The objective of the study was to assess the digital maturity of the medical property resource management system in military healthcare. A multicenter descriptive study was conducted using quantitative and qualitative methods. Departmental medical and pharmaceutical organizations served as the subjects of the study. The digital maturity assessment was based on an adapted Digital Maturity Framework across 17 key criteria grouped into four blocks: attitudes and foundations (culture, leadership, budget, innovation); people, skills, and processes (capacity, recruitment, training, project management); systems and information (technology, data, reporting, understanding); and outcomes and user experience (communications, collaboration, optimization, internal systems, service delivery). For each of these, descriptive characteristics of five maturity levels were developed. Data collection methods included questionnaires and interviews with managers and employees responsible for medical property resource management, expert assessment by 42 experts, and random observation at the study sites. Significant variability in the digital maturity levels of organizations was revealed: most were at levels 1–3, and only a few had reached level 4. The lowest scores were observed for the following indicators: «culture», «leadership», «innovation», «data», «optimization», and «internal systems». It was found that military medical organizations under central control demonstrate higher levels of digital maturity. The main constraints include limited funding, an insufficiently developed material and technical base, a shortage of qualified personnel, and an incompletely defined unified departmental digitalization policy. The prevalence of digital maturity levels 1–2 indicates a fragmented and unsystematic digitalization of the medical property resource management system. Improving digital maturity requires the following: expeditious completion of a departmental digitalization strategy, centralization and standardization of the information technology infrastructure, development of human resources, an increase in targeted budget funding for systemic support, the creation of regional digitalization support centers, and the development of partnerships. A key requirement is the creation of a specialized departmental digital maturity assessment tool that takes into account the specifics of the medical property resource management system in military healthcare.