Debates on the reform of health care financing in the former socialist countries during the period of social transformation were conducted as part of a wider debate regarding changes in the overall social system. Existing financing models and innovative measures were reviewed. As part of such discussions, the voluntary health insurance market also received a lot of the attention. Different views were expressed in the debates that were conducted during the 1990s, from seeing a suitable supplementary source of health care funding to those who highlighted the constraints in its implementation and modest results that can be expected. As one of the criteria for assessing the suitability of this mechanism, we could review what has been achieved so far in its application. The paper looks at the ground covered and the situation in the former socialist countries at the end of the second decade of this century, with particular reference to Serbia and countries in its surroundings. When it comes to Serbia it can be expected that the limiting factors from the last ten years will be still manifested in the future. It is estimated that there are weak prospects of activating voluntary health insurance as a way to alleviate the problems of insufficient financing of the health care system.