I have compiled my official mail provider recommendations. With any provider, you must always use your own domain.
Good: Down to earth. Unlimited domains, storage, etc. Full marks for philosophical, ethical, and technical merits.
Bad: Difficult to set up. UI is a bit confusing. Advertises itself in your signature in the free plan. Apparently blocks VPN and Tor users (I have reached out to them about this).
Note: Was unable to evaluate their webmail
Good: excellent PGP support and good on other security fronts as well
Bad: requires google captcha, does not handle plaintext as well as I'd like, german leaks through into the english interface sometimes, too scatterbrained
Good: Goes above and beyond in support for various standards and protocols, handles plaintext email very well. Lots of good options for account security.
Bad: rough UI
migadu is hard to set up but is the best all-around offering. If you're security concious, mailbox.org has the best PGP support and good all-around security; runbox.com has good account security options but no built-in PGP support.
Evaluated but not recommended: disroot, fastmail, posteo.de, poste.io, protonmail, tutanota, riseup, cock.li, teknik, megacorp mail (gmail, outlook, etc)
For your own mail server, I recommend setting up a box with Alpine Linux, postfix, dovecot, and opendkim to sign outgoing email, with no webmail. I also recommend running your own DNS server with bind9. Test your mail configuration with mail-tester.com.
I do not endorse any fast-and-easy docker-based solutions.
@sir I would add here that a big challenge is getting an IP with a clean bill of health from whichever hosting provider this server ends up on.
And that it may also mean not being able to reliably send email to megacorps for at least a year (or in case of outlook.com forever because they're that obnoxious) no matter how perfect your setup is with all the bells and whistles.
Whether that is a dealbreaker or an advantage is very subjective :)
Maybe not difficult, but tedious. Microsoft for example is known to block whole /24 subnets for spam. If anyone on your network subnet is using the IP for spam, its pretty easy to get caught on the backwash and you need to deal with a lot of unsupportive staff to get of their blacklist. These kind of unwritten rules by the big three made me stop hosting my own mail in the end.
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