Educators have long asserted that the middle grade years (typically, grades six through eight) are a time of both great importance and vulnerability in students' K-12 schooling. Anecdotal and empirical evidence suggest that students encounter new social and emotional challenges, increased academic demands, and major developmental transitions during the middle grade years. In this study, we investigate whether and how students' achievement and attendance change between grade four and eight and identified moments during this period when students' achievement and attendance suggest that they will struggle to graduate from high school within four years.