Few researchers have concerned themselves with qualitative gender-comparative studies of women’s and men’s prison trajectories – particularly appraisals relating to international cross border drug trafficking (ICBDT). Using life history interviews with prisoners incarcerated in three regions of Thailand, we describe, examine and compare the features of women’s and men’s pathways to prison for ICBDT. Overall, the findings point to both similarities and divergences in experiences by gender. Three pathways to prison emerged for both women and men: (1) ‘deviant’ lifestyle, (2) economic familial provisioning and (3) inexperience and deception. However, gendered variance was found within these pathways; an additional woman-only trajectory, the romantic susceptibility pathway, was also identified.