The digital transformation of local governments in developing countries presents major challenges for governance efficiency and inclusiveness. This study introduces the design and implementation of an innovative Decision Support System (DSS) for assessing and monitoring the digital maturity of 77 municipalities in Benin, across 12 administrative departments. The main objective is to develop a structured and interactive dashboard that allows decision-makers to identify digital strengths and weaknesses in their territories. The DSS is built upon a six-year longitudinal dataset (2016–2021) using 45 standardized indicators distributed across six governance domains: political and administrative governance, financial governance, participatory governance and gender, territorial and land management, supervisory relations, and cross-cutting indicators. The system processed 462 municipality-year observations, enabling multi-dimensional analytics including K-Means clustering and linear regression modeling. Results show significant disparities in digital readiness: 23% of municipalities are classified as “Advanced,” 34% as “Developing,” and 43% as “Basic.” The platform achieved 95% data consistency and 99.2% uptime, with 78% of users reporting enhanced understanding of their municipality’s digital maturity. Overall, the DSS offers a synthetic and objective perspective of municipal digital performance, significantly improving diagnostic efficiency and serving as a foundation for predictive modeling and evidence-based decision-making.