I self-hosted for well over 20 years, I did not throw the towel and I do not plan to. Self-hosting is a sign of pride. Neither my government nor my Prime Minister nor even my Ministry of Interior or Foreign Ministry can host their own email.
Last time I checked, only State Security self-hosted.
I was probably lucky, but I rarely had delivery problems. The last one was a couple years ago with Microsoft swallowing my emails and it was due to the combination of a fairly old exim and a TLS certificate verification quirk at *.protection.outlook.com. I found a fix in the form of a configuration option somewhere on SO.
In all fairness, there is very little maintenance involved, and whenever I have to do maintenance work, I take the opportunity to learn something new. Like this year, I decided to finally replace my aging Debian jessie setup by Arch Linux, and I rewrote all cron jobs as systemd timers.
I must admit that when I send a really important email, I check the mail server log if it went off without errors, but this does not bother me as checking logs manually once in a while is a good thing anyway.
Lastly, a piece of advice: treat self-hosting like a hobby and learn to enjoy it.
Oh and the very last thing: the person who designed Exim configuration for Debian deserves a special place in hell for all the hours wasted. If you set up Exim on Debian, just figure out how to use the upstream exim config and adapt it to your needs.
The Canadian government too. They let Microsoft do it. A company headquartered in a country threatening to annex Canada, and known to collaborate with their spy agencies.
From what I know, it's worse. They are afraid of IT departments owning their infrastructure. They'd rather have a US-based megacorp handle IT because it shield politicians from craftsmen and their realisation of power.
There was a blog posted to HN years ago describing a self hosted email setup in detail, and this was indeed the main issue. Everyone he emails is on a small number of big companies, and most of them don't like his server.
Edit:
"After self-hosting my email for twenty-three years I have thrown in the towel"
One problem in this are bad actors. German Telecom for example (t-online.de) only accepts mails from servers it whitelists.
To get whitelisted you have to apply with them and your domain HAS to have a website with an Impressum, your clear legal name AND an email that is NOT your domain for emergency contact. It is insane. If every provider would act like that, email would die in a month.
> The elephant in the room is real-world deliverability. With self-hosting you risk not receiving mail or someone missing your mail. I accept this for my personal projects, but you may not. Keep this in mind.
Not self-hosting if you actually need email does not address the elephant that self-hosting email doesn't actually do email. I say this as someone who self-hosted for several years but had to give up because important emails were discarded. Until the deliverability issue is actually addressed, self-hosting is not viable for email.
I’ve been self hosting my email for thirty years. I don’t have any more deliverability issues than I do at work using a major provider. It is entirely viable.
I went back to self hosting when Google were going to kill free Gmail for your domain. I have no problems with deliberability. And I have tiny mail volumes.
Pre Gmail I was on Exim. Now I'm on Postfix. I used the 123qwe.com tutorial as a starting point.
The real problems are (1) family members just want Gmail and (2) I have to maintain an email system.
My first email usage was at University, pre-WWW. After that I briefly used some ISP email service, but that was on a time of very limited storage and POP only accounts, so I started hosting my own email even before having an always-on internet connection, using a relay and dynamic DNS to receive email when online.
Now a days, I use a small VPS to route and receive email, but final destination and storage is on my home server.
Over the years, I had, like others here, to ask Outlook and other providers to unblock my IP or domain, but it has been rare.
I really don’t want to live in a world where only two or three companies run email for the entire world, and this is my little act of resistance.
I do wonder about reliability. The only things I'm missing are the PTR record and reputation from what I gathered. Even if the mail server goes down, mail gets to me because email providers attempt to deliver again.
Anyway, I added a disclaimer at the top, so people don't treat this as a production ready setup.
DMARC is for setting policy to authenticate email which ends up becoming a requirement to even send mail to other providers, amongst an evolving set of policies which may cause your emails to be silently undelivered.
