It's possibly yet another issue relating to the long streak of problems seen the recent months by primarily self-hosters trying to reach people and businesses behind Outlook servers. The past few weeks a lot of my e-mails to friends and family using Hotmail have gone missing. All envelopes were OKd by Outlook servers, nothing bounced, e-mails just gone. My setup is clean, my network is clean.
I'm fine with providers imposing some default level of spam protection but as a user I'd like the option to disable it, even better if I can disable it per domain or sender. The old technique of adding the sender to your contacts doesn't work reliably anymore.
"The old technique of adding the sender to your contacts doesn't work reliably anymore."
An Outlook user first reaching out to you, and you replying and including the unique message-ID of their original envelope in your headers, doesn't affect anything either. Absurd. The whole situation is complete dog shit.