Scholars contend that effective teachers adapt their instruction to meet the particular needs of each student. However, little research has studied the ways in which teachers adapt their instruction or their reflections on these adaptations. This article describes a yearlong multiple case study focused on two teachers from different contexts: a Kindergarten teacher in a rural school in the Pacific Northwest region of the United States and a sixth-grade teacher in a suburban school in the Mid-Atlantic region of the United States. This research replicates previous studies of adaptive teaching. Two researchers used classroom observations, post-observation interviews, and artefacts to document these teachers' instructional adaptations and their reflections on these adaptations. Findings demonstrate the complexity of classroom instruction and the metacognitive processes teachers need to succeed in this complex environment. This study has implications for policy, teacher education, and professional development.