The article presents a scientific and practical study of the analytical tools for assessing the strategic development of critical infrastructure enterprises. The modern environment of the functioning of critical infrastructure enterprises in the regions of Ukraine is characterized by a high degree of uncertainty, the impact of systemic crises, resource shortages and the need to ensure the continuity of vital economic and financial processes. To overcome these limitations, this study aims to expand the analytical tools for managing the strategic development of critical infrastructure enterprises, providing a comprehensive assessment of their strategic stability, adaptability and development potential in conditions of uncertainty. The methodological basis of the study is a systematic approach, methods of economic and comparative analysis, integrated assessment of indicators, scenario modeling and expert assessment. According to the results of the study, key strategic areas for monitoring the effectiveness of the strategy for adaptive and effective development of critical infrastructure enterprises have been identified. A theoretical and methodological basis for monitoring has been created, which involves the integration of quantitative assessments, analysis of time trends and meaningful interpretation of the results obtained. A set of indicators and a methodological approach to assessing the effectiveness of the adaptive and effective development strategy have been developed. The scientific contribution of the study lies in the combination of three interrelated levels of analytical work: quantitative assessment of the level of enterprise development, qualitative interpretation of the obtained integral indicator and strategic interpretation of the results using the monitoring matrix. The practical significance of the results lies in the possibility of using the proposed analytical tools in the system of strategic enterprise management for regular assessment of development results, identification of problem areas and substantiation of management decisions.