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A comment on Self hosting is important. Parent comment

Re:Self hosting is important by ulrikrasmussen on Saturday July 24, 2021 @03:38PM (#27943816)
Not OP, but I have had deliverability problems with only one provider, and that is outlook.com. They seem to not care at all whether you have set up everything correctly (I pass all checks for reverse DNS, SPF, DKIM, etc., and I am not on any blacklists) but just have their own shitty whitelist of senders and throw everything else in spam. I had to throw in the towel and send through an SMTP proxy hosted by my VPS provider which solved all issues.

Please try to avoid using O365 as they literally are the main culprits that make self-hosting email a pain in the butt.

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Re:Self hosting is important by shaicoleman on Saturday July 24, 2021 @03:58PM (#27943955)
Wanted to say exactly the same thing.

I've set up everything according to best practices (SPF, DKIM, TLS, static IP for almost a year, reverse DNS, blacklist removal, spam checks).

I've also repeatedly contacted Microsoft support to get unblocked. All my requests to whitelist the IP in the last year or so have been ignored.

Microsoft is the sole bad actor I've encountered in more of a decade of self hosting email.

On principle, I've decided not to use a different provider, and users on Microsoft services will not get emails from me or from my websites.

This will only change if enough people complain. As a paying O365 customer, I'd encourage you to open support tickets that you're not receiving emails from some the smaller email servers, e.g. those hosted on DigitalOcean.

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Re:Self hosting is important by d110af5ccf on Saturday July 24, 2021 @09:49PM (#27945960)
I've had Outlook suddenly start sending family member's Gmail addresses to spam on multiple occasions. I truly don't understand what's going on there.
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Re:Self hosting is important by hifly on Saturday July 24, 2021 @07:23PM (#27945241)
same experience.. I run a small ISP. we only take paid clients so no one is a spammer (other than lost passwords). no delivery issues elsewhere. yet Microsoft filter absolutely everything into spam.... emails to support just get a "your request has been denied as not applicable" or some such junk
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