Thanks for your questions!

Thanks, everyone, who submitted questions to laura-questions@wordtothewise.com. We’ve gotten some great questions to answer here on the blog. I’m working through the emails and contacting folks if I have questions. I’ll be answering the first question on Wednesday.
I also did have someone harvest the address off the website and send me non-CAN SPAM compliant spam to it. I have to admit, I didn’t expect someone to harvest the address at all, but especially not within 12 hours of posting an address. Particularly someone who’s not harvested our contact address previously. I also am considering how much content I could get detailing taking the spammer to court in CA for violating CAN SPAM and the CA anti-spam statute.
 

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Email marketing ulcers for the holiday

I’ve mentioned here before that I can usually tell when the big ISPs are making changes to their spam filtering as that ISP dominates my discussions with current and potential clients and many discussions on delivery mailing lists.
The last two weeks the culprit has been Yahoo. They seem to be making a lot of changes to their filtering schemes right at the busiest email marketing time of the year. Senders are increasing their volume trying to extract that last little bit of cash out of holiday shoppers, but they’re seeing unpredictable delivery results. What worked to get mail into the inbox a month ago isn’t working, or isn’t working as well, now.
Some of this could be holiday volume related. Many marketers have drastically increased their mail volume over the last few weeks. But I don’t think the whole issue is simply that there is more email marketing flowing into our mailboxes.
As I’ve been talking with folks, I have started to see a pattern and have some ideas of what may be happening. It seems a lot of the issue revolves around bulk foldering. Getting mail accepted by the MXs seems to be no different than it has been. The change seems to be based on the reputation of the URLs and domains in the email.
Have a domain with a poor reputation? Bulk. Have a URL seen in mail people aren’t interested in? Bulk. Have a URL pointing to a website with problematic content? Bulk.
In the past IPs that were whitelisted or had very good reputations could improve delivery of email with neutral or even borderline poor reputations. It seems that is no longer an effect senders can rely on. It may even be that Yahoo, and other ISPs, are going to start splitting IP reputation from content reputation. IP reputation is critical for getting mail in the door, and without a good IP reputation you’ll see slow delivery. But once the mail has been accepted, there’s a whole other level of filtering, most of it on the content and generally unaffected by the IP reputation.
I don’t think the changes are going to go away any time soon. I think they may be refined, but I do think that reputation on email content (particularly domains and URLs and target IP addresses) is going to play a bigger and bigger role in email delivery.
What, specifically, is going to happen at Yahoo? Only they can tell you and I’m not sure I have enough of a feel for the pattern to speculate about the future. I do think that it’s going to take a few weeks for things to settle down and be consistent enough that we can start to poke the black box and map how it works.

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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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Content, trigger words and subject lines

There’s been quite a bit of traffic on twitter this afternoon about a recent blog post by Hubspot identifying trigger words senders should avoid in an email subject line. A number of email experts are assuring the world that content doesn’t matter and are arguing on twitter and in the post comments that no one will block an email because those words are in the subject line.
As usually, I think everyone else is a little bit right and a little bit wrong.
The words and phrases posted by Hubspot are pulled out of the Spamassassin rule set. Using those words or exact phrases will cause a spam score to go up, sometimes by a little (0.5 points) and sometimes by a lot (3+ points). Most spamassassin installations consider anything with more than 5 points to be spam so a 3 point score for a subject line may cause mail to be filtered.
The folks who are outraged at the blog post, though, don’t seem to have read the article very closely. Hubspot doesn’t actually say that using trigger words will get mail blocked. What they say is a lot more reasonable than that.

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