Cybersecurity competitions are an effective and engaging way of providing students with hands-on experience of real-world security practices. Unfortunately, existing competitions are ill-suited in giving students experience in penetration testing, because they tend to lack three key aspects: (1) pivoting across multiple machines, (2) developing or implanting custom software, and (3) giving students enough time to prepare for a lively in-class competition. In this paper, we present the design, implementation, and initial run of King of the Hill (KotH), an active learning cybersecurity competition designed to give students experience performing and defending against penetration testing. KotH competitions involve a sophisticated network topology that students must pivot through in order to reach high-value targets. When teams take control of a machine, they also take on the responsibility of running its critical services and defending it against other teams. Our preliminary results indicate that KotH gives students valuable and effective first-hand experience with problems that professional penetration testers and network administrators face in real environments.