This chapter traces Zimbabwe’s protracted quest to establish a national health insurance (NHI) scheme as part of its commitment to Universal Health Coverage by 2030. Despite over two decades of policy debate, the scheme remains unrealized, leaving nearly 90% of the population—particularly rural communities, the poor, and those in the informal sector exposed to health risks—without health insurance. In 2024, the Ministry of Health and Child Care reopened consultations with stakeholders in an effort to revive the stalled initiative. Using a desk-based review of primary and gray literature, the chapter interrogates the institutional framework, political economy, and the evolving macroeconomic environment that have constrained implementation. Meanwhile, the World Health Organization highlights how poorer households and those with older members, excluded from market-based health insurance, face financial hardship from out-of-pocket health expenses. The findings point out that successful implementation of an NHI in Zimbabwe requires innovative, context-specific funding models that address Zimbabwe’s fragmented health system, large informal sector, and persistent economic instability. It concludes by underscoring the urgency of institutional reform, inclusive stakeholder engagement, and sustainable financing frameworks to ensure universal, affordable health protection for all Zimbabweans.