Filtering adjustments at Hotmail

I’ve been seeing a lot of discussion on various fora recently about increased delivery issues at Hotmail. Some senders are seeing more deferrals, some senders are seeing more mail in the bulk folder. Some senders aren’t seeing any changes.
This leads me to believe that Hotmail made some adjustments to their filtering recently. Given some senders are unaffected, this appears to be a threshold change or a calculation change, tightening up their standards. The changes have been around for long enough now it does look like the filtering is working as intended and Hotmail is not going to roll these changes back.
So what can you do to fix delivery of mail that was good enough at Hotmail a few weeks ago and now isn’t?

  1. Look at your data hygiene. Do you have older addresses that haven’t responded in any way recently? Try removing that data from your mailings for a week or two and see if that improves your delivery.
  2. Check your content for URLs that might be advertised or spammed in mail from IPs other than your own. Use domains you have complete control over in all your mail, both for links and anywhere in the text.
  3. Contact recipients through a non email channel and ask them to add your address to their address book.
  4. Look at performance of your lists per acquisition channel, maybe one of your acquisition processes is giving you poor data. Removing these addresses may improve your overall reputation and get your mail into the inbox.

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SPF records: not really all that important

I’ve been working through some Hotmail issues with a client over the last few months. One of the things that has become clear to me is how little Hotmail actually does with SPF records. In fact, Hotmail completely ignored my client’s SPF record and continued to deliver email into the inbox.
This isn’t just a sender that had a “well, we think most of our email will come from these IPs but aren’t telling you to throw away email that doesn’t” record. In fact, this client specifically said “if email doesn’t come from this /28 range of email addresses, then it is unauthorized and should be thrown away.” The email was being sent from an IP outside of the range listed in the SPF record.
As part of the process involved in fixing the delivery problems, I had the client update their SPF record and then I enrolled their domain in the SenderID program at Hotmail. This didn’t have any effect, though. Hotmail is still not checking SPF for this client. When I asked Hotmail what was going on they said, “We do not do lookups on every sender’s mail.”
So, there you have it folks. The last bastion of SPF/SenderID has abandoned the technology. Even a totally invalid SPF record doesn’t matter, mail can still reach the inbox at Hotmail.

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Reputation monitoring sites

There are a number of sites online that provide public information about reputation of an IP address or domain name.

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Content based filters

Content based filters are incredibly complex and entire books could be written about how they work and what they look at. Of course, by the time the book was written it would be entirely obsolete. Because of their complexity, though, I am always looking for new ways to explain them to folks.
Content based filters look at a whole range of things, from the actual text in the message, to the domains, to the IP addresses those domains and URLs point to. They look at the hidden structure of an email. They look at what’s in the body of the message and what’s in the headers. There isn’t a single bit of a message that content filters ignore.
Clients usually ask me what words they should change to avoid the filters. But this isn’t the right question to ask. Usually it’s not a word that causes the problem. Let me give you a few examples of what I mean.
James H. has an example over on the Cloudmark blog of how a single missing space in an email caused delivery problems for a large company. That missing space changed a domain name in the message sufficiently to be caught by a number of filters. This is one type of content filter, that focuses on what the message is advertising or who the beneficiary of the message is. Some of my better clients get caught by these types of filters occasionally. A website they’re linking to or a domain name they’re using in the text of the message has a bad reputation. The mail gets bulked or blocked because of that domain in the message.
One of my clients went from 100% inbox every day to random failures at different domains. Their overall inbox was still in the 96 – 98% range, but there was a definite change. The actual content of their mail hadn’t changed, but we kept looking for underlying causes. At one point we were on the phone and they mentioned their new content management system. Sure enough, the content management company had a poor reputation and the delivery problems started exactly when they started using the content management. The tricky part of this was that the actual domains and URLs in the messages never changed, they were still clickthrough.clientdomain.example.com. But those URLs now pointed to an IP address that a lot of spammers were abusing. So there were delivery problems. We made some changes to their setup and the delivery problems went away.
The third example is one from quite a long time ago, but illustrates a key point. A client was testing email sends through a new ESP. They were sending one-line mail through the ESPs platform to their own email account. Their corporate spamfilter was blocking the mail. After much investigation and a bit of string pulling, I finally got to talk to an engineer at the spamfiltering company. He told me that they were blocking the mail because it “looked like spam.” When pressed, he told me they blocked anything that had a single line of text and an unsubscribe link. Once the client added a second line of text, the filtering issue went away.
These are just some of the examples of how complex content based filters are. Content is almost a misnomer for them, as they look at so many other things including layout, URLs, domains and links.

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