Jason’s Random Thoughts

Over the last several months I’ve been noticing a growing trend where people are not receiving my emails in a timely fashion, if at all, when the destination is a Hotmail, GMail or Yahoo mail account. At first I had thought this might have just been a case of quick fingers, where someone accidentally deleted my email while cleaning their inbox of spam. Lord knows I’ve done this a few times and had to retrieve a message from the garbage bin, but how often can this really happen? However, yesterday I received a happy little email from Hotmail telling me that my messages were no longer welcome so long as they came from my j2fi.net or TheCarbonBlog.com domains.

Here is the main body of the message I received:

This message was created automatically by mail delivery software.

A message that you sent could not be delivered to one or more of its recipients. This is a permanent error. The following address(es) failed:

xxxxxxxx-at-hotmail.com
SMTP error from remote mail server after MAIL FROM:<jason-at-j2fi.net> SIZE=25553:
host mx2.hotmail.com [65.54.xxx.xxx]: 550 OU-001 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. If you are not an email/network admin please contact your E-mail/Internet Service Provider for help. Email/network admins, please visit http://postmaster.live.com for email delivery information and support

—— This is a copy of the message, including all the headers. ——

What? Me? Spam?

Suffice to say, I wasn’t too impressed with the message, but I was happy to see something come back from Hotmail that tells me what I need to do. There’s nothing worse than sending an email only to have it completely disappear in the ether that is the internet.

So What Can We Do?

There seems to be two primary options for resolving this matter. One is to create a SenderID and associate it with the DNS entry of your mail server, and the other is to get on an email White Listing service such as Sender Score. Since email plays a critical role in my online communication, but I can’t justify a huge cash outlay, I decided to initially go with a Sender ID. Although I would love to set up an account with Sender Score, the $400 application fee is just a bit more than I can realistically afford to spend for the sake of a dozen emails to the major web-based email providers every month.

To that end, I’ve included the step-by-step of the procedures I followed, as well as the amount of time that passed before my site was accepted by SenderID and updated accordingly.

What Is Sender ID

According to the Microsoft website, Sender ID is an email authentication protocol that helps address the problem of spoofing and phishing by verifying the domain name and IP addresses of the email server sending the messages. Apparently, this has already been adopted by over ten million domains and is proving to be quite useful.

In their framework paper, they advise us to make an SPF (Sender Policy Framework) record and attach it to the DNS text file on our mail server. Since this is all Greek to me, I was happy to see that Microsoft does offer a SPF Creation Wizard that will guide us through the process and provide the relevant information that we need to paste into the text file.

All in all, the questionnaire took less than five minutes to complete and at the end we’re given the necessary text that should be added to our DNS records. For anyone that is using shared hosting with an email package, you will likely need to create a support ticket that includes the information supplied by the SPF wizard. If you’re running your own server, then I hope you know how to modify your DNS file, as this is different for almost every Operating System (but I can help out if you’ve never done it).

The Waiting Game

After making the changes to your DNS record, you will need to wait anywhere between two hours and a day for the new information to propagate through the web. Once this is done, any web server that is configured to check for a Sender ID will query the SPF record on your email server and compare it to the record found on the Sender ID servers. So long as they both match, your email will be considered authenticated and the message will arrive in the destination inbox without a problem. That said, there are still opportunities for your domain to be removed from the Sender ID program if too many people mark your messages as being spam.

I had the changes made to my email server before leaving for work this morning and, after coming home, I was pleased to discover that Hotmail, GMail and Yahoo Mail were all accepting my messages once again. Hopefully I will not need to invest a huge sum of money to get on some of the better-regarded email White Lists but, if I do, then I’ll be sure to fight it tooth and nail.

Have you had problems sending emails from your own server in the past? How have you corrected the problem?