This article examines gendered profiles of crime and punishment in Barbados between 1878 and 1928. During this period, Barbados stood out from the rest of the Caribbean in levels of imprisonment of women. The context of unusually high levels of female committals to custody – related to (1) women’s prominence in the labor force, (2) entrapment within conditions of near-total plantation monopoly, (3) high levels of male migration and (most importantly) criminalization of so-called “abandoned” dependants – provides the backdrop for an examination of penal regimes in Barbados. Using spatial frames, particularly those generated in studies of “colonial geographies,” the article surveys gender differences in crimes, institutional arrangements, and punishments within prison. It also analyzes penal system changes that occurred over the period, signaling the transition to a new disciplinary regime.