Cybersecurity teams face a crucial question of identifying vulnerabilities before they can be exploited by attackers, and to address this, organizations rely on penetration testing, which can be both automated and manual. Automated penetration testing uses tools to scan systems quickly and identify known vulnerabilities, but it has limitations such as false positives, poor signal-to-noise ratio, and lack of context, which can lead to missed complex issues. Manual penetration testing, on the other hand, involves skilled security professionals who think like attackers and use their technical expertise and creative problem-solving skills to find subtle vulnerabilities that automated tools may miss. The most effective approach is to combine both automated and manual testing methods, using automation to identify low-hanging fruit and manual testing to dive deeper and verify findings, ultimately delivering more value in a shorter amount of time. The rise of AI has introduced new possibilities for penetration testing, but it also presents challenges such as "hallucinations" and high costs, making human-in-the-loop approaches still vital. By finding the right balance between automation and manual testing, organizations can ensure comprehensive coverage and outpace attackers.