Procrastination is a self-regulation failure in which people irrationally delay intended actions which leads to lower performance, satisfaction from achievements, and quality of life. Trait procrastination is estimated to affect 15% to 20% of the total population, and previous studies have shown procrastination to be related to impulsivity, emotion dysregulation, and executive dysfunctions, making it a good nonclinical example of a self-regulation disorder. Our previous fMRI results revealed impaired error processing (lower error-related activity of the anterior cingulate cortex) and lack of ability to intensify executive-control during the punishment context (no increase in activity in prefrontal regions) in procrastinators. This led us to the question of whether procrastination is related to impaired learning on errors and punishments. Low (LP) and high (HP) procrastinating students took part in a modified monetary probabilistic reversal learning task with separated reward and punishment conditions. Half of the participants started with reward and half with the punishment condition. Several learning models and model-free measures were applied to the collected behavioral data. Results suggest lower flexibility in the learning task in HP subjects, which can further decrease during the punishment condition. Moreover, HP subjects who began with the punishment condition tended to be less flexible throughout the rest of the task. These results suggest that impaired learning from errors and punishments may prevent highly procrastinating subjects from correcting their behaviors and add to the persistence of procrastination. We also conclude that impaired learning on errors and punishments might be a more general mechanism underpinning other self-regulation disorders.