No cryptographic system is immune to attack, and CISSPs must understand the methods used to break or weaken them. In this episode, we explore cryptanalysis techniques including brute-force, dictionary attacks, chosen plaintext attacks, and side-channel analysis. We explain how poor implementation, weak keys, and outdated algorithms create vulnerabilities, and how to mitigate those risks through proper design and monitoring. Understanding these threats enables security professionals to assess crypto deployments with a critical eye and defend against evolving attack strategies.