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Dropping out of high school has long been associated with increased criminal behavior later in life. Whether this relationship is causal, however, is less clear. Utilizing propensity score techniques to more adequately address selection factors, we draw on data from the National Longitudinal Survey of Youth to test the degree to which dropout is causally related to criminal involvement across the transition to adulthood. Additionally, we incorporate theoretical developments from the education literature, examining the extent to which the association between dropping out and criminal involvement varies by whether a student was “pushed” or “pulled” out of school. Finally, we assess the degree to which continued disengagement with conventional institutions may be linked to route out of school and therefore may help to explain the relationship between dropout and subsequent criminal involvement. Our analysis reveals that dropout indeed appears to be causally related to criminal behavior, and that pathways out of school differentially affect both the crime-dropout link and patterns of involvement with conventional institutions. We suggest that the experiences of individuals who are pushed out of school largely drive the association seen between dropout and crime, and that being pushed out of school has long lasting implications across the life course.