As part of a larger project focused on the intersection of educational and health trajectories over the life course, we use in-depth interviews with 28 adults who experienced multiple non-promotional school changes during the course of their K-12 schooling in three U.S. urban centers to advance understanding of frequent student mobility. Prior research focuses predominantly on isolating the impact of student mobility while saying little about processes through which mobility influences educational trajectories in particular contexts. Frequent student mobility was intertwined with adverse childhood experiences and access to coping resources, and these forces shaped participants’ trajectories in patterned ways. Supporting frequently mobile students, almost a third of school-age children in the United States, will require greater attention to the reasons for, processes of, and contexts of student mobility.