https://superuser.com/questions/832749/some-mail-from-newly-setup-mailserver-flagged-spam-by-gmail

According to mxtoolbox.com my smtp server is set up correctly for both domains. Any help would be greatly appreciated!

[Marko Vukovic]

Hey Tiemo

How new are the domains, perhaps the DNS hasn't propagated properly yet and some lookup is failing. Have you tried sending other Gmail users email from both domains? Feel free to send me the test messages.

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Marko

[Tiemo Kieft]

Hi,

 

How new are the domains, perhaps the DNS hasn't propagated properly yet and some lookup is failing. Have you tried sending other Gmail users email from both domains? Feel free to send me the test messages.

The first domain, the one that the PTR for the IP is pointing at is well over 2 years old, the second domain is not even a week old, however, I recently switched to a new VPS, with a new IP address, that was around a week ago. I guess the DNS has propagated now, since its been a couple of days since the last change.

I ran both domains through the whole suite of tests at mxtoolbox.com again, and it indicates that everything is set up correctly, including DKIM, SPF and the PTR record, as well as TLS.

As far as I can tell everything is configured correctly, which leads me to believe that the problem might be with the IP address. Perhaps it's been used to send spam in the past.

In the mean time I also ran some more tests, just sending some non-suspicious content to various email addresses of people I know. GMail is not the only service flagging them as spam. At least Outlook.com is also doing it, but some other services don't. Especially private mailservers with spamassassin are not flagging them as spam.