Adaptive guidance is an instructional intervention that helps learners to make use of the control inherent in technology-based instruction. The present research investigated the interactive effects of guidance design (i.e., framing of guidance information) and individual differences (i.e., pre-training motivation and ability) on learning basic and strategic task skills over time. 130 participants were randomly assigned to one of two types of adaptive guidance (autonomy-supportive, controlling) or a no-guidance condition while learning to perform a complex simulation task over nine consecutive trials. Results indicated that participants receiving controlling guidance acquired strategic task skills at a faster rate than participants receiving autonomy-supportive guidance or no-guidance. The design of adaptive guidance also moderated the effects of pre-training motivation and cognitive ability on learners’ acquisition of basic and strategic task skills. Specifically, autonomy-supportive guidance enhanced the positive effects of pre-training motivation on the acquisition of basic task skills, and controlling guidance enhanced the positive effects of cognitive ability on the acquisition of strategic task skills. Implications for research and practice are discussed.