Self-hosting email in 2025 is easy actually (apart from M365)
1–10 of 79 posts
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#2IP reputation is a gamble, and there is no recourse. If you're lucky, awesome. But if you're unlucky and switching host isn't an option, you pretty much have to involve a large third party to act your behalf - there is zero appetite in the industry for interacting with individuals.
The best solution I've been able to find is to self-host /almost/ everything, but route outgoing mail through Amazon SES.
The pricing for vanity email volumes is negligible (a few cents a year), and they have people whose full time job is wrangling IP reputation / Office 365 / etc.
This setup has survived several ISP/hosting switches; at times when I am lucky with IP reputation I route only mail going to Office 365 recipients via SES and deliver the rest directly; at times when I am less lucky, everything goes via SES.
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#3O365 and gmail should be honorably mentioned as places that will deliver both inbound and outbound to/from an IPv6-only MX.
A lot other servers will not play ball here. Your self-hosted mail server, if it lacks IPv4, will not get inbound from mailgun, mailjet, github; neither will it be able to send outbound to cisco/iphmx, as well as about 90% of small servers from what I see in my logs.
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#4IP reputation is a gamble, and there is no recourse. If you're lucky, awesome. But if you're unlucky and switching host isn't an option, you pretty much have to involve a large third party to act your behalf - there is zero appetite in the industry for interacting with individuals. The best solution I've been able to find is to self-host /almost/ everything, but route outgoing mail through Amazon SES. The pricing for…
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?
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#5> 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”.
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#6IP reputation is a gamble, and there is no recourse. If you're lucky, awesome. But if you're unlucky and switching host isn't an option, you pretty much have to involve a large third party to act your behalf - there is zero appetite in the industry for interacting with individuals. The best solution I've been able to find is to self-host /almost/ everything, but route outgoing mail through Amazon SES. The pricing for…
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).
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#7IP reputation is a gamble, and there is no recourse. If you're lucky, awesome. But if you're unlucky and switching host isn't an option, you pretty much have to involve a large third party to act your behalf - there is zero appetite in the industry for interacting with individuals. The best solution I've been able to find is to self-host /almost/ everything, but route outgoing mail through Amazon SES. The pricing for…
Did switching your deliverer to SES have any effect on how clients like Gmail “tagged” your email? (Promotional category or something IIRC)
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#8IP reputation is a gamble, and there is no recourse. If you're lucky, awesome. But if you're unlucky and switching host isn't an option, you pretty much have to involve a large third party to act your behalf - there is zero appetite in the industry for interacting with individuals. The best solution I've been able to find is to self-host /almost/ everything, but route outgoing mail through Amazon SES. The pricing for…
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_FOR_MS byname ; \
msn.com SMARTHOST_FOR_MS byname ; \
live.co.uk SMARTHOST_FOR_MS byname ; \
hotmail.co.uk SMARTHOST_FOR_MS byname ; \
* DCsmarthost byname
host_find_failed = defer
same_domain_copy_routing = yes
no_more
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#9IP reputation is a gamble, and there is no recourse. If you're lucky, awesome. But if you're unlucky and switching host isn't an option, you pretty much have to involve a large third party to act your behalf - there is zero appetite in the industry for interacting with individuals. The best solution I've been able to find is to self-host /almost/ everything, but route outgoing mail through Amazon SES. The pricing for…
Did switching your deliverer to SES have any effect on how clients like Gmail “tagged” your email? (Promotional category or something IIRC)
Nope. The biggest impact on gmail was making sure I had DMARC, DKIM and SPF all set up correctly.
(I tried several other relay services like mailgun and those /did/ have noticeable impact - SES was the first one I tried that didn't, so I stuck with it).
Re: Self-hosting email in 2025 is easy actually (apart from M365)
#10I am in favour of the middle ground. Rather than expending effort self hosting email, which while plausible is unequivocally a heavy lift for most, make use of smaller providers such as Fastmail or Protonmail. Just please stop consolidating the internet.