Advancements in the field of design and control of lower extremity robotics requires a comprehensive understanding of the underlying mechanics of the human ankle. The ankle joint acts as an essential interface between the neuromuscular system of the body and the physical world, especially during locomotion. This paper investigates how the modulation of ankle stiffness is altered throughout the stance phase of the gait cycle depending on the environment the ankle is interacting with. Ten young healthy subjects with no neurological impairments or history of ankle injury were tested by walking over a robotic platform which collected torque and position data. The platform performed a perturbation on the ankle at 20%, 40%, and 60% of their stance phase in order to estimate ankle stiffness and evaluate if the environment plays a role on its modulation. The platform provided either a rigid environment or a compliant environment in which it was compliant and deflected according to the torque applied to the platform. Subjects adapted in different ways to achieve balance in the different environments. When comparing the environments, subjects modulated their stiffness to either increase, decrease, or remain the same. Notably, stiffness as well as the subjects’ center of pressure was found to increase with time as they transitioned from late loading to terminal stance (heel strike to toe-off) regardless of environmental conditions. This allowed for a model of ankle stiffness to be developed as a function of center of pressure, independent of whether a subject is walking on the rigid or compliant environment. The modulation of stiffness parameters characterized in this study can be used in the design and control of lower extremity robotics which focus on accurate biomimicry of the healthy human ankle. The stiffness characteristics can also be used to help identify particular ankle impairments and to design proper treatment for individuals such as those who have suffered from a stroke or MS. Changing environments is where a majority of tripping incidents occur, which can lead to significant injuries. For this reason, studying healthy ankle behavior in a variety of environments is of particular interest.