The threat of insiders stealing valuable corporate data continues to escalate. The inadvertent exposure of internal data has also become a major problem. Data loss prevention systems are designed to monitor and block attempts at exposing sensitive data to the outside world. They have become very popular, to the point where forensic investigators have to take these systems into account. This chapter describes the first experimental analysis of data loss prevention systems that attempts to ascertain their effectiveness at stopping the unauthorized exposure of sensitive data and the ease with which the systems could be circumvented. Four systems are evaluated (three of them in detail). The results point to considerable weaknesses in terms of general effectiveness and the ease with which the systems could be disabled.