The purpose of this study is to develop a set of measures aimed at improving the efficiency of employment among graduates of secondary vocational education (SVE) institutions in the new regions of Russia, based on an analysis of their satisfaction with education, career plans, and identified employment barriers. The article presents the results of an assessment of employment success among graduates who obtained their SVE at the Federal State Budgetary Educational Institution of Higher Education Lugansk State Medical University named after Saint Luke of the Ministry of Health of Russia (LGMU named after Saint Luke). The survey covered graduates from various specialties of this institution, and data from guarantee letters reflecting employers’ intentions to hire were also analyzed. The scientific novelty of the study lies in the fact that, for the first time, key factors hindering the employment of SVE graduates in the healthcare system of the new regions of Russia were identified and ranked in the context of medical personnel availability. In addition, measures were developed and theoretically substantiated to provide comprehensive support to graduates from the completion of their studies to their adaptation in the healthcare workplace. These measures are integrated into a roadmap mechanism that incorporates the potential of guarantee letters as a tool for employment support. The study found that, overall, graduates are satisfied with the quality of education received and their practical training. However, the lack of sufficient hands-on experience, low salaries, and the high level of professional responsibility were cited by graduates as the main obstacles to employment. The analysis of guarantee letters revealed a significant imbalance in employment among graduates of specialties such as Prosthetic Dentistry and Pharmacy, indicating uneven demand for specialists and the need for a differentiated approach to both training and employment processes. Thus, the guarantee letter mechanism has proven to be effective; however, its further success requires a systematic approach implemented through the proposed roadmap . This roadmap integrates personalized monitoring and career guidance measures, coordination with employers, and support for graduate adaptation in the workplace. Overall, it represents a comprehensive solution that can help retain qualified personnel in the healthcare system of Russia’s new regions.