In military aircraft, control surface free play is defined as the angle the control surface can move about the control surface actuation axis when there is no load on the control surface. This free play arises from clearances between holes and pins in the control surface attachment method and backlash in the control surface actuator itself.If control surface stiffness is utilized in military aircraft flutter certification to prevent aeroelastic instability, the limits for safety free play and maximum allowable inertia characteristics should be set to avoid exceeding them throughout the aircraft’s operational life. Notably, safety free play for control surfaces, such as a horizontal stabilizer, that move entirely can be as small as 0.034 degrees.Recent advancements in the detailed design phase of military aircraft involve predicting control surface free play to meet requirements. In this paper, a methodology for applying the Monte Carlo method to predict free play in military aircraft is introduced. A simulated model mimicking a horizontal stabilizer was used to execute the simulation.When solving problems with a specific solution using the Monte Carlo method, the approximation converges after a sufficiently large number of simulations. This was utilized to fine the simulation count where the free play value converges for a simple attachment method and compared with geometrically derived free play. It was extended to determine the simulation count for a more complex attachment method similar to those found in real aircraft where geometrically deriving free play is challenging.Due to tolerances in hole and sin sizes in control surface attachments, considering the effects of tolerances is crucial for real-world application. This paper proposes analyzing conditions suitable for applying to actual aircraft by comparing Worst Case and Root Sum Square (RSS) conditions for cumulative tolerances in each group of holes and pins in control surface attachments.