Crime in the Caribbean consists of drug and human trafficking, weapons smuggling and terrorism, and is fuelled by this region’s physical location as a gateway to the United States (US). Significant challenges to effective policing are transnational (TN), making the region an ideal testing ground to study transnational police cooperation (TNPC). Current cooperation is seen as reactive and hindered by the Caribbean’s topography, cultures, legal systems, nepotism and territorialism. Using a phenomenological perspective, this qualitative study investigates TNPC in the Caribbean region, focusing on Puerto Rico (PR) and the Dominican Republic (DR), assessing how TNPC works within this region, current structures and operations in the Caribbean. Other researchers such as Malcolm Anderson and Ethan Nadelmann have established the theoretical research base upon which this study is built. However, as empirical research is limited around this particular study, this paper primarily draws upon interviews with law enforcement agents in PR working for the High Intensity Drug Trafficking Area (HIDTA) Program, administered by the White House Office of National Drug Control Policy. This study investigates stakeholders’ perspectives and the various methods of TNPC with the aim of improving the efficiency and effectiveness of multi-agencies towards a practical model, as embodied by HIDTA. This research is the first of its kind, offering a new direction for theory and research.