This study involved an examination of sex-based differences in judicial decision making during pretrial, an understudied stage of the criminal court process. We also examined whether defendants’ sex interacted with other legal and extralegal case characteristics, or the context of the county in which defendants were processed. Analyses of data collected from 62 large urban counties for the years 1994 through 2006 revealed that overall, women were treated more leniently than men throughout the pretrial process. Results also indicated that defendants’ sex interacted with other case characteristics to influence pretrial decisions and outcomes, and that judicial decisions were shaped by the sociopolitical context of the county in which these defendants were processed.