> And even if you set everything up properly and host your email with a responsible host, Microsoft will still mark your mail as spam.
I did some experiments back when I ran my own mail. Sending from my mail server to my Microsoft account it not only marked everything as spam, it continued marking everything as spam after I marked a bunch of them as not spam.
After that, I tried also answering several of them and composing several new mails to send to my non-Microsoft email to see if Microsoft's spam system was smart enough to figure out that if I'm actively corresponding with someone their incoming mail should not be marked as spam. It was not smart enough.
I did some experiments back when I ran my own mail. Sending from my mail server to my Microsoft account it not only marked everything as spam, it continued marking everything as spam after I marked a bunch of them as not spam.
After that, I tried also answering several of them and composing several new mails to send to my non-Microsoft email to see if Microsoft's spam system was smart enough to figure out that if I'm actively corresponding with someone their incoming mail should not be marked as spam. It was not smart enough.
Then I tried whitelisting. Nope, still spam.