Learning Assistants (LAs) help students develop a deeper understanding of content and are particularly effective during active learning instruction. A foundational pillar of the LA model is the LA pedagogy course, which teaches LAs about evidence-based instruction and about how students learn (Otero et al., 2010). From LA survey responses, this study identifies interactions between LAs and students that have the potential to negatively impact the classroom environment and how other students learn—what we call “challenging interactions.” Challenging interaction training was developed for LAs taking the pedagogy course by using scenarios that LAs can act out and reflect on in class. This training aims to guide LAs as they develop their own strategies for how to properly navigate these interactions. Because of the potential negative impacts of these interactions, training LAs to address and manage these situations is important. If LAs can properly navigate these challenging interactions, they will be better able to facilitate deeper learning in their respective LA-supported classrooms.