One of the ways in which attackers try to steal sensitive information from corporations is by sending spearphishing emails. This type of emails typically appear to be sent by one of the victim's coworkers, but have instead been crafted by an attacker. A particularly insidious type of spearphishing emails are the ones that do not only claim to come from a trusted party, but were actually sent from that party's legitimate email account that was compromised in the first place. In this paper, we propose a radical change of focus in the techniques used for detecting such malicious emails: instead of looking for particular features that are indicative of attack emails, we look for possible indicators of impersonation of the legitimate owners. We present IdentityMailer, a system that validates the authorship of emails by learning the typical email-sending behavior of users over time, and comparing any subsequent email sent from their accounts against this model. Our experiments on real world e-mail datasets demonstrate that our system can effectively block advanced email attacks sent from genuine email accounts, which traditional protection systems are unable to detect. Moreover, we show that it is resilient to an attacker willing to evade the system. To the best of our knowledge, IdentityMailer is the first system able to identify spearphishing emails that are sent from within an organization, by a skilled attacker having access to a compromised email account.
Phishing is a significant problem involving fraudulent email and web sites that trick unsuspecting users into revealing private information. In this paper, we present the design, implementation, and evaluation of CANTINA, a novel, content-based approach to detecting phishing web sites, based on the TF-IDF information retrieval algorithm. We also discuss the design and evaluation of several heuristics we developed to reduce false positives. Our experiments show that CANTINA is good at detecting phishing sites, correctly labeling approximately 95 of phishing sites. Each month, more attacks are launched with the aim of making web users believe that they are communicating with a trusted entity for the purpose of stealing account information, logon credentials, and identity information in general. This attack method, commonly known as "phishing," is most commonly initiated by sending out emails with links to spoofed websites that harvest information. We present a method for detecting these attacks, which in its most general form is an application of machine learning on a feature set designed to highlight user-targeted deception in electronic communication. This method is applicable, with slight modification, to detection of phishing websites, or the emails used to direct victims to these sites. We evaluate this method on a set of approximately 860 such phishing emails, and 6950 non-phishing emails, and correctly identify over 96 of the phishing emails while only mis-classifying on the order of 0.1 of the legitimate emails. We conclude with thoughts on the future for such techniques to specifically identify deception, specifically with respect to the evolutionary nature of the attacks and information available.