Transgender women are disproportionately incarcerated across the United States, placing a burden of adverse health outcomes on this marginalized population. This exploratory study was designed to document the experiences of transgender women experiencing the cycle of incarceration; explore the degree to which the lack of targeted re-entry services contributes to this cycle of incarceration; and identify structural and/or community-level points for advocacy, support, and programming. We use qualitative interviews and geospatial mapping to describe the lack of access to resources, as well as challenges regarding finding housing, accessing health care, and meeting probation and parole requirements. In 2017, we interviewed six transgender women, all of whom are previously incarcerated adults residing in Allegheny County, Pennsylvania. Additionally, we mapped mental health providers and transinclusive resources using geographic information system software to explore barriers related to transportation and access. Results indicate that access to health care, housing, transportation, and transinclusive community support is the most significant barrier to successful re-entry. These analyses suggest that transgender women residing outside the central downtown area of Pittsburgh have increased difficulty regarding access to probation and parole offices, trans-inclusive health care, and LGBTQIA+ community spaces. These preliminary data suggest that there are missed opportunities within re-entry services to change the social and health trajectories of transgender women who are returning to their communities from jail or prison. Future multilevel interventions should incorporate health care, transinclusive community support, stable housing, and the alleviation of transportation barriers. Colocation of re-entry services may increase access, support, and treatment for transgender women re-entering the community.