System obsolescence issues are a routine occurrence, especially for systems with a high utilization of commercial electronic components or software applications with a long operational life. The extended length of a system's development can often result in obsolescence well before system production and fielding begins. Obsolescence affects individual electronic components and availability of materials, as well as access to experienced personnel, processes, and software. Legacy application software obsolescence is influenced by multiple factors. Included in these factors are hardware obsolescence, increased software maintenance, commercial off‐the‐shelf software obsolescence, growth in technical debt, growth in complexity, and a lack of embedded business rule documentation. These criteria influence subjective management decisions in the remediation of current or future obsolescence risk. A multicriteria decision‐making (MCDM) approach is proposed to evaluate the impact of multiple obsolescence elements over the life cycle of a software application with consideration for the knowledge, preference, and subjectivity of experts to better inform the risk assessment and timing of future mitigation strategies. The resulting MCDM score provides a break point for a quantifiable increase in obsolescence risk.