Background: Pectoralis major tendon ruptures have become increasingly common injuries among young, active individuals over the past 30 years; however, there is presently a paucity of reported outcome data. We investigated the ability to return to full preoperative level of function, complications, reoperation rates, and risk factors for failure following surgical repair of the pectoralis major tendon in a cohort of young, highly active individuals. Methods: All U.S. active-duty military patients undergoing pectoralis major tendon repair between 2008 and 2013 were identified from the Military Health System using the Management Analysis and Reporting Tool (M2). Demographic characteristics, injury characteristics, and trends in preoperative and postoperative self-reported pain scale (0 to 10) and strength were extracted. The ability to return to the full preoperative level of function and rates of rerupture and reoperation were the primary outcome measures. Univariate analysis followed by multivariate analysis identified significant variables. Results: A total of 257 patients with pectoralis major tendon repair were identified with a mean follow-up (and standard deviation) of 47.8 ± 17 months (range, 24 to 90 months). At the time of the latest follow-up, 242 patients (94%) were able to return to the full preoperative level of military function. Fifteen patients (5.8%) were unable to return to duty because of persistent upper-extremity disability. A total of 15 reruptures occurred in 14 patients (5.4%). Increasing body mass index and active psychiatric conditions were significant predictors of inability to return to function (odds ratio, 1.56 [p = 0.0001] for increasing body mass index; and odds ratio, 6.59 [p = 0.00165] for active psychiatric conditions) and total failure (odds ratio, 1.26 [p = 0.0012] for increasing body mass index; and odds ratio, 2.73 [p = 0.0486] for active psychiatric conditions). Conclusions: We demonstrate that 94% of patients were able to return to the full preoperative level of function within active military duty following surgical repair of pectoralis major tendon rupture and 5.4% of patients experienced rerupture after primary repair. Increasing body mass index and active psychiatric diagnoses are significant risk factors for an inability to return to function and postoperative failures. Level of Evidence: Therapeutic Level IV. See Instructions for Authors for a complete description of levels of evidence.