One common thread runs through a recent wave of (initially, successful) targeted malware attacks I've investigated: The attackers communicated with their targets, personally, using social engineering in real-time, in order to lay the groundwork for the rest of the attack to succeed. Throughout the course of several post-breach investigations, it became apparent that -- for a certain kind of target and a particular class of attacker -- engaging the victim in direct conversation was far more effective at assuring the target infected their computer than crafting a believable-looking "malspam" email that would "fool" the target into clicking a link or opening a file.

The attackers did not need to be charismatic for the technique to succeed. In fact, so long as the attacker "got into character" and treated the interaction as a normal, everyday event (from their perspective), the targets went along for the ride, and in many cases, self-infected with malware that was capable of snooping through their most sensitive files. In this session, we'll discuss both the social engineering and technical aspects of the attacks, and why this combination of tactics is particularly dangerous and hard to defend against.