This study investigated the effects that self-regulation prompts and goal orientation may exhibit on self-regulatory processes and subsequent learning. Specifically, a moderated mediation model was developed to explain how self-regulation prompts interact with prove performance goal orientation to affect two mediational processes, time on task and self-regulatory activity, and ultimately impact learning within a learner-controlled e-learning environment. To assess these hypotheses, an online Microsoft Excel instructional program was developed wherein 197 participants had control over when and where they completed training, the content they reviewed, the delivery medium (text-based or video-based), and the sequencing and pace at which they progressed through training. Participants in the experimental condition were periodically asked questions (i.e., self-regulation prompts) designed to encourage self-assessment of learning progress and strategies. All participants completed questionnaires before and after training. Findings did not support the hypothesized model. Implications and limitations as well as recommendations for future research will be discussed.