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This chapter describes transwomen’s experiences in diverse arenas of the criminal justice system, including law enforcement and corrections. Specifically, it describes transwomen’s encounters with police officers and their mistreatment while in custody. Criminalization, police violence, and micro-aggressions are discussed as strategies for enforcing gender conformity. This chapter highlights the unique social and health care needs of transwomen and their vulnerability to harassment, hate crimes, intimate partner violence, and police profiling in the community. It also discusses recent legal decisions and implications for gender-affirming treatment in detention facilities. Lastly, the chapter provides recommendations for increasing awareness of transwomen’s issues and for promoting gender-affirming practices in diverse arenas of the criminal justice system.