Case studies provide two views of adaptive expertise in teaching by analyzing the written reflections of teachers working in a reading clinic. David, with 20 years of experience, described adaptive judgments he made after careful description, data gathering, and analysis of students’ responses that allowed him to form hypotheses and craft instructional adaptations. David wrote his reflections from an objective stance that allowed him to focus closely and persistently on student learning, in spite of student avoidance behaviors and motivation challenges. Edward, with two years of experience, was negotiating the shift from a novice focus on teaching performance to a focus on student learning. The disequilibria he experienced while teaching in the reading clinic provided an opportune moment for enrichment of his practice, but Edward’s difficulty integrating newly learned instructional methods into his practice and resolving student motivation challenges led to difficulties in connecting his descriptive reflection to analysis and adaptation. Written reflection alone was not enough to help Edward resolve these difficulties. Edward’s case illustrates the tensions novices experience as they attempt to reconcile their growing base of experiences with new knowledge and the ongoing challenges of teaching.