A large body of work has examined factors that push and pull youth to drop out. However, a relatively minimal amount of work has examined whether and how these factors cluster in individuals' lives preceding or concurrent to leaving school. This study used Latent Class Analysis with a national sample (N = 1,942) to examine how push, pull, and protective experiences clustered in the lives of individuals who left high school without graduating. Then, we asked how the resultant classes differentially predicted youth re-engagement in educational endeavors. We identified three classes: youth with the presence of protective factors and absence of push/pull factors (Quiet Dropouts), youth with the presence of protective factors and an abundance of push/pull factors (High Adversity), and youth with the presence of instability in factors related to social relationships and school or housing (Instability). Results indicated each profile differentially predicted youths' re-engagement in education and achievement of educational outcomes.