Contributing to the ongoing debate about policy feedback in comparative public policy research, this article examines the evolution of healthcare financing policy in Ghana. More specifically, this article investigates the shift in healthcare financing from full cost recovery, known as ‘cash-and-carry’, to a nation-wide public health insurance policy called the National Health Insurance Scheme (NHIS). It argues that unintended, self-undermining feedback effects from the existing health policy constrained the menu of options available to reformers, while simultaneously opening a window of opportunity for transformative policy change. The study advances the current public policy scholarship by showing how the interaction between policy feedbacks and other factors—particularly ideas and electoral pressures—can bring about path-departing policy change. Given the dearth of scholarship on self-undermining policy feedback effects in the Global South, this contribution’s originality lies in its application of the novel theory to the sub-Saharan African context.