Preservice teachers are typically educated in university settings and learn teaching methodology through coursework. Many preservice teachers find themselves underprepared for handling challenging situations in art classrooms. Teaching is very often influenced by contextual factors such as the space and design of the classroom, demographics and socioeconomics of the students, school culture, parental expectations, administrative support and policies, as well as state and district standards. This article explores the strategy developed by two art education professors called The Worst Case Scenario Art Game (WCSAG). The game is designed to help preservice teachers have exposure to complex teaching situations and learn to problem solve accordingly. This article describes the WCSAG and how preservice teachers learned from the experiential assignment.