Despite the increasing body of procedural justice research studying individuals involved in the criminal justice system, this strand of literature has used different approaches to measure procedural justice and legitimacy. The present study assesses the different theoretical assumptions of these approaches across two criminal justice settings, namely, policing and courts. In addition, we examine how procedural justice stemming from interactions with police officers and judges is related to legitimacy and reoffending behavior postrelease. Using data on adult detainees who entered Dutch pretrial detention centers, our findings support the theoretical assumptions regarding procedural justice and felt obligation to obey the law in both criminal justice settings. Furthermore, path analyses show that perceptions of procedural justice arising from encounters with police officers and judges are related to a higher sense of obligation to obey the law, which in turn is associated with a lower risk of reoffending.