The chapter begins by highlighting the variety of health financing systems across the Caribbean, given the mixed history of the countries in the region. The context of the different systems is not as varied, since the countries face the same set of problems, with narrow-based economic systems and the need to deal with natural disasters fairly frequently. So, high out-of-pocket spending and fiscal space challenges stemming from the high-debt/low-growth profile of the countries emerge as major challenges for health financing. Confronting these challenges will require countries to take specific measures in crafting the health financing mechanism. Current health expenditure averaged 6.2% of gross domestic product across 13 Caribbean countries, in 2021, with the average expenditure per capita being US$ 767. Apart from making a strong case for additional government financing, the base of the financing system will have to be modified to ensure equity; a stronger noncommunicable disease morbidity focus within the system will be needed to ensure sustainability.