There have been several hundred rollovers in military vehicles in the last decade of deployment, of which approximately fifty percent are fall-based that occur during off-road operations. Off-road fall-based rollovers occur at lower speeds when the soft road gives way underneath the vehicle on one side as the soil is unable to support the vehicle load. During these sudden events, drivers, who are generally not prepared, often make impromptu driving decisions that quickly lead to rollover situations. A real-time driving simulator can be instrumental in reducing rollover incidents when used as a training tool. The current research takes a comprehensive approach in understanding this rollover phenomenon, and develops a novel real-time terramechanics approach with a vehicle dynamics model validated on the N-post shaker. TARDEC’s Ride Motion Simulator is then used to examine rollover performance in response to various driving styles under various soil conditions. The results are summarized.