Madd(eningl)y Simple Self Hosted eMail

Internet lore decrees that hosting your own email is impossible. Maybe not impossible but a disaster waiting to happen. Either its a Sisyphean task to configure and maintain, or you’ll never be able to send email to anyone.

Is it really? Someone has to host the email that you don’t want to.

I remember reading that 37Signals did their own email 10 years ago. If such a small company could do it, maybe it wasn’t that hard?

Having bought nye.lol for a federated social media instance (fediverse seems just as clunky to me). I decided what better domain to try hosting my own email. It’s a joke domain running joke services.

The traditional stack of postfix, dovecot et al. seemed a bit complicated. I’d recently passed by maddy.email and an all in one install initially appears to be more my style.

So, I went to digital ocean, span up their smallest instance and started down the install guide. Within an hour I had a working setup.

The question is, did it work?

Mostly. I drew a “clean” IP address from lottery that is getting IPs assigned from a cloud provider. MX Toolbox has a blocklist checker and it showed up just on the Barracuda and UCEPROTECT lists. UCEPROTECT is a pain because it uses blocks of IP addresses and also the organisation that owns them. However, my understanding is that UCEPROTECT isn’t well regarded as being a strong spam signal. Barracuda removed me from the list overnight after filling out a removal request.

My assumption has been that if you do the work to put in place all the right DNS records for email delivery. DKIM, DMARC, SPF, etc. Which are part of the tutorial for configuring Maddy - then you’ll be given the benefit of the doubt for sending email.

I’m yet to implement MTA-STS and DANE records, these are a little more involved. So far Gmail has worked flawlessly and Microsoft is an ongoing process. Microsoft seems to just block by default any IP that hasn’t been whitelisted. Unblocking was a simple process - but I still seem to be marked as spam.

So far, 2 days into hosting my email - things seem to be working well. The configuration was straight forward, documentation clear and conscise. Hosting hasn’t been a pain and I can mostly send emails from my joke domain. Time will tell if this turns into a Sisyphean task.

Postscript

After writing this I noticed that maddy does occasionaly crash. I’ve had it happen twice now in a week. Logging in and restarting service works. Fair warning - maddy is beta software.