Self-Hosted Email With maddy: A Naive First Attempt

How hard could it be?

This post is part of a series:
Previously: Goodbye, Github Pages
Next: Setting Up maddy On A VPS

For a long time now I’ve wanted to get off gmail and host my own email domains. I’ve looked into it a few times, but have been discouraged on multiple fronts:

  • Understanding the protocols underlying email isn’t straightforward; it’s an old system, there’s a lot of cruft, lots of auxiliary protocols that are now essentially required, and a lot of different services required to tape it all together.

  • The services which are required are themselves old, and use operational patterns that maybe used to make sense but are now pretty freaking cumbersome. For example, postfix requires something like 3 different system accounts.

  • Deviating from the non-standard route and using something like Mail-in-a-box involves running docker, which I’m trying to avoid.

So up till now I had let the idea sit, waiting for something better to come along.

maddy is, I think, something better. According to the homepage “[maddy] replaces Postfix, Dovecot, OpenDKIM, OpenSPF, OpenDMARC and more with one daemon with uniform configuration and minimal maintenance cost.” Sounds perfect! The homepage is clean and to the point, it’s written in go, and the docs appear to be reasonably well written. And, to top it all off, it’s already been added to nixpkgs!

So in this post (and subsequent posts) I’ll be documenting my journey into getting a maddy server running to see how well it works out.

Just Do It

I’m almost 100% sure this won’t work, but to start with I’m going to simply get maddy up and running on my home media server as per the tutorial on its site, and go from there.

First there’s some global system configuration I need to perform. Ideally maddy could be completely packaged up and not pollute the rest of the system at all, and if I was using NixOS I think that would be possible, but as it is I need to create a user for maddy and ensure it’s able to read the TLS certificates that I manage via LetsEncrypt.

sudo useradd -mrU -s /sbin/nologin -d /var/lib/maddy -c "maddy mail server" maddy
sudo setfacl -R -m u:maddy:rX /etc/letsencrypt/{live,archive}

The next step is to set up the nix build of the systemd service file. This is a strategy I’ve been using recently to nix-ify my services without needing to deal with nix profiles. The idea is to encode the nix store path to everything directly into the systemd service file, and install that file normally. In this case this looks something like:

pkgs.writeTextFile {
    name = "mediocregopher-maddy-service";
    text = ''
        Description=mediocregopher maddy



        # cd to state directory to make sure any relative paths
        # in config will be relative to it unless handled specially.

        # ... lots of directives from
        # that we'll elide here ...

        ExecStart=${pkgs.maddy}/bin/maddy -config ${./maddy.conf}

        ExecReload=/bin/kill -USR1 $MAINPID
        ExecReload=/bin/kill -USR2 $MAINPID


With the service now testable, it falls on me to actually go through the setup steps described in the tutorial.

Following The Tutorial

The first step in the tutorial is setting up of domain names, which I first perform in cloudflare (where my DNS is hosted) and then reflect into the conf file. Then I point the tls file configuration line at my LetsEncrypt directory by changing the line to:

tls file /etc/letsencrypt/live/$(hostname)/fullchain.pem /etc/letsencrypt/live/$(hostname)/privkey.pem

maddy can access these files thanks to the setfacl command I performed earlier.

At this point the server should be effectively configured. However, starting it via systemd results in this error:

failed to load /etc/letsencrypt/live/ and /etc/letsencrypt/live/

(For my own security I’m not going to be using the actual email domain in this post, I’ll use instead.)

This makes sense… I use a wildcard domain with LetsEncrypt, so certs for the mx sub-domain specifically won’t exist. I need to figure out how to tell maddy to use the wildcard, or actually create a separate certificate for the mx sub-domain. I’d rather the former, obviously, as it’s far less work.

Luckily, making it use the wildcard isn’t too hard, all that is needed is to change the tls file line to:

tls file /etc/letsencrypt/live/$(primary_domain)/fullchain.pem /etc/letsencrypt/live/$(primary_domain)/privkey.pem

This works because my primary_domain domain is set to the top-level (, which is what the wildcard cert is issued for.

At this point maddy is up and running, but there’s still a slight problem. maddy appears to be placing all of its state files in /var/lib/maddy, even though I’d like to place them in /mnt/vol1/maddy. I had set the WorkingDirectory in the systemd service file to this, but apparently that’s not enough. After digging through the codebase I discover an undocumented directive which can be added to the conf file:

state_dir /mnt/vol1/maddy

Kind of annoying, but at least it works.

The next step is to fiddle with DNS records some more. I add the SPF, DMARC and DKIM records to cloudflare as described by the tutorial (what do these do? I have no fuckin clue).

I also need to set up MTA-STS (again, not really knowing what that is). The tutorial says I need to make a file with certain contents available at the URL I love it when protocol has to give up and resort to another one in order to keep itself afloat, it really inspires confidence.

Anyway, I set that subdomain up in cloudflare, and add the following to my nginx configuration:

server {
    listen      80;
    include     include/public_whitelist.conf;

    location / {
        return 404;

    location /.well-known/mta-sts.txt {

        # Check out openresty if you want to get super useful nginx plugins, like
        # the echo module, out-of-the-box.
        echo 'mode: enforce';
        echo 'max_age: 604800';
        echo 'mx:';

(Note: my public_whitelist.conf only allows cloudflare IPs to access this sub-domain, which is something I do for all sub-domains which I can put through cloudflare.)

Finally, I need to create some actual credentials in maddy with which to send my email. I do this via the maddyctl command-line utility:

> sudo maddyctl --config maddy.conf creds create '[email protected]'
Enter password for new user:
> sudo maddyctl --config maddy.conf imap-acct create '[email protected]'

Send It!

At this point I’m ready to actually test the email sending. I’m going to use S-nail to do so, and after reading through the docs there I put the following in my ~/.mailrc:

set v15-compat
set mta=smtp://[email protected]:587 smtp-use-starttls

And attempt the following mailx command to send an email from my new mail server:

> echo 'Hello! This is a cool email' | mailx -s 'Subject' -r 'Me <[email protected]>' '[email protected]'
reproducible_build: TLS certificate does not match: localhost:587
/home/mediocregopher/dead.letter 10/313
reproducible_build: ... message not sent

Damn. TLS is failing because I’m connecting over localhost, but maddy is serving the TLS certs for Since I haven’t gone through the steps of exposing maddy publicly yet (which would require port forwarding in my router, as well as opening a port in iptables) I can’t properly test this with TLS not being required. It’s very important that I remember to re-require TLS before putting anything public.

In the meantime I remove the smtp-use-starttls entry from my ~/.mailrc, and retry the mailx command. This time I get a different error:

reproducible_build: SMTP server: 523 5.7.10 TLS is required

It turns out there’s a further configuration directive I need to add, this time in maddy.conf. Within my submission configuration block I add the following line:

insecure_auth true

This allows plaintext auth over non-TLS connections. Kind of sketchy, but again I’ll undo this before putting anything public.

Finally, I try the mailx command one more time, and it successfully returns!

Unfortunately, no email is ever received in my gmail :( I check the maddy logs and see what I feared most all along:

Jun 29 08:44:58 maddy[127396]: remote: cannot use MX        {"domain":"","io_op":"dial","msg_id":"5c23d76a-60db30e7","reason":"dial tcp connect: connection timed out","remote_addr":"142.250.152.
26:25","remote_server":"","smtp_code":450,"smtp_enchcode":"4.4.2","smtp_msg":"Network I/O error"}

My ISP is blocking outbound connections on port 25. This is classic email bullshit; ISPs essentially can’t allow outbound SMTP connections, as email is so easily abusable it would drastically increase the amount of spam being sent from their networks.

Lessons Learned

The next attempt will involve an external VPS which allows SMTP, and a lot more interesting configuration. But for now I’m forced to turn off maddy and let this dream sit for a little while longer.

If you liked this post, consider checking out other posts in the series:
Previously: Goodbye, Github Pages
Next: Setting Up maddy On A VPS