Thanks for this thread, I have exactly the same use-case, but I have not yet had the time to actually research too deep into it so I am unfortunately still relying on Google.

My partial conclusions:
- I’ve been using the AnonAddy approach for 20 years now with my own domain, like many others have. You do not actually need a full suite for this, just setup your incoming email on your domain with a wildcard, choose a unique email address for everything you sign up for, and that is it. Sidenote: You’ll be amazed at the confused faces you get when “Joe Plumbing Co” requests your email address and you reply "joeplumbing@yourdomain.com".
- For outgoing mail, just use SMTP2GO on the free tier, it works fine and I’ve never had delivery problems. Ignore everyone that talks about IP reputation making it impossible to self-host, while it is true, there are several suppliers with a free tier or a very low cost that take care of this for you. I use it nowadays with Thunderbird because for some reason I was unable to properly use custom aliases with the Google SMTP server.
- For incoming mail, you will probably need a better plan than self-hosting. Your server needs to be up 24/7 or you will end up losing email, so it is probably better to have a cloud-based incoming server that holds it and forwards to your server when it actually becomes available. I’m still investigating this part but it would seem that Cloudflare Mail Routing should work.

I have not yet found what the best solution is to the self-hosted archival search problem, please share your findings!

The general consensus is that its not worth the headache to selfhost email.

Have a look at mailcow if you’re new to MTA’s. Use that and a (sub)domain to figure out how to set things up. Once youre satisfied with the setup, reconfigure your domain on the new MTA. Use a mailclient with $yourformat and imap support to import your old email.

And above all, dont be discouraged by the naysayers that think its an impossible task; Its not, but it is complicated to get right bc all the parts involved ;-)

If you’re going to selfhost anonaddy (or simplelogin, since both are rather similar) then you wouldn’t need to selfhost a full blown mailserver anymore.

You pick either one, not both. Anonaddy and simplelogin will act as a relay and would forward the mails to somewhere else, usually the mainstream hosted providers gmail, yahoo, proton, tuta etc and those providers will be the one that actually stored the final mail. Relaying to a full blown mailserver hosted yourself would totally negate the point of both anonaddy and simplelogin.

Most full blown mailserver also can act as anonaddy/simplelogin with their built-in alias manager so it’ll just overlap.

I used Luke Smith’s emailwiz script.

Postfix, dovecot and everything. Works wonders.

https://github.com/LukeSmithxyz/emailwiz

Edit: I am unsure if you can import into dovecot as I never had to, but I think the documentation would be useful.

Advice: don’t

I’ve used iRedMail hosted at home for the last year or so and love it. Even has ActiveSync integration for mobile devices. The key to selfhosting email IMO is to use a SMTP relay service to send outbound mail. I use SMTP2Go and it just works, even free. Everyone’s complaints about blacklists and reputation go away when you use a reliable relay.

the biggest problem with hosting email is that the main way of contacting everyone you need to contact when someone (your provider, client, client’s network admin, partner, vendor, customer, etc) has broken your email service is also email.

I don’t trust anyone to host my email for me, esp. cloud service providers where your data could be ANY…WHERE in the World. I trust ‘me, myself, and I’ sandwiched behind 3-4 firewalls.

I’m also using ‘ciphermail’ for sending/receiving encrypted emails, too for the more ‘sensitive’ material (nothing illegal; just proprietary projects and don’t want Google sniffing around).

It also helps that I ‘own’ (and I use that term very loosely) my IP addresses, so it kinda helps with reliability and veracity issues.

Personally I think poste.io is a great solution. It’s fairly lightweight, easy to set up and has a great interface. I am surprised it’s not mentioned more often.

I use Proxmox Mail Gateway (as a mail gateway) and I can only recommend that. It keeps spam at nearly zero and it is very lightweight and easy to set up. Plus it gives you flexibility where and how to host the actual mail server.

Microsoft has blacklisted most IPs so you’ll most probably need to send them a message to whitelist your mail server or gateway once everything is configured correctly.

If you’re looking for a more than just plain mail check out solutions like Grommunio and Axigen. Some commercial solutions have free versions with minor limitations.

Importing old emails can be done via the client and not directly at the server. There are good solutions for mail archiving and searching (like Mailstore). I’d use that for mails older than two years.

While I like to idea of AnonAddy and I understand your reasons, I just don’t think it is worth the hassle. Eventually your “real” email address will somehow end up in spammers list, but a good spam filter, like the one in Proxmox mail gateway will keep your mailbox clean.

All in all, self hosting a mail server is a bit of work in the beginning, but definitely doable.

I’ve recently started selfhosting email using docker mail server and honestly it’s quite straightforward. I have it on my server at home, all outgoing mail leaves using my home it (and honestly I’m quite impressed because I am behind CGNAT) and incoming mail goes (as the rest of my incoming traffic) through oracle vps via Haproxy (with proxy protocol)

This might sound complicated but honestly I had vps setup earlier so the “extra work” I had to put in was adding few ports to haproxy config using my existing config as a template (had to add like 2 ports)

I’ve self-hosted my email for over 25 years now and just finished migrating my ancient Postfix+Exchange setup to Mail-in-a-Box. I couldn’t be happier with how well it worked, all things considered. I used good old ExMerge to dump mailboxes to PST files, and then I used Outlook plus CalDav Synchronizer to import everything. The only things that didn’t transfer cleanly were calendars, but the important calendar items for things like birthdays were all recreated when I transferred the contacts over.

You certainly can do this, but email is one of the few things I recommend not self hosting. My experience working at a spam filtering company really taught me how bad this can be.

Here’s some of the reasons why I recommend against it:

Not getting an important email delivered because it came from a residential IP range and that alone puts you on several anti spam lists.

Not receiving an important email because some email admins put the blocklists on in both directions.

Sudden email issues because your IP changed. And now you have to re apply for all the blacklist removals again.

Internet/power goes offline at home, and some senders aren’t configured to retry.

Get hit with a joe job attack and get gigabytes per hour of spam permanently, with no real way to stop it.

You may be sending and receiving too little email to actually remain in the good behavior cache for many spam filters.

One overeager cronjob or broken script and now you are on even more blacklists.

Misconfigure your server slightly and you are now a spam relay. Spammers scan the internet regularly for targets. You are not small enough to escape notice.

In case of house fire, what is your recovery plan? Have you tested it? Can you send “I’m okay” or insurance docs around if this system is permanently offline? How many weeks do you end up with zero email? How about people who depend on you as their provider?

Don’t.