How To Troubleshoot Hotmail Delivery Issues

If you are having Hotmail deliverability issues, you are not alone. Outside of Yahoo, Hotmail seems to be the most problematic domain especially for new email senders. Troubleshooting Hotmail delivery issues can be very challenging, and Hotmail is notorious for vaporizing your email without warning. So this brings up two issues.

  1. How do you know if your mail is landing in the spam box or, worse, being vaporized?
  2. If you find a Hotmail delivery problem, how do you correct it?

Detecting Hotmail Delivery Problems 

When searching for Hotmail delivery problems, the first place to look is in your logs. If you are seeing a large number of deferrals or failures to Hotmail, the Hotmail server responses in the log entries will give you an idea of what the problem is. It may be that you need to throttle back delivery to Hotmail, or make some other configuration change on your MTA or in DNS.

Next, consider setting up a Hotmail account or two and put the addresses on your mailing list. That way you can periodically log into your personal Hotmail account and see if your messages are making it to the inbox. (While you are at it – check your rendering.) This is easy to do yourself, however there are mailbox monitoring services available that will do this for you (for a fee) and will work with many of the important ISPs.

Fixing Hotmail Delivery Issues

Hotmail is also notorious for penalizing mail from unfamiliar IP addresses. If you are sending email from an IP that has not had much use recently for mail, you may run into a Hotmail deliverability issue. As you send more mail over the IP, and Hotmail becomes familiar with it, more of your mail should get through. Working with an email service like Socketlabs ensures that your IP addresses are properly warmed and monitored by our email professionals to give your email the best possible chance of hitting the inbox.

Another option to ensure successful Hotmail delivery is to sign up with SocketLabs to use our  whitelisting service. This security feature allows users to provide specific email addresses and/or domains that are permitted in the MAIL FROM SMTP protocol command issued during the mail relay process.  This added layer of security not only helps secure your email but it will help your deliverability as well. Contact us online if you’re interested in our whitelisting and email delivery  services.

Finally, here is a great resource from Microsoft for troubleshooting and overcoming Hotmail delivery issues, including a support contact:

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