Transgender women experience high rates of police contact, arrest, and incarceration, yet little attention has been paid to the specific life experiences and circumstances leading up to arrest for transgender women. This study conducted in-depth interviews with 21 transgender women living in Chicago using a life timeline method to examine pathways that lead to or prevent transgender women from entering the criminal legal system. Findings indicate that transgender women’s pathways mirror those experienced by cisgender women but are distinctly contoured by anti-transgender discrimination and marginalization. Participants also identified forms of resilience and protective factors against police contact and arrest.