Objective: To develop a methodology for minimizing costs, associated with additional investment attraction in the course of monitoring of accomplishment process and updating of digitalization program (Digitalization Programs DP). To consider the need for a strict quantitative justification and coordination of digitalization activities at various hierarchical levels of the projects. To show the necessity to solve tasks on calculating parameters of situational response to potential violations of DP accomplishment progress, to work out algorithms to determine rational relation between technical-technological procedures and control procedures. Methods: For to achieve the stated goals, stochastic dynamic programming method is applied; developed algorithms are based on the hypothesis on the possibility of distinguishing a law of DP stage duration distribution. Results: The system of algorithms, allowing to gradually select rational managing impacts while synchronization of usage of being additionally involved investments, combined with control procedures, is developed and tested. The methodology requires actualization due to inevitable changes in databases, containing information on links between randomized entities of next being predicted corrective measures, their cost and the assessment of being liquidated delay. To increase the calculation result reliability in parallel to realization of the developed algorithms, it is necessary to embody marketing research and efficiency model evaluation of various DP reboot options. Practical significance: An approach is proposed to provide for guaranteed implementation of transport system DPs within the given timeframes with minimal further investment. The developed algorithms make it possible to define not “deterministic” scheme of program reconfiguration but to carry out digitalization process situational management consistently. The developed algorithms can be recommended for practical use in the course of administrative-scientific accompaniment of the implementation of DP component project realization.