On going problem for me as well, I'm with Unchained, exactly the same issue. I spent half day with emails back and forth with Microsoft support and eventually was added to a whitelist. All was okay for a couple of months then it got blocked again, so I had to go through the process all again. Same pattern, okay for a few months then blocked again.
Why Microsoft are so dumb over this I don't know, its only them I've ever had this issue with. My IP appears on no block/black lists, and the number of emails I was sending to them was a couple a day if that to the same recipient, and DMARC and SPF all set correctly, hardly a sign of a spammer.
You can try sending an email to
[email protected], or using the portal at
https://sender.office.com/, this may tell you that you are not blocked by Office 365, and then provides a link to delist from hotmail/outlook domains. Any delist however doesn't seem to stick for long.
Upshot was I've had two friends quit using Hotmail/Outlook, they had found emails from a few different sources would never show up, so when I explained why that was likely, and that they are dropped and they would never know that was the case, i.e. not even in the SPAM folder, they didn't want to risk missing emails again so happy to move.
I've found though that companies using Office 365 for email, I'm never blocked from there, only from sending emails directly to @outlook.com @live.com and @hotmail.com.
Edited by E300 (Tue 31-Mar-26 14:04:19)