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Existing research on criminal courts tends to focus on the discretion of judges and prosecutors separately or group these two legal actors together, failing to clarify the distinct role of each and the interplay of discretionary decisions. Instead, as Jeffrey Ulmer suggests, “We should study the interactions that jointly produce discretionary decisions” (Ulmer 2019, p. 483). Drawing on twelve months of ethnographic fieldwork in two mid-sized midwestern District Attorney’s offices, this paper explores the interplay between judicial and prosecutorial discretion. I find that prosecutors learn the specific tendencies of different judges and based on this knowledge, use various techniques to constrain judicial discretion. For example, they may resolve a case with a mandatory minimum charge if they believe a judge would be too lenient and not follow their prison recommendation. On the other hand, they may choose to resolve a case with a charge that has a low maximum sentence if they believe the judge would be too harsh and want to limit the possible prison term for a defendant. These findings highlight how prosecutors can use their discretion to constrain the discretion of judges and how the techniques they use vary depending on their perceptions of the judge’s tendencies.