This paper explores the pitfalls, successes, and challenges of the Technical Vocational Education and Training (TVET) intervention, which was anchored by a robust framework outlined in the 1990 CARICOM Regional Strategy for TVET document. Specifically, the paper examines the three critical sections of the CARICOM document to show the achievements of TVET, or lack thereof, since the implementation of the Regional Strategy for TVET.