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What factors influence prosecutors’ decisions about whether to request bail, and judges’ decisions about whether to set bail? This presentation discusses a unique research project in which thousands of arraignments in four boroughs of NYC were observed during 2018. Results illustrate how prosecutors’ bail (or release) requests differ by various features of the case or defendant. The relationship between a prosecutor’s request and the actual arraignment outcome is also explored, offering further insight into the influence of the prosecutor during the pretrial phase of the criminal justice process. The effect of a defendant’s behavior during arraignment is also examined, revealing the importance of considering contextual and situational factors. Ultimately, this project demonstrates the unique insights that observational data can provide about pretrial release decisions – insights that can inform broader discussions about bail reform.