How to Filter with Finesse

With somewhere between 80 percent and 95 percent of all Internet messages now consisting of spam, phishing attacks and e-mail based worms, organizations have been forced to filter their incoming mail more aggressively than ever before.

E-mail filtering systems are faced with the Herculean task of separating out the bad mail from the good -- and doing it fast enough so that the mail doesn't back up. Computer scientists call this a "recognition task" and say that e-mail filtering is one of the most challenging of such tasks that's ever been devised. The job just keeps getting harder and harder every day, as the bad guys adapt their messages to make them more closely resemble legitimate mail. The cost of letting through a bad message can be high: A single phishing message, successfully passed to one of your users, can compromise your internal systems. Even ordinary spam annoys your users and can cause employees to miss important messages. Spam must be stopped.

But as a CSO, you have another job as well: You need to make sure that your organization's e-mail filtering system isn't filtering out the wheat with the chaff. That's because the cost of a legitimate mail message gone missing can be equally high. More and more, I hear of business opportunities that fall through because an unexpected e-mail message was delivered to a junk mail box or silently dropped. The senders of these messages thought that the recipients weren't interested, but in fact the messages simply never arrived. Legitimate mail must not be stopped. So even as CSOs filter aggressively, the trick is to find the right combination of tools and techniques to keep the real messages from getting swept into the spam box. While many options are available today, a closer examination leads me to think that ultimately digital signatures will prove necessary if we are going to keep spam from turning e-mail into a nonviable communication medium.

Rejection rates

There are several technical metrics that a CSO can use when trying to evaluate mail-filtering systems. Two of the most common are the false-negative and false-positive rates. A false negative might be a piece of spam that the system lets through that it shouldn't; a false positive is a message that is blocked, even though it is legitimate.

Unfortunately, there aren't a lot of reliable sources for these metrics. In part, that's because the metrics are different for every user of a given filtering system. A user who has posted her e-mail address to a popular online discussion will receive a lot of spam, and probably a greater variety of spam, than a user who has been circumspect with his online identity.

As a result, that first user will probably see more messages sneaking through the filters and therefore experience a higher false-negative rate. Also, filtering systems do not behave in a consistent fashion. In one case I am familiar with, a researcher at MIT sent two separate one-line text messages to a collaborator in Europe. One of those messages ended up in the collaborator's spam box; the other went to the inbox. How do you debug randomness like that?

Earlier this year, a company called Pivotal Veracity published a 33-page study on the prevalence of false positives in antispam systems operated by three of the largest Web mail providers. Pivotal Veracity is itself an e-mail consulting service (more on it later), which might have led some people to dismiss the research. But the company's methodology was very good and the results were interesting and important.

To conduct its study, the researchers at Pivotal created Web mail accounts at Google, Microsoft and Yahoo. They then signed up for e-mail newsletters from 100 randomly chosen corporations, nonprofits and governmental agencies. Then, over the next six weeks, the researchers checked the mailboxes to see if mail from those senders got delivered to the inbox or the spam box.

What makes this kind of study challenging is that the researchers didn't know if the organizations were actually sending mail. In fact, mail was received from only 90 of 100 purported sending organizations. This could be because the other 10 never sent mail at all. Alternatively, it could be because the incoming mail was deemed so offensive that it was just dropped, rather than put in a spam box. For example, some e-mail providers will automatically drop phishing attacks directed against PayPal or Citibank customers: The attacks seem so authentic that users will see the messages in their spam folders, assume that the antispam software has made a mistake and click on the links! So the e-mail providers prevent such messages from even getting to the spam box. It's conceivable (however likely or unlikely) that this kind of aggressive filtering could explain some of the 10 missing newsletters.

Unless our systems for filtering mail get dramatically better, we face the very real possibility that e-mail might become a lost communication medium.

Ignoring that missing 10 percent, Pivotal found that e-mails from 54 percent of the legitimate mail senders -- real companies from whom mail had been requested -- had at least some of their messages identified as spam and delivered to the Web mail provider's junk mail box. This is an astoundingly high false-positive rate! Even more troubling was how those numbers break down.

Pivotal evaluated the effectiveness of the sender policy framework (SPF) e-mail sender authentication system. SPF allows organizations to electronically publish the IP addresses of their e-mail servers: Antispam systems can then reject incoming mail if it doesn't come from the correct server. Citibank, for example, publishes an SPF record for its domain, which states that mail from that domain should come from the IP address beginning 192.193.195 or 192.193.210, or else that e-mail should be discarded. In theory, this prevents a hacker in Yemen from sending e-mail that claims to be from Citibank -- at least, with SPF it is possible for a mail filter to automatically detect this mail and discard it.

But what Pivotal discovered is that SPF had no impact on whether e-mail was identified as spam. Roughly 75 percent of companies in the survey implemented SPF, but there was no significant difference in the false-positive rates of those companies sending mail with SPF and those that did not.

Another troubling finding is Pivotal's evaluation of the so-called e-mail accreditation programs, such as those offered by Truste and Bonded Sender. These programs are designed to help businesses improve the chances that their mail will actually get delivered. But Pivotal found that companies that used Truste or Bonded Sender actually had a higher incidence of false positives than those that did not subscribe -- 57 percent of Truste members suffered false positives, as did 55 percent of Bonded Sender users, versus 53 percent of nonusers.

Pivotal's assessment of Bonded Sender and Truste has come under some criticism. For example, only 13 of the 100 companies that Pivotal tested were members of Bonded Sender. Also, the Bonded Sender seal is ignored by Gmail and Yahoo -- only Hotmail honors it. While these might be valid criticisms of the study, the criticism itself seems to imply that Bonded Sender and other seal programs are not tremendously significant in today's e-mail landscape. "Accreditation is intended for those senders who have no reputation," says Deirdre Baird, Pivotal's president. But today, most antispam systems base their decisions not on whether the sender is accredited but on that sender's reputation. A sender's reputation is determined by how users tend to respond to messages from that sender. That is, most Web mail companies have a button that allows the recipient to "report spam." If a lot of users report that messages sent by a particular company are spam, then future messages from that company are more likely to be identified as spam.

The problem with using this kind of collaborative filtering approach to fighting spam is that consumers click that "report spam" button for a variety of reasons. A message might not be truly spam, but consumers might click "report spam" because they want to unsubscribe from a mailing list for which they've previously signed up. And since consumers repeatedly have been told not to reply to spam or click "unsubscribe" links, really the only thing left for them to do is click the "report spam" button.

Pivotal calls itself a Deliverability Service Provider, working with organizations that send e-mail to tailor messages and mailing practices to increase the chances that mail will successfully get through. For example, says Baird, Pivotal can work with e-mail designers to make sure that HTML messages actually validate according to the standards specified by the World Wide Web Consortium (e-mail with HTML that doesn't validate has a higher chance of being marked as spam). Other companies in this space include eDiagnostix, EnhanceRate, Piper Software and Return Path.

The way forward

While many choices are now available to help companies fight incorrect spam filtering, the complexity and difficulty surrounding this issue is bad news for CSOs. Spam is almost certain to increase in coming years, and the hostility of e-mail-borne threats is sure to increase as well. But unless our systems for filtering mail get dramatically better, we face the very real possibility that e-mail might become a lost communication medium -- much in the way that CB radio was lost in the 1970s. But unlike CB radio, businesses and individuals now depend on e-mail. Every time e-mail becomes less effective, it costs us all dearly.

My suspicion is that the only way to satisfactorily solve the problem of e-mail reliability is for companies sending mail to sign their messages with the S/MIME digital signature standard. Once that starts happening, antispam systems can be modified to let through mail that is signed by senders known to be legitimate. Spammers can make their content as close to the content of a legitimate sender as they want, but they can't fake a digital signature. As a result, digitally signed mail probably represents our last, best chance for saving e-mail.

-- Simson Garfinkel, PhD, CISSP, is spending the year at Harvard University researching computer forensics and human thought. He can be reached at

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