Nurse educators have been challenged to creatively implement the clinical judgment model (CJM) across the curriculum. Opportunities exist to utilize rich patient data in clinical debriefing. Rolling Through the Complications with the CJM, a scripted clinical debriefing tool, was created to help students think beyond the clinical day and apply clinical judgment to potential complications. In a pilot study, five medical-surgical clinical instructors implemented the clinical debriefing tool. Survey responses from 29 students following the clinical debriefing expressed the activity was a positive experience encouraging focused analysis beyond typical post-conference discussions. Comments focused on critical thinking, collaborative learning, application to future practice, and holistic care. Clinical post-conferences offer excellent opportunities to implement scripted debriefing encompassing the CJM. [J Nurs Educ. 2024;63(X):XXX-XXX.].