Penetration testing is a key practice toward engineering secure software. Malicious actors have many tactics at their disposal, and software engineers need to know what tactics attackers will prioritize in the first few hours of an attack. Projects like MITRE ATT&CK™ provide knowledge, but how do people actually deploy this knowledge in real situations? A penetration testing competition provides a realistic, controlled environment with which to measure and compare the efficacy of attackers. In this work, we examine the details of vulnerability discovery and attacker behavior with the goal of improving existing vulnerability assessment processes using data from the 2019 Collegiate Penetration Testing Competition (CPTC). We constructed 98 timelines of vulnerability discovery and exploits for 37 unique vulnerabilities discovered by 10 teams of penetration testers. We grouped related vulnerabilities together by mapping to Common Weakness Enumerations and MITRE ATT&CK™. We found that (1) vulnerabilities related to improper resource control (e.g., session fixation) are discovered faster and more often, as well as exploited faster, than vulnerabilities related to improper access control (e.g., weak password requirements), (2) there is a clear process followed by penetration testers of discovery/collection to lateral movement/pre-attack. Our methodology facilitates quicker analysis of vulnerabilities in future CPTC events.