I have a server that I’m using to send mail via postfix. It’s delivering to other major providers like gmail and icloud, but it’s not sending to any of microsoft’s domains.
A bit of background, I initially didn’t realise I needed to do anymore work after installing postfix, so I was sending messages without any authentication, after a couple of days they stopped reaching my personal hotmail account.
I’ve since sorted out the SPF, DKIM, DMARC and PTR records so that it’s a much more legit operation, but alas, nothing is reaching my hotmail account.
If you need more information to diagnose the problem, please let me know and I’ll provide.
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One of the first things I’d recommend would be a scan on your IP and Domain against blacklists. This will let you know if blacklists are the issue.
Hotmail is pretty picky about how fast you send transactions. As @hansen said, the mail log should give you the reason that mail cannot be delivered and from there we could provide some help in addressing the problem.
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