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Re:Dovecot audit complete by throwanem on Monday January 16, 2017 @05:59AM (#13409325)
If you're on DO or Linode or similar, you start with a new VPS and check the IP it's assigned in all the RBLs and spam blacklists. (Google "multi rbl check", there's a bunch.) If it's on any of them, tear down the VPS and stand up a fresh one, and repeat until you get a clean IP. Then keep it that way by not running an open relay.

Beyond that, the main deliverability improvements, in approximate order of value, are: PTR record with the hostname you send mail from; DKIM; SPF; DMARC.

My mail server runs all of these, and I've yet to encounter trouble sending to anyone, including Gmail, which is often mentioned in threads like these as being a special issue. Admittedly I've been running mail from that IP since 2004, so have a long history of not being a spammer, but as long as you start out with a clean IP and keep it so, and make sure all your sender legitimacy boxes are properly checked, I don't see any reason why you should have undue difficulty.

Re:Dovecot audit complete by throwanem on Monday January 16, 2017 @10:53AM (#13410623)
(That's approximate descending order of value, to be clear. In particular, if you don't have a matching PTR record, you're hosed whatever else you try to do.)
Re:Dovecot audit complete by greglindahl on Monday January 16, 2017 @01:42PM (#13411929)
Looking at the incoming mail in my server, I discovered that there are big legit mail senders who have a non-matching PTR. I suppose that at some point gmail et al stopped using that rule, or they just look for certain patterns in the PTR name, or something.