Self-Hosting Email Research Log

This rabbit hole started with trying to get off gmail, like any good rabbit hole, simple enough at first.

This will be a somewhat detailed report, for anyone also curious in this, with some musings on connections with ssb.

Notes:

• I installed yunohost on a digital ocean droplet, and used rainloop as an email client. Pretty cool how easy it is to install apps with it, install letsencrypt certificates for domains, pair domains with apps, and that it comes with a full email stack included by default including postfix and all the correct dkim and spif settings which I don't fully understand

• However, even with all the correct settings, when I started sending emails... many were ending up in people's spam folders because they were coming from an "unknown IP address" (according to gmail, yahoo etc.)... when I realized this, it seemed like a sort of failed experiment. The path to becoming a "known IP address" sounded long and fraught

• based on the recommendation of a blog post of someone who has been self-hosting email for 14 years I ended up configuring it so my outgoing email goes through an smtp relay provided by dreamhost (which is the domain registrar I used). this somewhat defeats the purpose of self-hosting, as my email now still goes through dreamhost, a service which I pay for, but it means I'm able to reliably send and receive emails (I think)

• with this setup, my email does seem to be quick to load and I like the rainloop UI. I also like that I could easily port this setup to a local server at somepoint, and it should theoretically still work (since I'm using an SMTP relay to send anyway).

image of the rainloop UI, you can also see it at their demo app

Learnings / thoughts:

• setting it up was complicated enough, and annoying that I have to use the relay, that I wouldn't really recommend this to anyone, especially non-technical friends. Most of my interest in self/community-hosting is in thinking about how things could be extended to serve not just technical folks, so this setup is not great in that regard

• I now understand the dark side of email and spam filtering. interesting how gmail spam filtering has effected the decentralized email space, by making the spam filtering somewhat centralized in nature.
  this makes me excited about ssb private messages... its so direct... P2P... it feels really good in comparison. it also makes me wonder, what will attempts by spammers look like on ssb if it ever gets that popular so they really come out?

• related to above, in an ideal world, I would like to be able to provide an ssb address on a website such that someone I've never met before could get in touch with me... but also not to be overrun with spammers... maybe its not possible to have both... but maybe there is some way?

• given how complicated it was to setup, I'm also still dreaming of collectives that host your services for you, but using all open source software. You pay for the service, but they use open source tools and give you a sort of whole package. Not just another email company. More like a small collective that host multiple open source services for you and make sure its well operated and secure, ideally also using E2E tools (like ssb private messages) where they don't have access to your personal data either.

#email #community-infra #yunohost #self-hosting #rainloop

@cblgh omg the writing on the migadu pros/cons page is a fresh of breath air compared to other BigCo copywriting. also some interesting commentary there on blacklists and spam

Running a blacklist is not even close to the task of running an email service. To add to the insult, some blacklist require a removal fee, making them really - blackmailers.

We refuse to use blacklists and encourage others to consider dropping the same.

The micro service at 20 dollars per year seems like a very solid option.

Makes me also wonder if someone somewhere could even offer a micro-micro option for usage by a self-hosted setup like mine, which was just the SMTP relay, with no storage, but with strong guarantees of privacy and zero logs. I'm also now curious if I can use disroot as an smtp relay, possibly for free, instead of dreamhost, but haven't looked into it yet.

following up on this, I am overly-excited with the system I came up with.

My original yunohost setup was working, but I became paranoid that at some unfortuitous moment my server would go down, and I would not receive an important email... or nightmares of travelling and my server is down and I don't have a computer or the ability to fix it...

I decided to follow the suggestion of benou — to create a webmail account with the exact same email addresses, and then to setup three MX records. The first MX record points to my yunohost server with priority 10, the second MX records points to my webmail server with priority 20, and the third MX record points to my webmail's backup server with priority 30 — I was excited to see that this does work as expected... if I turned off my yunohost server, and sent myself an email from elsewhere... it would indeed arrive at my webmail/"backup receiver"... I can sleep easy knowing that there is a backup receiver if my server ever goes down, and if I'm travelling and really don't have time to deal with anything, I could always just remove the first MX record, and use the webmail normally

I then configured a cron job which runs fetchmail every 15 minutes, to fetch any emails from the webmail and bring them into yunohost, in case some email accidentally got delivered to the backup receiver

In the future, if I had a close friend who also had a yunohost or a hosting collective I was a part of, I could imagine to use this system with my friend's server as the backup receiver, instead of the webmail as the backup receiver -- I think a key part of the relief of the backup, is that its another person, and something I can fallback on, if I don't feel able (something to think about in the sometimes-individualistic paradigm of self-hosting...)

of course this is all somewhat unnecessary, and just using Migadu webmail normally seems like a good option too, but this was for some reason interesting to me, and I'm happy with what I learned from it. here is a more detailed tutorial on my setup in case any future readers want to replicate it