I tried maybe 15 years ago and it went about as well as you’d expect for back then. But I’m starting to get the itch again.
Have any of you tried relatively recently? How impossible is it to get reliable deliverability to gmail and whatnot these days?
Reminder that you can go for hybrid approaches; receive email and host IMAP/webmail yourself, and send emails through someone like AWS. I am not saying you can’t do SMTP yourself, but if you want to just dip your toes, it’s an option.
You get many of the advantages; you control your email addresses, you store all of the email and control backups, etc.
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And another thing: you could also play with https://chatmail.at/relays ; which is pretty cool. I had read about Delta Chat, but decided to play with it recently and… it’s blown my mind.
Indeed. Owning your mail is a spectrum. I think it’s really best to transition from something like gmail to fully owning the stack in steps, over a significant amount of time. It will take a while to change over the address on everything a while anyway. No real need to go whole-hog right away and then burn out.