In feminist criminology, there is a growing body of research exploring pathways to prison, but few studies have specifically sought to map women’s journeys into the criminal justice system for crimes of physical violence and sex offending. Gender comparative research is sparse, and, to date, we know little about women and men imprisoned in Thailand for these types of crimes. Subsequently, in this paper, we report findings from a gender comparative feminist pathways study conducted in Thailand, with a specific focus on violence and sex offending; namely, homicide, sexual assault, human trafficking, and sex work-related offences. We utilise a qualitative analysis of life-history interviews to centre and value these women’s and men’s voices, establish their backstories, and thematically map their imprisonment trajectories. Three pathways to prison emerged: (1) lifestyles of contravention, (2) harmed and harming, and (3) destructive masculinity. Utilising the participants’ descriptions, we highlight similarities and variance by gender within and between these pathways.