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 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. :/

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@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.

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