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Caribbean prisons face a myriad of challenges, including a high percentage of individuals held in prison for prolonged periods of pretrial incarceration. Close to forty five percent of the prison population in Caribbean countries is made up of pretrial detainees not yet convicted of a crime. Despite its high presence in the criminal justice system, research related to pretrial population, pretrial processes and judicial decision making at this stage is often overlooked in Caribbean criminological research. This study examines legal and extra-legal factors that impact pretrial decisions (i.e., granting or denying bail) and the consequences that these decisions have on subsequent stages of the judicial process in terms of guilty pleas and sentence length. Logistic and negative binomial regressions indicate that both legal and extralegal variables influence the decision to grant bail, and that detainees who spend longer in pretrial detention are less likely to plead guilty and more likely to serve longer sentences. These findings shed light on the dynamics of pretrial justice in Caribbean contexts.