Background: In early 1990s, Tanzania like other African countries, adopted health sector reform (HSR). The most strongly held centralisation system that informed the nature of services provision including health was, thus, disintegrated giving rise to decentralisation system. It was within the realm of HSR process, user fees were introduced in the health sector. Along with user fees, various types of health insurances, including the Community Health Fund (CHF), were introduced. While the country’s level of enrollment in the CHF is low, there are marked variations among districts. This paper highlights the role of decentralised health management and leadership practices in the uptake of the CHF in Tanzania. Methods: A comparative exploratory case study of high and low performing districts was carried out. In-depth interviews were conducted with the members of the Council Health Service Board (CHSB), Council Health Management Team (CHMT), Health Facility Committees (HFCs), in-charges of health facilities, healthcare providers, and Community Development Officers (CDOs). Minutes of the meetings of the committees and district annual health plans and district annual implementation reports were also used to verify and triangulate the data. Thematic analysis was adopted to analyze the collected data. We employed both inductive and deductive (mixed coding) to arrive to the themes. Results: There were no differences in the level of education and experience of the district health managers in the two study districts. Almost all district health managers responsible for the management of the CHF had attended some training on management and leadership. However, there were variations in the personal initiatives of the top-district health leaders, particularly the district health managers, the council health services board and local government officials. Similarly, there were differences in the supervision mechanisms, and incentives available for the health providers, HFCs and board members in the two study districts. Conclusion: This paper adds to the stock of knowledge on CHFs functioning in Tanzania. By comparing the best practices with the worst practices, the paper contributes valuable insights on how CHF can be scaled up and maintained. The study clearly indicates that the performance of the community-based health financing largely depends on the personal initiatives of the top-district health leaders, particularly the district health managers and local government officials. This implies that the regional health management team (RHMT) and the Ministry of Health and Social Welfare (MoHSW) should strengthen supportive supervision mechanisms to the district health managers and health facilities. More important, there is need for the MoHSW to provide opportunities for the well performing districts to share good practices to other districts in order to increase uptake of the community-based health insurance.