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Helping medical educators obtain and use assessment data to assist medical students, residents, and physicians in reducing diagnostic errors and other forms of ineffective clinical practice is of critical importance. Self-Regulated Learning–Microanalytic Assessment and Training is an assessment-to-intervention framework designed to address this need by generating data about trainees’ strategic processes (e.g., focusing on clinical task procedures), regulatory processes (e.g., planning how to do a task), and motivational processes (e.g., increasing confidence for performing a task) as they perform clinical activities. In this article, the authors review several studies that have used an innovative assessment approach, called self-regulated learning (SRL) microanalysis, to generate data about how trainees regulate their thinking and actions during clinical reasoning tasks. Across the studies, initial findings revealed that medical students often do not exhibit strategic thinking and action during clinical reasoning practice tasks even though some regulatory processes (e.g., planning) are predictive of important medical education outcomes. Further, trainees’ motivation beliefs, strategic thinking, and self-evaluative judgments tend to shift rapidly during clinical skills practice and may also vary across different parts of a patient encounter. Collectively, these findings underscore the value of dynamically assessing trainees’ SRL as they complete clinical tasks. The findings also set the stage for exploring how medical educators can best use SRL microanalytic assessment data to guide remedial practices and the provision of feedback to trainees. Implications and future research directions for connecting assessments to intervention in medical education are discussed.