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Self-hosting email in 2025 is easy actually (apart from M365)

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21–30 of 79 posts

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#21
Actual situation:

Self-hosting email is great, if you have plenty of free time to waste, and if you don't particularly care if your messages are delivered.

One little thing the OP failed to mention is that even if you get a "lucky IP address" today, it can be randomly blocked (with no recourse) tomorrow by Google.

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#22

> 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 u…

>> 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.

This does not follow.

There can be delivery problems between Gmail and m365 - and even between m365 and m365 - and vice-versa.

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#23
post #4

Earlier quoted context omitted.

The whole IP reputation problem seems to mostly be a Google/Microsoft problem. Unfortunately, most of the world seems to use one of those two platforms. Routing mail to those two services via a third party seems like the wisest choice. May I ask how you implemented that?

I use exim4. So after doing the usual SES setup, I can change the smarthost router to look like this: SMARTHOST_FOR_MS = email-smtp.us-east-2.amazonaws.com::587 smarthost: debug_print = "R: smarthost for $local_part@$domain" driver = manualroute domains = ! +local_domains transport = remote_smtp_smarthost route_list = hotmail.com SMARTHOST_FOR_MS byname ; \ live.com SMARTHOST_FOR_MS byname ; \ outlook.com SMARTHOST_F…

How about custom domains hosted on m365?

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#24

I used to host my own email until switching to Fastmail. I recall roundcube to be pretty much the best webmail offering back when I was hosting but also severely lacking two important features: 1. Fast search against mailbox folders/labels with say 100k+ messages. 2. Handling multiple aliases, both individual and catch-all, and being able to automatically respond with the correct alias if an email is received using o…

But the real reason I stopped running my own mail is that I didn't trust myself with regular backups (even though I still do them via IMAP on occasion) and disaster recovery. I don't think anyone self-hosting really has this figured out.

On the server itself a cronjob calling rsnapshot [1] is a good habit in the event something gets corrupted or someone deletes mail by mistake and you want to save the day. RSnapshot uses hardlinks to avoid copying the same data to keep the size small which allows for many snapshots. Then a cronjob to call a script that uses either lftp+sftp+mirror or rsync to back up all the important things to a standby node along with a corresponding script on the standby node to quickly copy everything into place and start everything in an idempotent manor can get one back into operation quickly. All of this should be tested quarterly in the event some software update breaks any assumptions.

If running this on VM's in a VPS provider there may be an option in the VPS control panel to swap IP addresses on the active and standby assuming they are in the same region.

[1] - https://rsnapshot.org/rsnapshot/docs/docbook/rest.html

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#25
post #18

My experience says quite the contrary: nowadays you have to be a mail giant to be able to send more than one mail. I.e. policy imposed by Gmail and M365 will keep you at bay from delivering the mail in more copies (e.g. to your subscribers), marking you as a potential spammer.

> will keep you at bay from delivering the mail in more copies (e.g. to your subscribers)

Well, sad fact is that one person's exiting subscription email is another person's spam.

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#27
post #6

Earlier quoted context omitted.

You can usually switch host. Some have better IP reputations than others. There are quite a few other providers of email forwarding services, although I might look at SES myself if its that cheap as I have issues with hotmail (I seem to be OK with most mail to email on MS hosted email on other domains, oddly enough).

> You can usually switch host ...it took OP 8 months of "rolling the gacha" and waiting to get a clean IP; no mention of costs. Not really a solution in my book. If you're willing to wait 8 months for working email, I put it to you you're actually using some other provider for your life and the thing you are playing with is a toy. I've been self-hosting my email for a pretty long time. I first started down the reputa…

If cost is not an issue one can run standby servers in multiple locations and have backups to all of them. Just as MX records allow for multiple inbound servers one can have multiple outbound servers as well. Park a few unused or vanity domains on them and have cronjobs send automated emails to yourself. I reply to those emails so the likes of Gmail see interaction between them. With time all IP addresses get good reputation.

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#28

I've been running my own mail server with several domains for me, my now wife, and friends since 1999. It's definitely changed with time and gotten more strict with things like spf, dkim, dmarc, and reverse dns all becoming necessary over the years. But it's not that difficult to be honest. Currently my internet provider is init7 and they offer fixed ip4 and set the reverse dns for me which lets me run the server dow…

I’m surprised this works, usually residential IP blocks are in DNSBL.

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#29
post #22

> 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 u…

>> 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. This does not follow. There can be delivery problems between Gmail and m365 - and even between m365 and m365 - and vice-versa.

> 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.

Re: Self-hosting email in 2025 is easy actually (apart from M365)

#30
post #22

> 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 u…

>> 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. This does not follow. There can be delivery problems between Gmail and m365 - and even between m365 and m365 - and vice-versa.

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.
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