IMPORTANCE Nearly 1400 medical students enter preliminary surgical residency each year; placing some of these students into categorical surgical training is an important component of building the future surgical workforce. OBJECTIVES To examine the training outcomes of preliminary residents in a university and Veterans Affairs surgical residency and to test the hypothesis that characteristics of these residents could be identified that would predict successful placement into categorical general surgical residency. DESIGN, SETTING, AND PARTICIPANTS A retrospective cohort of 66 nondesignated preliminary surgical residents who entered a research-intensive, university-based surgical training program with significant Veterans Affairs hospital experience between 2004 and 2012. MAIN OUTCOMES AND MEASURES Placement of preliminary residents into a categorical general surgical residency. RESULTS Of 66 nondesignated preliminary residents enrolled in our program during the study period, 57 completed a postgraduate year (PGY) 1 and 22 completed a PGY-2. A total of 21 residents (32%) secured categorical general surgical positions, 8 of 57 (14%) after PGY-1 and 13 of 22 (59%) after PGY-2, a significantly different rate (P < .001). Predictors of success in obtaining a categorical position included a PGY-2, United States Medical Licensing Examination step 2 score, year 1 American Board of Surgery In-Training Examination score, class rank, and prior graduate medical education. By multivariable analysis, only the PGY-2 was significant (P < .03). Residents who obtained categorical surgical positions after 1 preliminary year had significantly higher United States Medical Licensing Examination scores (mean [SD] step 1 score, 235.4 [23.5] vs 206.3 [16.2]; P < .02; step 2 score, 239.3 [21.2] vs 218.5 [16.1]; P < .05) but did not have higher year 1 American Board of Surgery In-Training Examination percentiles (mean [SD], 63.3 [33.3] vs 47.3 [30.8]; P < .34). CONCLUSIONS AND RELEVANCE Performing a PGY-2 preliminary year increases the chance for a preliminary surgical resident to obtain a place in a categorical surgical residency. Programs that offer preliminary positions should consider offering both PGY-1 and PGY-2 positions, because the PGY-2 increases the categorical surgical placement rate, especially for residents with lower test scores.