The goal of zone II flexor tendon surgery is to perform a repair with sufficient strength to withstand the forces encountered during rehabilitation. Postoperative rerupture and adhesion formation may lead to reoperation. This study aimed to determine the factors associated with reoperation after primary zone II flexor tendon repair. In this retrospective case series, a total of 252 fingers in 201 patients underwent zone II flexor tendon repair. A medical record review was performed to collect data regarding patient demographics, injury and treatment characteristics and postoperative complications including reoperation. Reoperation was defined as any unplanned surgical procedure performed after initial flexor tendon repair. There were 49 fingers (19%) in 42 patients that underwent reoperation at a median of 5.5 (interquartile range: 2.8-7.9) months. Older age, workers' compensation, and a Kessler-type repair of the flexor digitorum profundus were independently associated with reoperation. In vitro studies suggest that Kessler-type repairs are inferior compared with other suture configurations. Our study demonstrates a clinical correlation to these biomechanical studies. Our results suggest that Kessler-type repairs are inferior compared with non-Kessler-type repairs, due to postoperative complications requiring secondary surgeries.