This study presents quantification of ankle stability as affected by environmental conditions in two degrees of freedom (DOF) with three distinct analysis techniques. Additionally, this study presents gender-specific trends for comparison. Intuitively, ankle stability decreased in less stable environments with a negative simulated stiffness. Female subjects generally suffered a greater loss of stability in moderately and highly unstable environments. Both gender groups exhibited greater stability in the sagittal plane than the frontal plane across the entire range of simulated stiffness's. Outcomes of this study are useful in the design of controllers for lower extremity physically-interactive robotics, understanding situations in which the ankle is likely to lose stability, and understanding the strengths and weaknesses of unique analysis techniques.