The purpose of this research is to understand alternative certification candidates’ development as planners and implementers of Differentiated Instruction. This article presents three cases which introduces three female apprentices. The important role of self-regulation in apprentice development is an overarching conclusion in this study because the development of each of the other conditions (collegial relationships, classroom management, planning for a standard and student need, accepting feedback) was greatly influenced by the apprentice’s ability to self-regulate. Apprentices with strong self-regulatory capabilities demonstrated a stronger ability to plan and implement Differentiated Instruction. This stronger ability is possibly due to the fact that teachers who engage in self-regulatory behaviors are more likely to know what is going on with students, and lessons.