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Ke, Liyiming, Li, Bo, Vorobeychik, Yevgeniy.  2016.  Behavioral Experiments in Email Filter Evasion.

Despite decades of effort to combat spam, unwanted and even malicious emails, such as phish which aim to deceive recipients into disclosing sensitive information, still routinely find their way into one’s mailbox. To be sure, email filters manage to stop a large fraction of spam emails from ever reaching users, but spammers and phishers have mastered the art of filter evasion, or manipulating the content of email messages to avoid being filtered. We present a unique behavioral experiment designed to study email filter evasion. Our experiment is framed in somewhat broader terms: given the widespread use of machine learning methods for distinguishing spam and non-spam, we investigate how human subjects manipulate a spam template to evade a classification-based filter. We find that adding a small amount of noise to a filter significantly reduces the ability of subjects to evade it, observing that noise does not merely have a short-term impact, but also degrades evasion performance in the longer term. Moreover, we find that greater coverage of an email template by the classifier (filter) features significantly increases the difficulty of evading it. This observation suggests that aggressive feature reduction—a common practice in applied machine learning—can actually facilitate evasion. In addition to the descriptive analysis of behavior, we develop a synthetic model of human evasion behavior which closely matches observed behavior and effectively replicates experimental findings in simulation.