I tried maybe 15 years ago and it went about as well as you’d expect for back then. But I’m starting to get the itch again.
Have any of you tried relatively recently? How impossible is it to get reliable deliverability to gmail and whatnot these days?
The article’s answer to this one is handwavey “there are rules that spammers can’t meet, but you can do it just fine”. This is not the whole story by far. This is a more comprehensive overview of why it doesn’t work:
https://cfenollosa.com/blog/after-self-hosting-my-email-for-twenty-three-years-i-have-thrown-in-the-towel-the-oligopoly-has-won.html
On a dynamic IP connection, you can very easily have had the address flagged already. If the one you have now isn’t flagged, the one you get later might be. Debugging intermittent problems is not fun.
They also like it when your domain has shown good behavior already. I can do that because my domain has existed for over 20 years and I’ve hosted email on it in one form or another for that whole time. A person starting out on their own is not going to be able to do that.
This doesn’t necessarily mean that the big providers are the only option. There are smaller providers, like Fastmail.
Lastly, any server config where they claim it’s easy because “the configuration reads almost as plain english” is a big red flag for me. Plain language config or programming does not work as well as anyone thinks.
Never read this article before, thanks for sharing!