Explore a critical analysis of conventional penetration testing methodologies in this 20-minute conference talk from DefCamp 2019. Delve into the limitations and shortcomings of typical pentests, examining various attack vectors such as spearphishing, password exploitation, flash drive vulnerabilities, intranet weaknesses, and physical security risks like lockpicking and tailgating. Learn why these common approaches may fall short in providing comprehensive security assessments and gain insights into more effective strategies for identifying and addressing potential vulnerabilities in organizational cybersecurity.