Background: One of the most controversial issues in restructuring the Polish health insurance system is the implementation of private voluntary insurance and creation within it a new insurance product known as occupational health services (OHS). In this article some opportunities and dilemmas likely to be faced by providers and employers/employees, when contracting with insurance institutions, are considered as a contribution to the discussion on private insurance in Poland. The basic question is how private insurance institutions could influence the promotion of different preventive activities at the company level by motivating both OHS providers and employers. Material and Methods: The descriptive qualitative method has been applied in the analysis of legal acts, scientific publications selected according to keywords (Pubmed), documents and expert evaluations and research project results. Results: Taking into account the experiences of European countries, described in publications, international experts' opinions and results of research projects the solution proposed in Poland could be possible under the following several prerequisites: inclusion of a full scope of occupational health services into the insurance product, constant supervision of occupational medicine professionals, monitoring of the health care quality and the relations between private insurers and OHS provider and implementation of the economic incentives scheme to ensure an adequate position of OHS providers on the market. Conclusions: The proposed reconstruction of the health insurance system, comprising undoubtedly positive elements, may entail some threats in the area of health, organization and economy. Private voluntary health insurance implementation requires precisely defined solutions concerning the scope of insurance product, motivation scheme and information system. Med Pr 2014;65(2):279–287