This article discusses approaches to assessing the adequacy of a firm's cybersecurity posture. It proposes that assessments should be conducted in phases focusing on attack vectors, using skilled assessors with a variety of tools. Assessments should take a risk-based approach, ensure patch management is adequate, review defense-in-depth strategies, and use standards like NIST SP 800-53 to test the actual security state. The assessments aim to identify vulnerabilities and ensure perimeter defenses and compliance-based strategies are updated to address evolving cyber risks.