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Cyberattacks are a major threat in the modern era, yet there is a lack of information on how cybercrime groups think and operate. This paper aims to better understand cyber adversaries by analyzing penetration testing teams during the 2018 and 2019 National Collegiate Penetration Testing Competition, in which groups of students performed similar actions as cybercriminals, attempting to identify and exploit system vulnerabilities. Using penetration testing teams as an ethical proxy for cybercrime groups allows the researchers to study group dynamics as well as factors impacting the rationality of cybercriminals. Themes identified in manually coded interview transcripts are compared to the existing literature on cybercrime groups. Similar to what is established in the prior research, themes emerged in the interviews on the group structure and dynamics of each team, featuring elements of leadership, division of labor, the role of each team member, the presence of partners and subgroups, communication within the team, and interpersonal team member relationships. Other apparent factors that specifically impacted the bounded, or limited, rationality of the team members included setbacks and problem solving, the competition environment, stress, and issues with morale. This comparison of penetration testing groups with cybercrime groups allows for the development of a better understanding of the operations and rational thinking of a criminal organization, which may lead to a better understanding of how to prevent or defend against cyberattacks, such as by improving response times of the security team or by increasing the difficulty of penetrating the technical environment