this post was submitted on 01 Feb 2026
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You're gonna have a bad time if you have to email MSFT/GOOG. MSFT was worse in my experience. their DumbScreen tech was horrible. Even the tech couldn't get my emails to not go to spam. Gave up in the end. The likes of MSFT and Google make it nigh on impossible for people to self host their own email.
Been running my own mailserve for last 20 years and never had big issues.
Do dkim dmark stuff and DNS records properly and you will be fine. Also don't spam and beware of spam-related subnets, and you should not have issues.
Have you considered that the reason why your mail server is trusted is because it's been around for 20 years?
Have you tried to set up mail from scratch on a new domain/ip recently?
I've been running my own email server for 15+ years. One year ago I needed to change VPS providers and thus get a totally different IP. I worried about this a bit, but actually had no issues whatsoever. Of course, I wasn't starting completely from scratch as I had the same domain, all my personal experience, and a battle-tested configuration for docker-mailserver. But yeah, the lack of IP reputation itself didn't seem to be an issue at all. Maybe I got lucky. Or maybe it's because I chose a relatively small Canadian VPS provider rather than one of the global cloud giants (I assume their IP address space gets pretty trashed with scammers).
What about domain reputation?