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HotMail Delivery Status Notification (Failure)

I noticed that alerts from my server were failing for people using Hotmail.  Whenever one of the alerts was sent, I would get a notification back saying:


Final-Recipient: <account>
Action: failed
Status: 5.5.0
Diagnostic-Code: smtp;550 DY-001 Mail rejected by Windows Live Hotmail for policy reasons. We generally do not accept email from dynamic IP's as they are not typically used to deliver unauthenticated SMTP e-mail to an Internet mail server. maintains lists of dynamic and residential IP addresses. If you are not an email/network admin please contact your E-mail/Internet Service Provider for help. Email/network admins, please visit for email delivery information and support


I first tried removing my ip address from the dynamic records at, but I continued to get the failures.  I then dug in and figured out how to route authenticated email via gmail instead of direct to the customer's mail server anonymously.

Go to your SMTP Properties

In the Delivery tab, click the outbound security button and then set the basic authentication information. For gmail apps, your user name will be your full email address. Check the TLS encryption box.

Click OK and then click the Outbound connections button. Fill in port 587.

Click OK once again and then open the advanced options. Fill in for the smart host.

Click OK and OK, and you're all set. EZPZ

Posted: 4/11/2008 8:09:00 AM by Ryan Miller | with 0 comments
Filed under: SharePoint