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I just recently started self hosting email. I settled on relaying through gmail to all hosts except a whitelist of hosts I know won't blackhole me - mostly just

I just recently started self hosting email. I settled on relaying through gmail to all hosts except a whitelist of hosts I know won't blackhole me - mostly just a few niche domains of friends who do the same thing or small organizations they're a part of. Have you considered this? It's not optimal but it's a practical compromise. You get to keep your From: field as your domain too if you set it up right. I couldn't make it into Microsoft inboxes at all before I set up the relay but now I can. - Make a gmail account just for your email server, which forwards anything incoming to your host in case someone emails it directly (you'll be able to discover this gmail address if you dig through delivered emails' headers but it won't be in the From: field) - Let Gmail authenticate with your SMTP server in Gmail's advanced options, and make sure the options are checked to retain the From: headers of relayed emails - Generate an App Password and set up your mail server software to use Google's SMTP relay with the email and app password There are other services to do this too I'm sure, but I'm happy with Gmail for now. And you can always transparently switch it out to another service if Google pulls something. I plan to write a blog post on the whole process of setting up a mail server to configuring it with a gmail relay like this.

thaumaturgy 4y ago
I did consider that as an option, and I tried routing email through a number of other delivery services, but ultimately I rejected it for a few reasons: I was hosting email not just for myself but for a few other people, and that gets tricky to route through Gmail; Gmail could change their policies at any time and give me a really bad day, potentially when I can't respond to it in a timely manner; If routing email in this way ever triggers Google's abuse mechanisms, then potentially I'm losing access to a lot of the Google network, and while I don't use it for anything personally, sometimes I have to work with companies that do; After spending tons of hours dealing with Gmail-related headaches despite not using Gmail myself, relying on them to get mail routed felt like a deal with the devil. I've instead helped a bunch of people get set up with Fastmail. I love Fastmail, they're great, I miss hosting my own email but they're the next best thing. Fastmail must be handling enough traffic that they're hovering above Gmail's piss-off threshold, and really my experience with them has been extraordinarily good. Everyone I've set up over there has been happy with them too, save for one person who got told by the next IT hat-wearer that "everyone's using Google Workspace and you should be too" (and then immediately ran into a problem during setup that snowballed into a big hairy mess).
- GoblinSlayer 4y ago
  >felt like a deal with the devil Why not if you send mail to hell? Who else do you expect to deal with?

thaumaturgy 4y ago

I did consider that as an option, and I tried routing email through a number of other delivery services, but ultimately I rejected it for a few reasons: I was hosting email not just for myself but for a few other people, and that gets tricky to route through Gmail; Gmail could change their policies at any time and give me a really bad day, potentially when I can't respond to it in a timely manner; If routing email in this way ever triggers Google's abuse mechanisms, then potentially I'm losing access to a lot of the Google network, and while I don't use it for anything personally, sometimes I have to work with companies that do; After spending tons of hours dealing with Gmail-related headaches despite not using Gmail myself, relying on them to get mail routed felt like a deal with the devil. I've instead helped a bunch of people get set up with Fastmail. I love Fastmail, they're great, I miss hosting my own email but they're the next best thing. Fastmail must be handling enough traffic that they're hovering above Gmail's piss-off threshold, and really my experience with them has been extraordinarily good. Everyone I've set up over there has been happy with them too, save for one person who got told by the next IT hat-wearer that "everyone's using Google Workspace and you should be too" (and then immediately ran into a problem during setup that snowballed into a big hairy mess).

GoblinSlayer 4y ago
>felt like a deal with the devil Why not if you send mail to hell? Who else do you expect to deal with?