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Policing is considered highly stressful, and this is particularly true for the police in Jamaica. Along with the everyday demands and pressures of police work, these officers also contend with socio-economic challenges and high levels of crime and violence. However, there is a lack of empircal data on police stress and its effects in this context. Furthermore, while much progress has been made over the past four decades, it has been argued that there is a need for more thorough and organised research frameworks in understanding the complexities of police stress and its consequences. The current research was consistent with this recommendation and sought to provide a comprehensive study of work-related stress in the Jamaican Police Force. The first objective was to identify sources of occupational stress among police officers. The second was to use a multidimensional approach, guided by a contemporary theoretical framework, to examine the determinants of police officers’ well-being. This research investigated the relative contribution of occupational factors, individual differences, and work-family conflict in predicting occupational and personal well-being outcomes. Moderation effects of positive work factors and coping, as well as the intermediate role of subjective appraisals in the stress-strain relationship were also examined. Findings showed that organizational stressors, including inadequate pay and resources, poor working conditions, and poor management practices were the primary sources of stress for the Jamaican police. Confrontations with harm or death, public scrutiny and criticism as well as stress from the interplay of work and family life were also important.