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This chapter will examine trends in human trafficking in Caribbean and African islands over the past five years as documented in the US Department of State’s annual Trafficking in Persons Report (2016–2021). The countries that will be examined include Antigua and Barbuda, Bahamas, Barbados, Cuba, Dominican Republic, Haiti, St. Lucia, St. Vincent, and the Grenadines in the Caribbean region and Cabo Verde, Comoros, Madagascar, Mauritius, Seychelles, Zanzibar, Tunisia, and Bijagos, Guinea-Bissau, in Africa. This article will examine what countries in these two regions have accomplished in the areas of prosecution of traffickers, victim protection, and prevention activities, as well as discuss the challenges and shortcomings in the anti-trafficking efforts of these island countries. The chapter will discuss the common elements across these regions facilitating success and failures in combating human trafficking. The chapter will end by discussing what policy recommendations, capacity-building initiatives, and cross-regional collaborations could be launched to address these collective trafficking problems.