Prior work has demonstrated the presence of hysteresis effects in the control of affordance-guided behavior, in that behavioral transitions around a critical action boundary vary with directions of change in said action boundary. To date, research on this topic has overlooked the influence of the global context on these phenomena. We employ an affordance-based reaching task, whereby participants were asked to move a target to a goal by passing through one of two apertures (size variable or size constant). It was found that the direction of change in the size of the variable aperture influenced the point of behavioral transitions, and this effect interacted with the location of a given goal. In addition, we considered fluctuations in the entropy of participants’ reach trajectories as a window into the nature of the behavioral phase transitions. Differences in the structure of entropy were found depending on the direction of change in the size variable aperture. These results are discussed in light of a dynamical systems approach, and recommendations for future work are made.