Assessing the accuracy of the logistics cycle is one of the most important areas of research in logistics and supply chain management. Currently, asymmetrical distributions of the operations execution time and, accordingly, the entire logistics cycle are becoming increasingly widespread. The paper proposes an analytical model and an algorithm for assessing the probability of completing the logistics cycle based on the “Just-In-Time” concept. The calculations carried out demonstrated that the greatest interest is in considering asymmetry and accounting superposition when approximating the execution time of logistics cycle operations. The calculations of deviations in the execution time of logistics cycle operations made it possible based on the “Just-In-Time” concept to clarify the ranges of logistics cycle time values, as well as to show the deviations of probabilistic estimates taking into account a given time window for the execution of logistics cycles. The obtained results convincingly indicate the presence of deviations in the probabilistic assessment of the logistics cycles implementation based on existing and proposed approaches.