There probably are some very good reasons not to self host your email server but apparently my own, self hosted, email server's uptime over the last decade is now better than that of outlook.com :-D

Quick lets collect all options people have to self host! in addition to docker-mailserver im aware of

- https://github.com/stalwartlabs/stalwart

- https://github.com/mailcow/mailcow-dockerized

Mailcow's README is garbage. It tells me nothing about the software while asking for $50/m.

> Mailcow's README is garbage.

Geez, that's right! :-D

It seems to be a fairly popular project though, so what does that say about the correlation of README.md quality to success?

I decided to self-host my mail a few weeks ago and ran through all of the big names I'd heard - Mailcow, mailinabox, Stalwart, and Dovecot+Postfix; honestly I didn't like any of them. Stalwart is very corpo, hard to configure (reading the docs[0] confused the shit out of me[0]), and feels vibe-coded. Mailcow and miab push a huge stack onto you in a way that feels hard to modify yourself, e.g. expecting you to allocate ~2GB ram(?) to running ClamAV, and I never managed to get Dovecot+Postfix working properly.

In the end I paved over my Linux VM with OpenBSD and used Dovecot+OpenSMTPD which I found dead simple and so far faultless. I have nothing but kind words for it.

[0] https://stalw.art/docs/configuration/

That's fair. It is perfectly reasonable to want customizability if control is what you are after. I remember the days fondly where I was running postfix and dovecot on bare metal.

Nowadays my interests have skewed towards being able to have groupware features without much maintenance so groupware in a box suits my needs just fine. The learning curve to doing serious customization with a large FOSS groupware project might be a bit longer but that is offset by other factors.

Yeah I definitely get less done on OpenBSD, but I have more fun doing it, and fortunately in my position where that works for me. If I were providing a service to others instead of just myself I'd have to rethink my stack.

When your most important contacts use outlook, it does not matter what you do. Sending and receiving email when almost nobody else is sending and receiving is only small help.

Some problems are not solved by individual choice. If 30-40% of your important contacts use service is down, your ability to work goes down dramatically.

Enough of my contacts use Gmail. But both of these have more uptime than my self-hosted email.

Personal email is almost exclusively for OTP, reminders/invoice.

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>Learn all about and generate SPF, DKIM, and DMARC records but still regularly get sent to the spam folder or IP blacklists if your recipient has a big-provider email?

This is my biggest complaint when self hosting. You do everything right and they still send your mail to junk or just silently discard it while telling you 250-Ok for "reasons".

Microsoft have already recently kicked out self hosters from their "Smart Network Data Services" portal by only allowing the ASN owner (ie. your cloud provider) to access it.