Health reform is inherently political. Sound technical analysis is never enough to guarantee the adoption of policy. Financing reforms aimed at promoting equity are especially likely to challenge vested interests and produce opposition. This article reviews the Health Insurance policy development in South Africa between 1994 and 1999. Despite more than 10 years of debate, analysis and design, no set of social health insurance (SHI) proposals had, by 1999, secured adequate support to become the basis for an implementation plan. In contrast, proposals to re-regulate the health insurance industry were speedily developed and implemented at the end of this period. The processes of actor engagement and management, set against policy goals and design details, were central to this experience. Adopting a grounded approach to analysis of primary interview data and a range of documentary material, this paper explores the dynamics between reform drivers engaged in directing policy change and a range of other actors. It describes the processes by which actors were drawn into health insurance policy development, the details of their engagement with each other, and it identifies where deliberate strategies of actor management were attempted and the results for the reform process. The primary drivers of this process were the Minister of Health and the unit responsible for health financing and economics in the national Department of Health Directorate of Health Financing and Economics, with support from members of the South African academic community. These actors worked within and through a series of four ad hoc policy advisory committees which were the main fora for health insurance policy development and the regulation of private health insurance. The different experiences in each committee are reviewed and contrasted through the lens of actor management. Differences between these drivers and opposition from other actors ultimately derailed efforts to establish adequate support for any form of SHI, even as regulatory proposals received sufficient support to be enacted in legislation. Drawing on this South African experience together with a simple analytical framework, the authors highlight five potential strategies by which reform drivers of any policy process could create alliances of support sufficient to overcome potential opposition to proposed policy changes. As little is currently known on how to manage the process of engaging actors in reform processes, these findings provide a foundation for further analysis of this issue.