The underestimation of depth in virtual environments at mediumield distances is a well studied phenomenon. However, the degree by which underestimation occurs varies widely from one study to the next, with some studies reporting as much as 68% underestimation in distance and others with as little as 6% (Thompson et al. [38] and Jones et al. [14]). In particular, the study detailed in Jones et al. [14] found a surprisingly small underestimation effect in a virtual environment (VE) and no effect in an augmented environment (AE). These are highly unusual results when compared to the large body of existing work in virtual and augmented distance judgments [16, 31, 36–38, 40–43]. The series of experiments described in this document attempted to determine the cause of these unusual results. Specifically, Experiment I aimed to determine if the experimental design was a factor and also to determine if participants were improving their performance throughout the course of the experiment. Experiment II analyzed two possible sources of implicit feedback in the experimental procedures and identified visual information available in the lower periphery as a key source of feedback. Experiment III analyzed distance estimation when all peripheral visual information was eliminated. Experiment IV then illustrated that optical flow in a participant’s periphery is a key factor in facilitating improved depth judgments in both virtual and augmented environments. Experiment V attempted to further reduce cues in the periphery by removing a strongly contrasting white surveyor’s tape from the center of the hallway, and found that participants continued to significantly adapt even when given very sparse peripheral cues. The final experiment, Experiment VI, found that when participants’ views are restricted to the field-of-view of the screen area on the return walk, adaptation still occurs in both virtual and augmented environments.