With a surge in the production of internet of things (IoT) devices, embedded development tools are becoming commonplace and the software they run on is often trusted to run in escalated modes. However, some of the embedded development tools on the market contain serious vulnerabilities that put users at risk. In this talk we discuss the various attack vectors that these embedded development tools expose users to, and why users should not blindly trust their tools. This talk will detail a variety reverse engineering, fuzzing, exploit development and protocol analysis techniques that we used to analyze and exploit the security of a common embedded debugger.