Objectives: This study examines how the timing of Learning and Study Strategies Inventory (LASSI) administration affects scores on the 10 LASSI subscales, and whether or not there is a difference in the strength of association between subscale scores and student performance. Methods: The LASSI instrument was administered to 128 students during orientation at the beginning of the first and second years of medical school (M1and M2 years) for two classes. A paired t test was used to compare differences between the two administrations. To measure the strength of association between LASSI subscale scores and performance on overall biomedical sciences, National Board of Medical Examiners (NBME) Comprehensive Basic Sciences Exams (CBSE), and United States Medical Licensing Examination (USLME) Step 1, Pearson product-moment correlation analyses were performed. Results: There is a significant difference between LASSI subscale scores at the beginning of M1 and at the beginning of M2. There were more significant correlations between LASSI subscale scores at the beginning of M2 with performance on overall biomedical sciences, NBME CBSE, and USMLE Step 1 exam. Significant associations were observed between LASSI subscales Anxiety, Selecting Main Ideas, and Test Strategies with students’ performance on overall biomedical sciences, NBME CBSE, and USLME Step 1. Information Processing was also correlated with NBME CBSE and USMLE Step 1. Conclusions: Assessing medical students’ learning and study-strategy skills is more accurate after a medical school experience than at the start of medical school. Anxiety, Selecting Main Ideas, and Test Strategies are correlated with students’ performance on both internal and external performance measures. © 2017, International Association of Medical Science Educators.