PURPOSE: Objective assessment of technical skills in hand surgery has been lacking. This article reports on an Objective Structured Assessment of Technical Skills format of a multiple bench-station evaluation of orthopedic surgery residents' technical skills for 3 common upper extremity surgeries. METHODS: Twenty-seven residents (6 postgraduate year [PGY] 2, 8 PGY 3, 8 PGY 4, and 5 PGY 5) participated in the examination. Each resident performed surgery on a cadaveric specimen at 3 stations, trigger finger release (TFR), open carpal tunnel release, and distal radius fracture fixation. A board-certified hand surgeon evaluated trainee performance at each station, using a procedure-specific detailed checklist, a validated global rating scale, and pass/fail assessment. A resident post-testing evaluation was collected. RESULTS: Construct validity with correlation between year in training and detailed checklist scores was demonstrated for TFR and carpal tunnel release; between year in training and global rating scores for TFR and distal radius fracture fixation; and between year in training and pass/fail assessment for TFR. Criterion validity was demonstrated by the correlation between global rating scale scores, detailed checklist scores, and pass/fail assessment for TFR, carpal tunnel release, and distal radius fracture fixation. Time to complete the surgery was not correlated with surgical performance. Residents rated the multiple-station Objective Structured Assessment of Technical Skills format as highly educational. CONCLUSIONS: This study reports that a surgeon's ability to release a trigger finger does not correlate specifically to his or her ability to perform a carpal tunnel release or to perform plate fixation of a radius fracture. The results of this study would indicate that, for 3 different surgical simulations representing procedures of varying complexity, assessments by a single assessment tool is not adequate. To completely understand a resident's abilities, assessment by checklist (understanding the steps of the surgery), global rating scales (assessment of basic surgical skills in light of lesser or greater complexity surgeries), and pass/fail assessment (examination of adverse events) are all necessary components. TYPE OF STUDY/LEVEL OF EVIDENCE: Therapeutic II.