This paper presents findings from a feminist pathways study undertaken with imprisoned Tomboys, a gender sexual minority group in Thailand. Utilizing life-history interviews, we mapped Tomboys’ journeys into prison. Results showed two pathways. The first, insubordinate lifestyles, was characterized by substance abuse and life-long lawbreaking. The second pathway - support, sacrifice, suffering - was marked by romantic love and familial caregiving. Many of the experiences and central mechanisms that constituted both trajectories aligned with those found in previous feminist pathways and queer criminological scholarship. Nevertheless, qualities distinct to Tomboys’ incarceration journeys were also identified.