The researchers of this collective case study sought to explore and understand the population of a cohort group of 22 pre-service teachers in agricultural education at the University of Illinois at Urbana-Champaign. The purpose of this study was to determine the outcomes of using problem-based learning cases by pre-service teachers to learn how to manage difficult student problems related to FFA supervision. Pre-service teachers faced difficulties in making decisions regarding ill-structured problems. They expressed challenges related to thinking of creative alternatives, considering the interests of others, and pursuing legal action if necessary in reaching solutions that were fair, relevant, appropriate, and effective. Ill-structured problems engaged pre-service teachers to be creative and reflective problem-solvers in making decisions. The pre-service teachers learned how to creatively generate alternatives, determine potential consequences for each alternative, consider possible implications of the consequences, and make decisions in a more reasonable period of time. Finally, pre-service teachers indicated that the ill-structured problems related to FFA supervision prepared them to solve similar problems that they may face as future agriculture teachers and exposed them to a variety of situations that they did not consider before the problem-based learning experience.