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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. :/

@kithop
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 Outlook.com 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 Outlook.com address, though, so maybe that's it.

@kithop @twylo Some of the people and organizations I deal with have Outlook.com 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.

@starbreaker @twylo "Half" is giving them a good benefit. More like 90%, even sometimes when you're on that person's contact list.
@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.

@twylo

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.

@twylo

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...

@twylo
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

I have my own email server since last century.
The personal domain I currently use created on 2002.
So the email I am using is 17 years old, which is older than gmail.
Nothing can stop you to have a personal email server.
@twylo

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

@twylo not true, I mean, fuck google BUT I have my own mailserver working just fine without any melodrama.

@gonzalo @twylo I'm good, thanks. I meant: I also don't have any issues with Gmail, etc. with my own mailservers. 😉

@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 sdf.org. You can self-host there, I believe.

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