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?
I have self hosted my email since 2006. I gave up on self hosting outgoing mail in 2021, but I still keep the server up for incoming mail, and still set up throwaway accounts on there.
The hard part of hosting email is getting Google and Microsoft to accept outgoing mail. Tons of businesses that do not have visibly “outlook.com” or “gmail.com” addresses are still hosted by those servers.
I had SPF, DKIM, and a static datacenter IP address with no reputation problems. I still couldn’t get through to Microsoft, not even in people’s junk mail directory, until they manually whitelisted my address. Microsoft didn’t allow them to whitelist a whole domain. Google was a little easier, but they added new demands monthly.
In 2025, I can’t get reliable delivery to gmail.com addresses even sending from a hotmail.com address in the outlook.com web interface.