I have exactly the same problem on my personal email server, ms silently drops my email! Their server replies with OK, but the email is nowhere to be found in the recipient’s inbox. Even if the conversation was initiated by the microsoft account and I merely reply to it, the email still disappears.
I’ve got everything setup properly, all test websites come up green, and google receives my email just fine. SPF, DMARK, DKIM, PTR, HELO are all setup correctly. This isn’t an isolated problem either, the ms forums are filled with people reporting similar problems.
One thing I've noticed too, make sure that your time is synchronized with an NTP server.
Even with a good reputation , MS drops emails with no error if you're a bit off.
"I have exactly the same problem on my personal email server, ms silently drops my email! Their server replies with OK, but the email is nowhere to be found in the recipient’s inbox."
Slightly tangential ... I heard recently that "proper" in-line responses (ie, not top-posting) is somehow penalized by Microsoft (or Exchange online or Outlook online or ... ?) and was advised to stop my very proper 1990s style in-line email quoting/responding and just top-post to avoid either non-delivery or something like the body of the email not being shown ...
Or something ?
Does anyone know what I am referring to and can shed some light here ?
Yeah, I only bottom-reply when I know (or can reasonably expect, e.g. on a mailing list) that the recipient is using a mail client that's not entirely brain damaged. Otherwise, I'll either top-reply or (if I really do want to respond to things in-line) actually say "See below for responses in-line" to clue in the recipient that yes, there's actually content in this email.
But yeah, that's usually more an issue with the mail client (or perhaps the mail server if it's being exceptionally stupid and modifying emails before final delivery). Top-replies became the norm for some god-forsaken reason, and now clients treat the quote and everything below it as entirely optional to display.
Same expirience here, but I must say it is becoming better since I have reverse resolve. Previously every mail went into spam. Regardless of SPF and DKIM.
I’ve got everything setup properly, all test websites come up green, and google receives my email just fine. SPF, DMARK, DKIM, PTR, HELO are all setup correctly. This isn’t an isolated problem either, the ms forums are filled with people reporting similar problems.