We used a within-subjects design and multilevel modeling in two studies to examine the effect of prompting self-regulation, an intervention designed to improve learning from technology-delivered instruction. The results of two studies indicate trainees who were prompted to self-regulate gradually improved their knowledge and performance over time, relative to the control condition. In addition, Study 2 demonstrated that trainees’ cognitive ability and self-efficacy moderated the effect of the prompts. Prompting self-regulation resulted in stronger learning gains over time for trainees with higher ability or higher self-efficacy. Overall, the two studies demonstrate that prompting self-regulation had a gradual, positive effect on learning, and the strength of the effect increased as trainees progressed through training. The results are consistent with theory suggesting self-regulation is a cyclical process that has a gradual effect on learning and highlight the importance of using a within-subjects design in self-regulation. research.