I hate Google for effectively destroying the ability to self host an email server. You simply can't anymore. I mean, feel free to try, but be prepared to have half of your outbound messages dropped or rejected. And that's AFTER setting up SPF, DKIM, and DMARC.

@twylo i hate spammers for destroying that ability
@twylo one of the issues is that many/most mail services blacklist home ISP's dynamic ip ranges. it's pointless to even try on a home internet connection

@twylo I haven't had too much of a problem personally, *but*, that's because I use my ISP's relay for outbound mail, which presumably is more 'trusted'.

I know before that point it was hell, so I caved and went at least that far. :/

Yup. I gave up and bought email hosting service from Fastmail (who are *awesome*), but I self hosted for about 10 years before the GMail-pocalypse.

@twylo @kithop Hrm, was the mailserver hosted on a residential ISP?

Setting up Postfix on an OVH box seems to still work, though you do have to watch deliverability to Outlook, Google & Yahoo.

The latter two will send emails to spam, but hosted addresses are especially insidious as they'll accept emails, but throw them straight to /dev/null (or the Windows equivalent) with no trace in the user's inbox or spam.

@bikecurious @twylo Mailserver (and this server) are in my basement, racked up on a UPS, on Small Business class FttH. Technically a 'residental' ISP, though. Outbound relaying goes through them, but inbound delivery comes straight to me on standard ports.

I'm able to e-mail and keep in touch with friends and family on Gmail, other-ISP mail, etc. just fine.

I... don't know anyone with an address, though, so maybe that's it.

@kithop @twylo Some of the people and organizations I deal with have hosted mail, is what it is.

Deliverability issues have generally resolved themselves whenever I've spent a bit of time getting multiple users to pull us out of spam with the respective provider, we don't use a mail relay tho.

@bikecurious @twylo Oh! My work e-mail is an Office365 thing, not sure if that's the same - but I can e-mail things across to my own work e-mail just fine. I think we manage our own anti-spam stuff though, so that's likely why; probably a bit more lenient than what MS is using as defaults.

@bikecurious @twylo @kithop I had to submit some form to Microsoft before they'd accept email from my OVH box to hotmail. Only one person I wanted to email at hotmail, my sister, but yeah. Otherwise I've been ok, but my needs are pretty modest.

@georgieboy @twylo @kithop Huh, yet to encounter that, we've been sending a few emails a day to MS hosted addresses, when I started sending emails to debug it, our deliverability/missing mail issues magically ceased.

@bikecurious @twylo @kithop Maybe MS has relented? I got my box about 3 years ago, and there were definitely notes like “the whole OVH range is poison.” IP rep is definitely useful in my day job tho so I can’t blame them.

@twylo "Don't try send to them via IPv6" seems the current standard answer to that.

@twylo umm, not really? Of course the chain of trust and security extensions is wacky, but it takes about 4 hours of reading and an hour of testing to successfully send to gmail addresses give or take, and once they trust you it's effectively a olden ticket. There's many people that don't follow this though however and it's understandable.

@twylo I haven't self-hosted in ages and didn't realize this was a problem -- and it's a huge problem.

Also, your NeXT user pic is awesome and giving me the warm nostalgia-fuzzies for my first NeXTCube.

@twylo Honestly the biggest offender, for me, is Microsoft.

Like with Google I only get put into spam, but Microsoft put me on their block list the 20x time now, after revoking that ban with them manually each time >.>

And half the internet uses some sort of Microsoft mail/block list in the background and drops me.

@twylo fuck them with a knife. Depending on your definition of self-hosting, it can be made a bit better by switching providers. After years of deliverability problems on my server (spf, dkim etc) i accidentially sent an email to a test gmail account from a barely configured AWS EC2 instance. No spf, i doubt it even had matching PTR. Right to my inbox.

So your IP range matters. I did not want to route my personal data to Amazon, but setting up a smarthost at Linode helped.


I setup an email server using yunohost my 70% of mail reaches to inbox other host simply ban you.

Hotmail and Outlook ban new ip directly so that is an issue.


gmail is really notorious when it comes to what IP-range/network the sending server is located on.
ISP's like Vultr, DO and other is not considered "good" by them.

@selea @twylo I agree with this but to be fair an awful lot of spammers set up shop on those IP ranges...

I tried using AWS for my postfix send relay, but I found my messages going to spam most of the time, even after setting up DKIM, SPF and DMARC.

I had to resort to paying for business broadband at my home in order to get a static IP on a more trustworthy netblock.

@twylo @phessler Google is slowly destroying the internet and using their market share to further their own agenda

@twylo Well yeah, blocking mail from unregistered servers is what ended spam! 🙄

@twylo I've been hosting my own mail for nearly 20 years. Lately my stuff to gmail just gets silently dropped, but only intermittently. I have no way of knowing whether something's going to get through. Makes talking to HR about employment at companies who use Google for Domains a real challenge.

@twylo I've personally not had that much issue with Google when setting up an email server. The services that always give me the most grief are Yahoo's and Microsoft's.

@twylo Check out You can self-host there, I believe.

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