Starting in 2020, the insurance market in Russia has faced a number of challenges, which are significantly reflected in the development strategies of insurance companies and the sets of products they offer. As a result of several successive crises, such as the COVID-19 pandemic and the post-2022 crisis, insurers’ approach to Voluntary Medical Insurance (VMI) and Drug Insurance (DI) programs has changed significantly. The purpose of the study is to measure the flexibility of VMI and DI products in the Russian Federation and assess their content content. The article presents the results of a study of VMI and programs offered by the largest Russian insurance companies, which together receive almost 80% of all insurance premiums. The content analysis of the programs offered by insurers allowed us to assess not only the prevalence of the studied segments among insurers, but also the fullness and diversity of insurance programs. A system for evaluating VMI, DI, Telemedicine products, as well as new products such as assay insurance is proposed. Indexes have been formed that make it possible to conduct a comparative analysis of insurance programs and provide a situational assessment of the state of these segments in the Russian Federation (RF) in 2025. The results of the study provide insurance companies with a comparative description of insurance products, which can optimize the set of programs, expand the product line, update the services offered and improve customer interaction. Using the research data, clients can choose the company and program that best meets their requirements and needs. In addition, these studies can be used to modernize and update government regulatory and incentive programs for the development of insurance business in Russia in the VMI and DI segments, as well as to further improve scientifically sound methodological solutions in the field under study.