This chapter presents a brief history and analysis of the Caribbean Common Market (CARICOM)’s involvement in external trade agreements. Section two provides a concise description of the region and some basic trade data. Section three discusses CARICOM’s almost involuntary participation in non-reciprocal agreements such as the Caribbean Basin Initiative (CBI), the Caribbean-Canada Trade Agreement (CARIBCAN) and the Lomé Convention. It also focuses on more recent reciprocal agreements with the European Union (EU) and several Latin American countries. Section four assesses the impact of these agreements. It is argued that despite all the effort put into negotiating these various trade agreements, there is little evidence to suggest that the region has benefited directly through greater trade creation. However, a case can be made that, especially in the context of the Economic Partnership Agreement with the EU, that gains from development and technical assistance were important factors in these agreements. Section five concludes with a brief summary of the key issues.