Hotmail / Outlook.com / live.com swallowing e-mail.

A customer of mine contacted me the other day asking why one of my systems “password recovery” emails were not getting through.

I looked at the server logs and saw:

“SMTPC” 2116 10508 “2014-08-24 15:35:08.444” “65.55.37.88” “RECEIVED: 220 COL004-MC2F25.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft’s computer network is prohibited. Other restrictions are found at http://privacy.microsoft.com/en-us/anti-spam.mspx. Sun, 24 Aug 2014 07:35:10 -0700 “
“SMTPC” 2116 10508 “2014-08-24 15:35:08.445” “65.55.37.88” “SENT: HELO myserver.domain.org”
“SMTPC” 2156 10508 “2014-08-24 15:35:08.586” “65.55.37.88” “RECEIVED: 250 COL004-MC2F25.hotmail.com (3.20.0.138) Hello [78.129.999.999]”
“SMTPC” 2156 10508 “2014-08-24 15:35:08.586” “65.55.37.88” “SENT: MAIL FROM:<myaddress@mydomain.info>”
“SMTPC” 2136 10508 “2014-08-24 15:35:08.727” “65.55.37.88” “RECEIVED: 250 myaddress@mydomain.info….Sender OK”
“SMTPC” 2136 10508 “2014-08-24 15:35:08.728” “65.55.37.88” “SENT: RCPT TO:<myhotmailaccount@live.com>”
“SMTPC” 2144 10508 “2014-08-24 15:35:08.891” “65.55.37.88” “RECEIVED: 250 myhotmailaccount@live.com “
“SMTPC” 2144 10508 “2014-08-24 15:35:08.892” “65.55.37.88” “SENT: DATA”
“SMTPC” 2164 10508 “2014-08-24 15:35:09.035” “65.55.37.88” “RECEIVED: 354 Start mail input; end with <CRLF>.<CRLF>”
“SMTPC” 2164 10508 “2014-08-24 15:35:09.035” “65.55.37.88” “SENT: [nl].”
“SMTPC” 2160 10508 “2014-08-24 15:35:09.662” “65.55.37.88” “RECEIVED: 250 <!&!AAAAAAAAAAAYAAAAAAAAAD76P3dvGFxOgqGPn5iD4YbCgAAAEAAAABeTgegkxF9NpTMGUQDOnakBAAAAAA==@mydomain.info> Queued mail for delivery”
“SMTPC” 2160 10508 “2014-08-24 15:35:09.662” “65.55.37.88” “SENT: QUIT”
“SMTPC” 2124 10508 “2014-08-24 15:35:09.803” “65.55.37.88” “RECEIVED: 221 COL004-MC2F25.hotmail.com Service closing transmission channel”
“APPLICATION” 2056 “2014-08-24 15:35:09.811” “SMTPDeliverer – Message 1170347: Message delivery thread completed.”

(Above text edited to mask my real details).

Which shows that my server has connected successfully to Hotmail. Requested to send a mail from my domain and to my hotmail account successfully. Delivered the message content and Hotmail / Outlook.com have acknowledged that I’m done (Queued mail for delivery) and succesfully and cleanly disconnected from the SMTP session.

The message then fails to ever appear in my, or other users, hotmail mailbox! No bounceback, no error message in the SMTP session or anything, which is a bit annoying. Users (and my systems) don’t know that the message has been blocked or failed to reach the end user mailbox.
Hotmail’s SNDS service reports “All of the specified IPs have normal status.”

I set my server to bind it’s SMTP deliverer to a different IP in the same subnet and the problem continued.

I’m a bit baffled! I’ve submitted a request for support via their “Deliverability Issue Submission” form and will wait and see. (1260451346)

Edit: No response to my ticket but mail is flowing ok now, weird.

Update 2015: The latest address for the support form is probably http://go.microsoft.com/fwlink/?LinkID=614866 

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