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Background and Purpose: Medication errors occur at alarming rates. Safe medication administration practices require more than observing patient safety rights and psychomotor skills. The purpose of this study was to explore the relationships between clinical judgment skills and reasoning processes and safe medication practices in senior nursing students. Methods: Using a cross-sectional design, 29 students from 3 schools of nursing watched a video simulation of a nurse administering medications in a clinical setting. At predetermined times, reflections on the medication administration practices were journaled. Journals were scored for clinical reasoning processes and clinical judgment using the Clinical Judgment Rubric-Reflective Journal (CJR-RJ) and for medication administration best practices. Results: Students scored low on the CJR-RJ (mean [SD], 5.2 [1.7]). We found a positive relationship between clinical judgment skills and safe medication practices (r = 0.39, t 27 = 2.94, P = .018). The clinical reasoning process of Interpreting was a significant indicator of best practices (b = 1.4, t 28 = 2.81, P = .010). Conclusion: Our findings suggest that students struggle to connect theory to practice, emphasizing the need to plan experiential learning opportunities for students to develop clinical reasoning, particularly in Interpreting, and judgment skills to prevent medication errors upon entry to practice.