Previous studies have identified a negative potential in the event-related potential (ERP), the error-related negativity (ERN), which is claimed to be triggered by a deviation from a reward expectation. Furthermore, this negativity is related to shifts in risk taking, strategic behavioral adjustments, and inhibition. We used a computer Blackjack gambling task to further examine the process associated with the ERN. Our findings are in line with the view that the ERN process is related to the degree of reward expectation. Furthermore, increased ERN amplitude is associated with the negative evaluation of ongoing decisions, and the amplitude of the ERN is directly related to risk-taking and decision-making behavior. However, the findings suggest that an explanation exclusively based on the deviation from a reward expectation may be insufficient and that the intention of the participants and the importance of a negative event for learning and behavioral change are crucial to the understanding of ERN phenomena.