The Caribbean states have recognised the necessity of collaboration to mitigate their security vulnerabilities. The region faces a range of security threats, including, but not limited to, drugs and human trafficking. Within The Caribbean Community, there are two primary security governance entities, CARICOM IMPACS and the Regional Security System (RSS). The region has also been influenced by the United States through the Caribbean Basin Security Initiative (CBSI). Despite these security governance structures, the region continues to grapple with addressing security threats, prompting ongoing debates about factors hindering and enabling the collaborative efforts by member states. Eleven (11) interviews with active and retired officers at the rank of major or higher from five (5 countries) and two regional (2) organizations were conducted. MaxQDA was used to analyze the data thematically. Eight (8) enabling and eight (8) hindering factors were identified. The manuscript aims to address the challenges and promote factors that can strengthen future collaboration among the Caribbean countries.