The forest transition model posits that as a society advances to later stages of demographic and economic transitions, reforestation begins to outpace deforestation. However, this concept was constructed on endogenous factors within more developed nation-states, giving scant attention to exogenous factors that today's globalising world has made increasingly relevant. Further, the transition period between net deforestation and net reforestation needs to be better understood, particularly in developing countries that may be going through a forest transition. Here we address these issues in the Cockpit Country region of Jamaica through a remote-sensing analysis of forest-cover change from 1987 to 2011. Our findings suggest this region is in the turnaround period of the forest transition attributable to changes in demographics and the Jamaican agricultural sector, which has been decimated by neoliberal economic policies leading to agricultural land abandonment. This study contributes to the development of the forest transition concept through adding a Caribbean case study inclusive of exogenous factors related to the changing global political economy and addressing the mechanisms at work during the forest transition turnaround.