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. 

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