The attentional learning theory of Pearce and Hall () predicts more attention to uncertain cues that have caused a high prediction error in the past. We examined how the cue‐elicited pupil dilation during associative learning was linked to such error‐driven attentional processes. In three experiments, participants were trained to acquire associations between different cues and their appetitive (Experiment 1), motor (Experiment 2), or aversive (Experiment 3) outcomes. All experiments were designed to examine differences in the processing of continuously reinforced cues (consistently followed by the outcome) versus partially reinforced, uncertain cues (randomly followed by the outcome). We measured the pupil dilation elicited by the cues in anticipation of the outcome and analyzed how this conditioned pupil response changed over the course of learning. In all experiments, changes in pupil size complied with the same basic pattern: During early learning, consistently reinforced cues elicited greater pupil dilation than uncertain, randomly reinforced cues, but this effect gradually reversed to yield a greater pupil dilation for uncertain cues toward the end of learning. The pattern of data accords with the changes in prediction error and error‐driven attention formalized by the Pearce‐Hall theory.