Over the past two decades, the growing number of women entering the police profession has challenged the historic male dominance of the occupation. Research from the United States and the United Kingdom has examined whether men and women police differ in their assessments of working conditions, occupational opportunities, and other aspects of police work. However, to date, no attempt has been made to conduct a quantitative study of gender across sociopolitical contexts or to assess the applicability of models constructed in those two countries to Caribbean nations. This study employed survey data from a sample of police constables and their immediate supervisors in three Caribbean nations. The survey included 1,237 constables and supervisors. Eleven percent of the respondents were women. Constables were asked about various aspects of policing, working conditions, and the nature of their duties. The questions were based on 24 theories evaluated in U.S. and United Kingdom literatures. Few differences between genders emerged from comparisons within nations, although differences have been documented in the U.S. and the United Kingdom. The findings suggest that gender models used in developed nations do not necessarily explain differences in developing nations. In addition, the findings suggest that future studies on the policing experience should pay attention to more macro-level factors specific to each nations’ police organization and administration. Notes, references