One of the earliest studies that focused on functioning in the Caribbean people was recorded in Edith Clarke’s book first published in 1957. This study used direct and participant observations in multiple Jamaican communities. Although this and earlier studies did not use standard psychological testing, they were among some of the first efforts to use systematic methods to observe functioning in Caribbean people. Since the mid-twentieth century, multiple studies conducted in the region have used tests and measures designed by researchers of European heritage for people of similar backgrounds who reside primarily from North America and Europe. Equally important is that such assessment tools are used in clinical as well as industrial and organizational contexts. While these tools have provided important information on Caribbean people’s functioning, their lack of attention to reliability and validity concerns for the Caribbean populations have made their findings somewhat questionable. This chapter addresses the historical use of psychological assessment in practice and research throughout the Caribbean region. Although to a lesser extent, it also focuses on contemporary use of psychological assessment tools in the Caribbean context.