Ensuring technical availability is crucial for military transport systems to perform their tasks under complex conditions, especially during armed conflict. In this paper, the authors propose a seven-state Continuous-Time Markov Chain (CTMC) model for the frontline operations area that describes transitions among the task-execution state, five repair levels, and the irreparable-damage state. The model accounts for the phase of operations, the operational zone, the direction of effort, terrain conditions, and the baseline loss rate as factors influencing system degradation. The analysis was conducted across 120 scenarios, and the model’s performance was evaluated by the time to reach a critical availability level below 0.50. The average availability time decreased from 17.27 days on flat terrain to 12.21 days in complex terrain (a reduction of 29.9%). A sensitivity analysis using the repeated-measures FANOVA method showed that terrain significantly affects the system’s operational capabilities. The results indicate that, in addition to the intensity of defensive operations, difficult terrain is the primary factor reducing the availability of transport systems.