Phenomena related to positive emotional valence and reward responsiveness have been extensively studied in psychology. These constructs have been linked to midbrain dopaminergic pathways central to the literature on psychopathologies and development, and their measurement is a key interest in task-based fMRI. One such task, used for almost twenty years, is the Monetary Incentive Delay (MID) task. By cueing and delivering performance contingent reward, this task has been demonstrated to elicit robust and distinct activation of neural circuits involved in different phases of reward responsiveness (e.g. anticipation and outcome). Despite the broad application of the MID task, systematic evaluations of common task contrasts have been limited to between study comparisons of mean level (or group level) activation maps. In this study, we systematically examine within-task and between-contrast differences in MID task activation maps and how these differences impact inferences about their correlations with psychological characteristics. In a sample of 104 participants (Age Mean = 19.3, SD = 1.3; Female 57%), we evaluate similarities between contrasts in group- and individual-level activation maps, region-of-interest activations and their correlations with psychological characteristics. Our findings demonstrate more similarities than differences between positive and negative cues during the anticipation contrast, dissimilarity between some positive anticipation contrasts, a robust deactivation effect in the outcome phase, and behavioral associations that are less robust than previously thought. This work has practical implications for helping researchers interpret prior MID studies and make more informed a priori decisions about contrasts to focus on in future work. Consistent with other recent findings from large neuroimaging samples, it also suggests that researchers using the MID to identify brain-behavior relationships may have to more carefully specify their contrasts in advance in order to reliably detect small, variable effects.