Can You Say [Phrase” in E-Mail?

Every once in a while, a certain discussion arises in the ClickZ offices. It always leaves me dissatisfied. The conversation starts like this: “I’m thinking about ’[insert phrase here”’ for a headline. Do you think that would make it past spam filters?”

Judging from the amount of email we get on this subject, talks along those lines occur in offices all over the place — anywhere where people write copy intended to wing its way into inboxes. The challenge is to make sure email really makes it to its final destination and isn’t filtered into bulk folders or a black hole en route. (AOL’s Brian Zwit, at this week’s ClickZ E-Mail Strategies conference, referred to mail blocked by the ISP itself as “absorbed.” It isn’t bounced, but it isn’t delivered either. Of course, neither sender nor recipient are the wiser.)

According to a recent study by Assurance Systems, a company that deals with delivery issues, approximately 15 percent of permission-based email doesn’t make it into inboxes at the top 10 email account providers. What can you do to make sure your mail gets through? There are steps you can take.

Get Permission

Spammers, stop reading now! That was a joke, but, speaking seriously, step one is to make sure you’re scrupulously following email best practices. ISPs, enterprises, and individuals are undeniably becoming more aggressive in the fight against spam. Legitimate marketers are often caught in the crossfire. That’s no reason to side with the spammers. It’s in legitimate marketers’ best interests to ensure spam blocking works effectively. When it does, permission-based messages land in relatively uncluttered email boxes.

Note the term “permission-based.” Permission means opt-in or, better still, double opt-in. Keep records of how and when you got permission and the IP address of the computer user who gave it to you. Make sure any list you use is scrupulously clean. You might consider writing a “cleanliness clause” in contracts with third-party list providers. Even one fake address on a list can derail an entire campaign if that address was established for a “probe” filtering technique, such as Brightmail’s. Brightmail creates fake “probe” addresses. The company tracks any messages those addresses receive. These are automatically tagged as spam. Brightmail makes the spam call for Hotmail, EarthLink, Verizon, and other major ISPs. Hit a probe, your campaign is “absorbed.”

Secure Your IP Address

After you’ve got the permission thing straight, there’s technology. In some cases, this involves your email service provider, if you’re using one. The basic thrust here is to make sure your email really comes from where it appears to come from. Make sure it’s configured for reverse DNS lookup. Enrique Salem, Brightmail’s CEO, says 90 percent of email caught in Brightmail probes is untraceable. In other words, the email headers are fake or misleading.

Your email must be sent from a “clean” IP address, one not being used by others to send spam. It should be firewalled or otherwise safeguarded to ensure it’s secure and can’t be used as an open relay. To view IP addresses listed in blacklist databases, you can try Declude’s list, DNSstuff.com, or Sam Spade.org.

Watch Your Language

Finally, the issue so hotly debated around here: what text is likely to land you in trouble (or bulk-mail folders). It’s easy to test if your message lands in, say, your personal Yahoo “bulk” folder. It’s more difficult to determine why or what to do about it.

Though officially gazillions of spam filter programs are now in circulation, no one is eagerly stepping up to tell you what words are no-nos. That would help spammers, after all. The most easily available (open source) software available that can tell you that is SpamAssassin. You need to be technically inclined to set it up, but, when it’s configured, you should be able to send an email through the system and see how it scores in terms of “spamminess.” (Here are some reports on some outrageously spammy emails.) It will tell you how an email scores and what triggers might set off alarms.

A more labor-intensive way to get an idea of the dangerous words and phrases is looking at SpamAssassin’s list of rules. Each rule is weighted by its likelihood to indicate spam. Unfortunately, must-haves (such as an unsubscribe address) can actually help rack up the points.

Although the list of rules may be overwhelming, George Bilbrey, CEO of Assurance Systems, says a study the company undertook recently shows high SpamAssassin scores are, indeed, correlated with message nondelivery.

“If your scores are high on SpamAssassin, you are going to have delivery problems,” says Bilbrey. “Up until about [a score of” 10 there was a correlation, but it was sort of shallow. Once you hit 15, it really goes off the cliff.”

Assurance Systems knows because the company set up several test emailboxes on each of the major ISPs. It checked to see if messages got through. You can do that, too (or you can hire Assurance Systems to do it for you).

Talk With ISPs

If you take care of all the above and tests show you still have problems, it may be time to take it up with the ISPs. America Online’s postmaster page offers tips on how to avoid being blocked on AOL. Brightmail says you can send examples of unjustly blocked mail to [email protected] and the company will check it within minutes.

It’s become a fairly complex game. Hopefully, a combination of industry initiatives, federal legislation, and technological solutions will soon bear fruit. If you’ve got an email newsletter that needs to go out tomorrow, though, these hints may help you navigate the dizzying array of hurdles now standing in your way.

Happy (permission-based) emailing!

Don’t miss ClickZ’s Weblog Business Strategies in Boston, June 9-10.