The human striatum has been implicated in processing reward-related information. More recently, activity in the striatum, particularly the caudate nucleus, has been observed when a contingency between behavior and reward exists, suggesting a role for the caudate in reinforcement-based learning. Using a gambling paradigm, in which affective feedback (reward and punishment) followed simple, random guesses on a trial by trial basis, we sought to investigate the role of the caudate nucleus as reward-related learning progressed. Participants were instructed to make a guess regarding the value of a presented card (if the value of the card was higher or lower than 5). They were told that five different cues would be presented prior to making a guess, and that each cue indicated the probability that the card would be high or low. The goal was to learn the contingencies and maximize the reward attained. Accuracy, as measured by participant's choices, improved throughout the experiment for cues that strongly predicted reward, while no change was observed for unpredictable cues. Event-related fMRI revealed that activity in the caudate nucleus was more robust during the early phases of learning, irrespective of contingencies, suggesting involvement of this region during the initial stages of trial and error learning. Further, the reward feedback signal in the caudate nucleus for well-learned cues decreased as learning progressed, suggesting an evolving adaptation of reward feedback expectancy as a behavior-outcome contingency becomes more predictable.