Transitions from middle school to high school mathematics programs can be problematic for students due to potential differences between instructional approaches and curriculum materials. Given the minimal research on how students experience such differences, we report on the experiences of two students as they moved out of an integrated, problem-based mathematics program in their middle school into a high school mathematics program that emphasized procedural fluency. We conducted an average of two interviews per year for two and a half years with participants and engaged in participant-observation at their high school. In this study, we illustrate an analytic process for detecting discontinuities between settings from participants' perspectives. We determined that students experienced a discontinuity if they reported meaningful differences between settings (frequent mention, in detail, with emphasis terms) and concurrently reported a change in attitude. Additionally, these students' experiences illustrate two opportunities to learn during boundary-crossing experiences: identification and reflection. (Contains 5 footnotes.)