On August 27 and September 29, 2020, the CAC program, hosted full-day, virtual Tabletop Exercises (TTX) on maritime crime in the region. 65 prosecutors and law enforcement officers (police, Coast Guard, and Customs) from The Bahamas, Barbados, Dominica, Grenada, Guyana, Jamaica, St. Lucia, St. Kitts and Nevis, St. Vincent and the Grenadines, Suriname, and the Regional Security System (RSS) participated in the exercise. CBSI-Connect, the distance learning platform – supported by INL, facilitated the TTX which provided a venue for participants to network and an opportunity to practice spotting issues associated with interdiction, investigation, and prosecution. The participants deliberated on realistic maritime crime scenarios and examined important differences between states’ laws and operational gaps that can be exploited by transnational criminal organizations. The initiative also enabled participants to exchange views in a multi-agency setting to explore best practices; emerging trends resulting from COVID-19; shared challenges, and international instruments to address drugs, human, and weapons trafficking in the region. The exercises were led by a U.S.-based Maritime Law expert and aimed to facilitate community and future collaboration between professionals across countries and agencies. These events are the first of a two-part initiative to inform the Maritime Crime Assessment being conducted by CAC.