From traditional crime to terrorist attacks, surveillance and preparation by the perpetrators often increases the likelihood of attack success. Based on this premise, DHS Federal Protective Service used penetration testing to simulate an adversary’s perspective of federal facilities’ security and test the recommended risk management processes. Gain valuable perspectives on how trusted security measures can be exploited, then explore ways to use this knowledge to improve security planning and implementation. Come away with lessons learned from real (and sometimes scary) tests, while focusing on how to improve security assessments and measures.