The paper summarizes preliminary results of an in-depth study designed to explore the complex dynamics of hypothetical "motivated regulatory failure", presenting them in terms of different types of procrastination experience. Our model of motivated regulatory failure, building mainly on the reactance theory and self-determination theory, proposes that situational changes in goal preference may actually result from (motivated) disruptions of regulatory structure, rather than causing them. 112 students of psychology (80 female; mean age = 23.0) completed a large set of self-report measures as a part of a self-exploration project embedded in a course in motivation psychology. They were also asked to write a short essay describing their study experience in general. The quantitative data were entered into cluster analysis using maximized Euclidean distances as criterion, which produced several clusters of procrastinators. Variables for the clustering were chosen to maintain balance among the salient characteristics: academic procrastination, psychological reactance, personal standards, need of arousal, primary and associated aversion, achievement motivation, trait anxiety, self-esteem, mastery goals, self-efficacy, and test anxiety. The clusters were further compared according to other relevant criteria, including self-determination variables, self-regulation, and various aspects of study experience. Two clusters that consistently appeared throughout different samples included active procrastinators (high need of arousal, high self-efficacy, and low anxiety) and aversive procrastinators (low mastery motivation and high primary aversion). The third group of procrastinators, which is of special interest to our research, included students with paradoxically high intrinsic and mastery motivation, high anxiety levels, and strong aversion by association. Interestingly, the cluster turned out to contain two subgroups with very different self-determination profiles and emotional consequences. The paper, by introducing and describing all of these types of students in both quantitative terms and qualitative illustrations, attempts to discuss the core motivational dynamics behind irrational delay.