An introspective behavior based methodology to mitigate e-mail based threats

The first part of this dissertation attempts to tackle the problem of detecting phishing e-mails before they reach users' inboxes. To begin with, shortcomings of existing spam filters toward classifying phishing e-mails are highlighted. To overcome them, a customizable and usable spam filter (CUSP) that detects phishing e-mails from the absence of personalized user information contained in them is proposed. However, as solely relying on the presence of personalized information as the criteria to detect phishing e-mails is not entirely foolproof, a novel machine learning based classifier that separates phishing e-mails based on their underlying semantic behavior is proposed. Experimentation on real word phishing and financial e-mail datasets demonstrates that the proposed methodology can detect phishing e-mails with over 90% accuracy while keeping false positive rate minimum. Also, feasibility of generating context-sensitive warnings that better educate the users about the ill-effects of phishing attacks is explored.;Classification techniques that operate on features confined to the phishing e-mails' body can be thwarted by using simple obfuscation techniques, which substitute spurious content appearing in them with seemingly innocuous characters or images. To address such scenarios, the second part of this dissertation takes the classification process a step further to analyze the behavior and structural characteristics of Websites referred by URLs contained in e-mails. Specifically, a challenge-response based technique called PHONEY is proposed to detect phishing Websites based on their inability to distinguish fake and genuine inputs apart. Experimental results based on evaluation on both "live" and "synthesized" phishing Websites reveal that PHONEY can detect almost of all the e-mails that link to live phishing Websites with zero false positives and minimal computation overhead. In a similar vein, this dissertation proposes a novel technique to identify spam e-mails by analyzing the content of the linked-to Websites. A combination of textual and structural features extracted from the linked-to Websites is supplied as input to five machine learning algorithms employed for the purpose of classification. Testing on live spam feeds reveal that the proposed technique can detect spam e-mails with over 95% detection rate, thereby exhibiting better performance than two popular open source anti-spam filters.;Information leaks pose significant risk to users' privacy. An information leak could reveal users' browsing characteristics or sensitive material contained in their e-mail inboxes to attackers allowing them to launch more targeted social engineering attacks (e.g., spear phishing attacks). The third part of this dissertation focuses on addressing these two facets of information leaks, i.e., information leak triggered by spyware and user by detailing out the limitations with the state-of-the-art detection techniques. In order to bring out the deficiencies in existing anti-spyware techniques, first, a new class of intelligent spyware that efficiently blends in with user activities to evade detection is proposed. As a defensive countermeasure, this dissertation proposes a novel randomized honeytoken based methodology that can separate normal and spyware activities with near perfect accuracy. Similarly, to detect inadvertent informational leaks caused by users sending misdirected e-mails to unintended recipient(s), this dissertation advances the existing bag-of-words based outlier detection techniques by using a set of stylometric and linguistic features that better encapsulate the previously exchanged e-mails between the sender and the recipient. Experimentation on real world e-mail corpus shows that the proposed technique detects over 78% of synthesized information leak outperforming other existing techniques.;Another important point to be considered while devising specialized filters to address each of the e-mail based threat is the need to make them interoperable. For example, an e-mail supposedly sent from a financial domain, but having an URL referring to a domain blacklisted for spam is very likely a phishing e-mail. Identifying sources of attacks helps in developing attack agnostic solutions that block all sensitive communication from and to misbehaving nodes. From this perspective, this dissertation explores the feasibility of building a holistic framework that not only operates in conjunction with intrusion detection systems (IDS) to block incoming and outgoing traffic from and to misbehaving nodes, but also safeguard the underlying e-mail infrastructure from zero-day attacks. (Abstract shortened by UMI.)...