I'm learning so much about how much of a pain in the ass it is to run your own mail server.

Still, also don't know how/why tf do I still do it.

@ryan I gave up on that years ago. Practically it's an oligopoly with lots of manual work as the price of entry IMHO.

@J12t I actually have been using hmailserver for many years, but recently discovered a really rare/annoying bug caused by quirks between the host and a couple mail clients (different combinations behaved differently). I decided to ditch hmailserver and try mail in a box (postfix/dovecot/etc) and it seems much more stable across clients.

@ryan I go through this same exercise every 3 or 4 years and eventually go back to using a hosting provider. I think it's a great skill to have and to understand how to secure it properly.

I've been hosting my own email for over 5 years now, most recently, and other than dealing with some Microsoft domains, it is a set it and forget it kind of thing. Updates, maintenance of every once in a while, but really no big deal. iRedmail is a great system to get started with, I recently migrated off of that for something more lightweight but much of it was the same. Break free from monopoly email!

OpenBSD with smtpd, Dovecot, mariadb, spamd, httpd, roundcube and Baikal to replace all of what I used in iRedmail. I wanted to get it all to packages native or part of the pkg system for consistency. So far I've managed to migrate to a far less expensive VPS because performance requirements are lower but it's been a bit of a rocky transition while I'm learning the ins and outs. But it all works well when I'm telling it to do the right thing!

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