Personalized prompting research has shown the significant learning benefit of prompting. The current paper outlines and examines a personalized prompting approach aimed at eliminating performance differences on the basis of a number of learner characteristics (capturing learning strategies and traits). The learner characteristics of interest were the need for cognition, work effort, computer self-efficacy, the use of surface learning, and the learner’s confidence in their learning. The approach was tested in two e-modules, using similar assessment forms (experimental n
= 413; control group n
= 243). Several prompts which corresponded to the learner characteristics were implemented, including an explanation prompt, a motivation prompt, a strategy prompt, and an assessment prompt. All learning characteristics were significant correlates of at least one of the outcome measures (test performance, errors, and omissions). However, only the assessment prompt increased test performance. On this basis, and drawing upon the testing effect, this prompt may be a particularly promising option to increase performance in e-learning and similar personalized systems.