Outlook.com Dropping Forwarded Emails! Frustrated!

08. September 2013 · Write a comment · Categories: Hotmail, Outlook.com · Tags: , , ,
I am long time Outlook.com user and run my own email server (so I have a solid understanding of SPF, MX records, etc).
I forward certain accounts to Outlook.com (for reasons such as push email notification to mobile devices).

For the past few days, email forwarding DOES NOT WORK which is a major issue.

Here is another user complaining of the same issue:

I also posted at the bottom of this thread:

Long story short, this issue is sporadic.  At times the forwarding works, the next it does not.
Steps I have taken:
  1. My dedicated IP has a flawless reputation; I have rDNS setup; I contact the Outlook.com postmaster using the Microsoft form and they replied that there is no issue with delivering email.
  2. The only filter I have is to never put anything in the SPAM folder; mark everything as legitimate email.
  3. Outlook does NOT bounce emails; I did get one error: "Result: SMTP error from remote mail server after end of data: host mx1.hotmail.com [65.55.37.88]: 550 5.7.0 (COL0-MC2-F10) Unfortunately, messages from (192.65.243.59) on behalf of (chase.com) weren't sent. The domain's message authentication polic" but it appears to be Outlook.com INCORRECTLY checking SPF records on the original domain vs. checking SPF records on the sending IP/domain (meaning my server that I am forwarding to Outlook.com

It seems possible that a few of MX server's are handling forwarding different which is causing the inconsistencies in it working.
Please help.
Thank you.