Research investigating how trans women come to be criminalized is limited. In this article, using a feminist pathways approach, we explore phu-ying-kham-phet (Thai trans women’s) narratives of their journeys to prison. Results show several common threads of discrimination, oppression, marginalization, and harm in their backstories. These encompassed adverse childhood experiences, such as abuse, familial disavowal of feminine gender expression, separation from parents, and impoverishment. During adulthood, discrimination in the labor market was common, as was substance dependence, earning a living in the underground economy, criminal (in)justice system mistreatment, and, for some, domestic violence victimization. In addition to identifying common features in the life histories of imprisoned phu-ying-kham-phet, we mapped the circumstances, experiences, and events that culminated in their imprisonment. Three distinct pathways to prison were found: 1) criminalized lives, 2) normative lives, and 3) other. Many of the central mechanisms constituting these trajectories aligned with previous cisgender feminist pathways studies. However, features unique to the imprisonment journeys of phu-ying-kham-phet were also identified.