In this presentation, Jesse Roberts will offer a thorough exploration of the diverse methodologies and approaches in the world of penetration testing. From white-box to black-box, external to internal, and automated versus manual tests, this presentation delineates the unique objectives, benefits, and scenarios where each form is most applicable. With a focus on real-world application, attendees will learn about the strategic nuances of each approach, ensuring they can effectively assess and bolster their organization's cybersecurity defenses. This comprehensive overview is designed to empower participants with the knowledge to select and implement the most suitable penetration testing methods for their specific needs and environments.