Radar Hill Blog

Hotmail’s not looking so cool

The old Hotmail logo, with blue arrows wrapping around a mail envelope, and the rainbow MSN butterfly.We’ve received a number of complaints lately from clients who can’t seem to send emails to customers who have a Hotmail email address.

If they try, they receive a bounce back message containing the following:

550 SC-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.

Not very reassuring, and understandably upsetting for our clients. Wanting to fix this issue if at all possible, we checked Hotmail’s Troubleshooting Guide for bounced messages. There were a number of things listed for mail server managers (us) to check, but all of our settings were just as they should be.

Further down in the FAQ, we saw the question “Does Windows Live Hotmail operate an “allow list” that I can get on?”:

No. An “allow list” (a.k.a. “white list”) is essentially a “free pass” which allows emails from certain senders to bypass junk email filters and other precautions. Windows Live Hotmail evaluates all inbound email for malicious content. You can find out more about our filtering processes here. We do, however, partner with Return Path, Inc. who helps ensure the legitimacy of certain senders via their Sender Score Certified program. This program allows Windows Live Hotmail to exercise greater assurance about mail from certified senders in good standing. You can learn more about the Sender Score Certified program here.

So we went to ReturnPath’s Sender Score website, where they have a convenient page where you can test whether your IP is on their blacklist (ie. would be blocked as spam). We input the IP addresses of the affected clients’ websites and checked out their score. (If you don’t know your IP address, you can get it here by putting your website address in the box at the top of the site. Or if you want to feel smart, you can do it the fancy way using ping.)

All of the IPs we checked were reported as not being on ReturnPath’s blacklist. Next we checked the websites’ general Sender Score, only to be told, “Insufficient Email Seen – We have not seen a sufficient volume of email from [client’s IP Address] to calculate scores or delivery rates.” Finally, we checked a list of global spam blacklists to make sure we weren’t blocked by another service that might be influencing Hotmail.

Nothing.

So ReturnPath says we aren’t actually blocked, but Hotmail says we are. Hotmail’s suggestion for fixing the problem is to check our standing with ReturnPath, which turns out to be fine. By this point we were getting a little confused.

After checking the support pages, we quickly discovered that there’s no way to directly contact Hotmail to discuss issues like this. One of our affected clients contacted ReturnPath by phone on his own initiative, only to be told that his site was definitely not on their blacklist and that the issue must be on our end. But how can we be causing the issue when Hotmail is clearly receiving the message and is the one sending the warning back? We’re pretty stumped on that too, to be honest.

Yet another affected client contacted ReturnPath on their own and reported the following:

Hotmail says that if we are blocked we need to take it up with ‘Return Path’ which is the 3rd party controlling their blocked list. They want us to pay (in best case scenario) an application fee of $200 plus a yearly fee of $440.

Yup, that’s right. After blocking completely valid emails with no spam content for no apparent reason, and repeatedly stating that we aren’t on their blacklist so there isn’t any reason we should be blocked, ReturnPath wants our clients to pay to guarantee that they won’t be blocked by their own service. This instead of, you know, actually correcting the issue.

By this point clients are understandably asking us, “What can we do?” A good number of their customers use Hotmail, and not being able to send any mail to them is a big issue. And we’re more than a little upset to have to shrug, hold up our hands, and say “Try sending from a different email address.”

There are a few other tips that you can follow in an attempt to get your messages through again, but there’s a problem with them — most of them rely on Hotmail’s review of your message in order to bring down your spam score. If Hotmail has already got you marked down as a spammer, it likely isn’t going to be reviewing those messages in the first place — it’s just going to throw them out.

We wish we had a better solution, but we don’t. And rest assured that this isn’t the first time, or likely the last. Even Gmail accounts have had issues sending to Hotmail addresses, at least as recently as last year.

All we can do is hope that Hotmail hears the outcry of its users (and those trying to reach them) and corrects the situation as soon as possible.

In the meanwhile, I think I’ll stick with my personal Gmail account.

About Kendra

Self-taught and Google-trained, Kendra is Radar Hill's content expert certified in both Google AdWords and Analytics. Armed with a wide array of testing and analysis tools, she's always researching the latest SEO trends and works hard to make sure that websites and online marketing campaigns deliver a top-notch customer experience.
This entry was posted in Security, Software & Apps, Technology and tagged , . Bookmark the permalink.

Comments are closed.