Pupillometry is commonly used in research to determine how much mental effort an individual is exerting while completing tasks. Traditionally, larger pupils are associated with increased mental effort when completing more difficult tasks. However, little research has investigated how pupils change as individuals learn a new task. In theory, as one repeatedly completes a task, the task demands should reduce, reliance on working memory should decrease, and the task should become more automatic. This should translate to faster completion times and smaller peak pupil dilations. We tested this hypothesis by having participants complete multiple trials of a cognitive task that requires individuals to orient themselves in space relative to a target. We found that trial completion times and maximum pupil size significantly reduced across trials. These data suggest that measuring changes in pupil dilation may help researchers determine whether individuals have shifted from a learned procedure to an automatic processing of information when learning a new task.