Available behaviors are determined by the fit between features of the individual and reciprocal features of the environment. Beyond some critical boundary certain behaviors become impossible causing sudden transitions from one movement pattern to another. Parkour athletes have developed multiple movement patterns to deal with their momentum during landing. We were interested in whether drop distance would cause a sudden transition between a two-footed (precision) landing and a load-distributing roll and whether the transition height could be predicted by dynamic and geometric characteristics of individual subjects. Kinematics and ground reaction forces were measured as Parkour athletes stepped off a box from heights that were incrementally increased or decreased from 0.6 to 2.3 m. Individuals were more likely to roll from higher drops; those with greater body mass and less explosive leg power, were more likely to transition to a roll landing at a lower height. At some height a two-footed landing is no longer feasible but for some athletes this height was well within the maximum drop height used in this study. During low drops the primary task constraint of managing momentum could be achieved with either a precision landing or a roll. This meant that participants were free to select their preferred landing strategy, which was only partially influenced by the physical demands of the task. However, athletes with greater leg power appeared capable of managing impulse absorption through a leg mediated strategy up to a greater drop height.