This article addresses the question of policy circumvention in federal courts by examining how legal actors have differentially adapted their adjudicatory practices after U.S. v. Booker (2005) rendered the federal sentencing guidelines advisory rather than mandatory. By linking two distinct bodies of scholarship—the courts-as-communities scholarship that assesses and explains locale-based variations in criminal court operations and the socio-legal “law and organizations” scholarship that addresses how organizational actors translate and implement top-down legal policy reforms—this article argues that law-as-practiced is always temporally and spatially contingent. Expanding on prior quantitative research that addresses district-specific adaptations to Booker, this article reports on findings from a qualitative study recently conducted by the author of four federal districts. Based on these findings, this article examines within-district changes and between-district variations in: (1) legal actors’ perceptions of whether the Booker policy change impacted local practices and outcomes, and if so, the extent of its impact; (2) how legal strategies and practices have changed at three stages of the criminal process: charging, pre-conviction plea negotiations, and formal sentencing; and (3) interviewees’ perceptions about whetherBooker contributed to greater racial or other disparities in case outcomes. Findings indicate that a dynamic, proactive adaptation process is taking place, conditioned by local norms but not fully dictated by those norms. They also make clear that changes in sentencing outcomes in the post-Booker period are not simply the result of liberated judges exercising their discretion, but rather are jointly produced by courtroom workgroup members through both contestation and cooperation. This inquiry is especially timely given both ongoing and proposed changes in federal sentencing policy that aim to maintain severity in punishment, re-impose constraints on legal actors, and threaten to exacerbate racial and ethnic inequalities in the federal criminal system.