The world has seen a seismic shift from browser-based web applications to GUI-rich semi-thick client applications running on handheld mobile devices. In the browser world, the industry had placed a great deal of time and energy towards providing users visual cues to indicate the level security and trust that their data being transmitted to the remote server is protected and not falling into the hands of unintended recipients. In the mobile device world, these visual cues are mostly nonexistent, resulting in the inherent trust that the underlying APIs are ensuring a level of security before transmitting a users sensitive data. In our research, we tested the most popular apps on both the iOS and Android platforms. We ran each app through a data transmission assault course that contained various historic, contemporary, and obscure SSL attacks and documented the results. In this presentation, we will discuss and demonstrate flaws at both the application an OS layer that need to be addressed by both the mobile app developers and well the mobile device manufactures. A utility called "SSLizzard" will also be released for use by mobile application developers to test their mobile apps and their behavior against SSL-based attacks discussed in this talk.