My emails to hotmail/msn addresses are being rejected. Why?

You may find that when you send E-mail from your domain name to a user who has a Windows Live Hotmail E-mail address, you recieve a bounce-back and your email is rejected or even not recieved at all.� If rejected, the most likely reason given in the bounce-back is:

"Mail rejected by Windows Live Hotmail for policy reasons. Reasons for rejection may be related to content with spam-like characteristics or IP/domain reputation problems."

The Microsoft Windows Live Sender ID policy can sometimes identify legitimate messages as spam.  To help avoid this, you can set an SPF record for your domain, and look into Microsoft Sender ID policy here:

https://technet.microsoft.com/en-us/library/cc540496(v=ws.10).aspx

http://www.openspf.org/SPF_Record_Syntax

http://www.spfwizard.net/


NOTE: The previous resolution to this was to add your E-Mail address to the sender ID program at http://www.microsoft.com/mscorp/safety/technologies/senderid/default.mspx/ - however this link recently appears to be broken no matter where it appears on the Microsoft Tecnet website.  

UPDATE: You may have to contact Microsoft over missing email here, as the auotmatic sender id form is no lobger operational on their site. https://support.microsoft.com/en-us/getsupport?oaspworkflow=start_1.0.0.0&wfname=capsub&productkey=edfsmsbl3&locale=en-us&ccsid=636237899615295849

Microsoft has recently revised its policies and they are now more strict than ever before.� For example, they are removing HTML from email.� If you send out mail regularily, some hotmail recipients may mark your email as "junk" or "spam" via their email program which will result in your domain being blocked and your messages may not even be received.

How do I avoid having my messages marked as potentially dangerous?

To help prevent your messages from being identified as possibly fraudulent:
  • Always use valid, reputable URLs. Make sure it�s clear where the recipient will be taken and whether the destination is a valid website. 
  • Use the standard URL format. Avoid using IP addresses in the URL. 
  • Whenever possible, publish your Sender Policy Framework (SPF) records.
  • Do not link to known phishing sites. 
The MSN anti-spam policy and filters are very sensitive unfortunately and with their strict policies in place, this appears to be a huge problem for many in general.
 
Some of the deliverability issues are the result of sender-based software configurations. If you are running anti-virus software on your firewall or SMTP server, check for the setting �Internet E-mail Auto Protect� or �Internet E-mail Protection.� If this setting is enabled, disable it and try sending a test message to hotmail again. 
 
While we will advise and work to help resolve this, please also consider that this may require interaction with Microsoft, and the problem can only be resolved as fast as Microsoft respond.� 
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