Over the past two decades, Trinidad and Tobago has promoted explosive expansion of tertiary education. As with many growing postsecondary education systems, this increase in tertiary enrollment has led to the development of student support services (Haddad & Altbach, 2009). The field of student services is growing throughout the Caribbean (Reynolds, 2008), but there is currently little research on the role of student services in fostering students' sense of belonging specific to the Caribbean cultural context. Using data from over 900 students at the University of Trinidad and Tobago, we examined students' sense of belonging in the context of T&T. Findings point to the key role that student services professionals play in promoting students' sense of belonging, but the limited interactions that students are having with student services staff and key differences by students' race, religion, program level, and major should be noted. We also identified the indirect role of cocurricular engagement in promoting sense of belonging and the main barriers that prevent students from participating in more cocurricular activities. These findings have important implications for the work of student services professionals in T&T and also expand our understanding of constructs, such as student engagement and sense of belonging, ideas that have been well-researched in the US to a very different tertiary education system.