Youth with poor self-regulation or criminal attitudes are at risk for recidivism. Researchers have yet to examine how self-regulation and criminal attitudes intermix to influence recidivism. The present study employed a large sample of 26,947 youth in the Florida Juvenile Justice System to examine the effect of criminal attitudes on the association between self-regulation and recidivism over a 1-year period. The results indicated that the influence of self-regulation on recidivism varied based on youths’ attitudes. Although self-regulation affected recidivism among youth with average (dy/dx = –.03, SE = .01, p < .001) and less criminal (dy/dx = –.05, SE = .01, p < .001) attitudes, self-regulation was not associated with recidivism among youth with more criminal attitudes (dy/dx = –.01, SE = .01, p = .150). These findings demonstrate mechanisms that may promote sustained justice system involvement and identify key levers for reducing youth recidivism.