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The criminal justice system, a site of historical tension and distrust for the transgender community, provides an important context in which to explore the workplace experiences of transgender employees. Researchers have begun to systematically document some of those experiences, highlighting disproportionate trends in mistreatment, abuse, and discrimination. This study presents an exploratory examination of how law enforcement and corrections agencies have facilitated and prevented inclusion of this group within their ranks. Surveys and interviews were conducted with transgender personnel in this field to gain an understanding of these experiences. Findings demonstrate how inclusion and exclusion are manifested across both informal and formal mechanisms. Consistent with prior research, transgender personnel experience inclusion through supportive leadership, adopted and enforced policies, and an agency focus on maintaining professional standards and values. They also experience exclusion in the form of unaddressed harassment, social isolation, barriers in hiring and promotion, job restrictions, and job loss. These exclusions are amplified in organizational cultures structured heavily around heteronormative masculinity, an “us versus them” mentality, and reactive, rather than proactive, strategies. Thus, preventing exclusionary practices for this group necessarily includes attentiveness to existing culture in addition to revising policies and practices around workplace inclusion.