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?
To be honest it's mostly FUD. Self host email is perfectly doable provided that:
What happened to me over the years was having the subnet my ip was is being associated to spammers, and that was a problem. It took several iterations with blacklists and my provider to get it sorted. That's why I recommend using a reputable service provider that take care of spammers in a timely manner.
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?
Yes, I migrated IP (from one provided to another) last year, and I recently added a new domain as well.
The new domain on the new ip just works, and the old domain on the same new ip just keep working.
Both the old and new ip are not residential IPs, I rent a small dedicated server for this purpose on the major hoster of my country. I pay about 15€/month for that, but it's not only used for email, for all my services.
So I've been setting up Stalwart (but I probably won't be using it), and I only had to unflag my emails as spam on Gmail and Outlook once; it even was able to send straight to the inbox of another Gmail account! I did have one email get quarantined by Outlook, but it was probably because the email and sender name didn't match enough.