The continued preponderance of large health budget deficits in low-income countries has led to increasing international debate over the role that private health insurance could play in providing additional financing for health. However, the market failures inherent to insurance constitute a major concern and proponents are now advocating that states employ calculated regulations to offset these tendencies. This article uses an examination of the policy evolution of the Government of Uganda to demonstrate how one low-income country has heeded the call for regulation yet, so far, has remained unable to implement the resulting policies. In doing so, the case study exposes the contradiction underlying the impetus for the state to regulate private health insurance in low-income settings, namely, that while private health insurance is advanced as one response to the failure of the nation state and its inability to provide adequate health services for its population, the same 'failing' state is now being called upon to govern against the market failures inherent to the product.