> i think the myth of "you can't self-host email" persists because while it can evidently be done, basically all of the software involved is ancient, baroque, inconsistently documented, requires a PhD in Bullshit to correctly configure, and is almost actively hostile to observation. but this is _annoying_, very different from _impossible_, and fortunately mostly solvable by delegating the annoying bits to an expert using something like NixOS to make it reliably work
Why are they calling this a “myth” when they readily admit that even when you are an expert who has been doing it for years, there’s still problems sending to the biggest providers in the world?
There is zero practical difference between “you need to be an expert and you will still fail to get something fundamental working” and “you can’t self-host email”.
> Microsoft 365 however apparently will hate your email no matter what. you learn to live with it
Or you don’t self-host but use a major email provider and don’t have the problem.
> there exist several pieces of folk wisdom:
> - "you cannot run your own mail server in 2025, this is too hard and time consuming" (completely false, i've done this since ~2010 with minimal ongoing maintenance)
This seems completely true according to what they themselves write. It is too hard and time consuming.
> I think the combo of "roll the IP gacha a few times" + "let it sit for 8 months while the VM idles" probably did me a lot of good here
Is letting it sit for eight months not “time consuming”?
> until I cleaned up my IP reputation (which has been awful for almost a decade) Gmail refused to deliver to anything but spam
This is not in any way acceptable to the average person, and it does not meet what most people would describe as “I can self-host email”. “I can self-host email but Gmail sends me to spam” is functionally equivalent to “I cannot self-host email”.
I self-host my mail server since at least 2001 and while it occasionally requires hours of intense work, I consider it a hobby and a way to refresh Linux System Administration skills.
> There can be delivery problems between Gmail and m365 - and even ... - and vice-versa.
Absolutely not on the same scale as 'your' mail-in-a-box toy, though. I'm with OP, even for those who can roll Exim with NixOS or whatever the latest fashion is: mail is not worth the hassle.
I pay Zoho and do/host better things with my time [nearly anything], I have nothing to prove. They [or another provider, not an ad] can fight the mail hegemony; not interested, personally.
There is a difference though between “it will not work no matter what” with self hosting and “there is chance it will not work” with a hosted solution.
Mine does. I would prefer if it doesn't as that means that I can't reject SPAM that wouldn't pass address verification, but using it for sending is nice.
Microsoft 365 is corporate business email for corporate businesses. If you're a corporate business, you're already using it, and if you're not then you probably don't want to talk to anyone who's using it anyway. Even if you could pass their filtering, they'd just manually ignore your emails because they only want to talk to corporate businesses.
Maybe persons and families should stop using email services that refuse to deliver them the emails they want. If I personally use /dev/null as my inbox does it become your problem to ensure mail delivery?
I recommend that whenever you know someone cares about receiving an email much more than you care about them receiving it, just send it. They'll do what they have to, and this way we can weed bad providers out of the market. Some websites with email verified sign-up have a simple FAQ to let you know what's causing the problem.
Most people at e.g. Oxford and Cambridge (and, I suspect, many other universities) use their university emails for a fairly wide variety of extramural correspondence, and are stuck with M$ as the provider, alas.
Why are they calling this a “myth” when they readily admit that even when you are an expert who has been doing it for years, there’s still problems sending to the biggest providers in the world?
There is zero practical difference between “you need to be an expert and you will still fail to get something fundamental working” and “you can’t self-host email”.
> Microsoft 365 however apparently will hate your email no matter what. you learn to live with it
Or you don’t self-host but use a major email provider and don’t have the problem.
> there exist several pieces of folk wisdom:
> - "you cannot run your own mail server in 2025, this is too hard and time consuming" (completely false, i've done this since ~2010 with minimal ongoing maintenance)
This seems completely true according to what they themselves write. It is too hard and time consuming.
> I think the combo of "roll the IP gacha a few times" + "let it sit for 8 months while the VM idles" probably did me a lot of good here
Is letting it sit for eight months not “time consuming”?
> until I cleaned up my IP reputation (which has been awful for almost a decade) Gmail refused to deliver to anything but spam
This is not in any way acceptable to the average person, and it does not meet what most people would describe as “I can self-host email”. “I can self-host email but Gmail sends me to spam” is functionally equivalent to “I cannot self-host email”.