The apparent difficulty that humans experience when asked to manage dynamic complexity might be related to their inability to discriminate among familiar classes of objects (i.e., flawed recognition). In this study we examined the change in individuals’ recognition ability, as measured by the change in the similarity of decisions they made when confronted repeatedly with consistent dynamic situations of varying degrees of similarity. The study generated two primary findings. First, decisions became increasingly similar with task practice, a result that suggests gradually improving discrimination by the participants. Second, the similarity was determined by the interaction of many task features rather than individual task features. The general principles highlighted by this study are applicable to dynamic situations. For example, with practice, decision makers should be able to learn to identify the time at which to intervene to achieve the maximal effect during dynamic decision making.