This chapter describes some specific adaptive procedures for tailoring levels of instructional guidance to individual levels of learner task-specific expertise to optimize cognitive resources available to learning. Recent studies in expertise reversal effect that were reviewed in previous chapters indicate that instructional design principles that benefit low-knowledge users may disadvantage more experienced ones. This reversal in the relative effectiveness of different instructional methods is due to the increase in cognitive load that is required for integration of presented supporting information with learners’ available knowledge structures. The major implication of these findings for multimedia design is the need to tailor levels of instructional support to individual levels of learner task-specific expertise. The procedures for adapting levels of instructional guidance suggested in this chapter have been developed in conjunction with empirically established interactions between levels of learner expertise and optimal instructional techniques and procedures. The chapter starts with the description of the processes and approaches to learning complex cognitive skills. The appropriate design models for learning complex skills are reviewed and different ways of varying levels of learner control in such models are described. The relations between levels of learner task-specific expertise and optimal levels of instructional guidance are then discussed. Also, empirical studies of the expertise reversal for instructional guidance and sequencing of learning tasks are reviewed. The completion tasks and faded worked examples are specific instructional methods used in the described studies for managing levels of instructional guidance in adaptive learning environments. Real-time monitoring of levels of learner task-specific expertise using rapid cognitive diagnostic methods was used in some of these studies.