Rerupture after cortical button fixation and whipstitch suture technique is a rare complication of distal biceps tendon repair. The tendon-bone fixation construct can fail for various reasons, including cortical breach, pull out or disengagement of a cortical button, suture breakage, or knot slippage. Occasionally, a cut-through of the tendon substance by the high-tensile strength suture material, called the 'cheese-wire' effect, can happen, especially with premature loading during the early postoperative period. The clinical presentation is more subtle, and the rerupture may go unnoticed. A high index of suspicion and a low threshold for ordering a magnetic resonance imaging (MRI) scan are necessary for a prompt diagnosis and early treatment. We describe the management of a reruptured distal biceps in an active male that happened in the early postoperative period, along with a critical analysis of the failure pattern and potential preventive measures.