In George Orwell’s `nineteen eighty-four: A novel', there is fear regarding what “Big Brother”, knows due to the fact that even thoughts could be “heard”. Though we are not quite to this point, it should concern us all in what data we are transferring, both intentionally and unintentionally, and whether or not that data is being “leaked”. In this work, we consider the evolving landscape of IoT devices and the threat posed by the pervasive botnets that have been forming over the last several years. We look at two specific cases in this work. One being the practical application of a botnet system actively executing a Man in the Middle Attack against SSH, and the other leveraging the same paradigm as a case of eavesdropping on Internet Protocol (IP) cameras. For the latter case, we construct a web portal for interrogating IP cameras directly for information that they may be exposing.