Engagement, dropout, and reengagement within the school year are explored using records and survey data for students in grades seven through twelve. Reengagement is defined as returning to school after an episode of dropout and remaining continuously enrolled until the end of the school year. An episode of dropout is considered to be 20 consecutive unexcused absences. The inquiry explored factors that differentiate students who reengage from end-of-year dropouts or students who never return to school. Using both descriptive and predictive analyses, three key findings emerged. First, students who reengage after an episode of dropout have higher proportions of behavioral incidents, enrollment in low-track coursework, being overage for grade and the lack of course failure. Second, the only school-level predictor of significance in predicting reengagement is the school performance rating. Third, the results from this research are not consistent with existing literature about between-years students who reengage two to twelve years after dropping out. This research details the challenges of using with-year data, drawbacks of using advanced modeling techniques with limited data, and potential misuses of early warning systems. The research was exploratory and as such has substantial limitations including extensive missing data and measurement concerns with the student survey. In spite of the challenges, limitations and weak predictive models, continued research is recommended in this area because little research is available about what factors predict student reengagement with school. More research is needed to understand reengagement with school in order to close resistant racial and socioeconomic achievement gaps