Cryptography is an essential component of America’s national security infrastructure. Billions of dollars are spent on cryptosystems every year, in both the public and private sector. Unfortunately, the field is rife with dubious claims, snake oil salesmen, and outright fraud. This paper highlights the importance of skepticism and critical thinking in the role of evaluating and procuring cryptosystems. We discuss our experiences in teaching future leaders about testing extraordinary cryptographic claims by asking hard questions, and show examples from our own experience. We believe that the rigorous application of skepticism and critical thinking in cryptography are absolutely essential to the wise use of America’s resources and the security of the nation.