Fire-dependent pine forests in the Caribbean Basin cover extensive areas in the coastal plain of the Caribbean Sea and Gulf of Mexico and on several islands in the Bahamas Archipelago, Cuba, Hispaniola, and the Honduran Bay islands. These forests are high in conservation value but, unfortunately, remain mostly unprotected. Moreover, even though they are fire dependent, the use of fire for forest management often suffers from poor public perception and is prohibited by law in several countries. In this paper, we describe the fundamental links among fire, forest regeneration, and forest persistence in these ecosystems. We identify two general strategies based on the presence or absence of pine seedling adaptations for fire survival and describe management implications of these two strategies. We also introduce conceptual models describing fire, forest structure, and regeneration strategy linkages.