Contracture of muscle tendons is a common occurrence after compartment syndrome. However, these deformities usually affect all muscle-tendon units encompassed within a compartment and are commonly observed in the upper extremity. This video discusses the peculiar case presentation of a patient with an isolated contracture of the extensor hallucis longus (EHL) tendon after open reduction and internal fixation of a tibial stress fracture. Although the patient did not demonstrate traditional symptomology postoperatively, a possible missed diagnosis of compartment syndrome may have led to the deformity and sequelae. The patient presented to clinic 1 year postoperatively with severe extension contracture of the EHL and entrapment of the extensor digitorum longus, decreased strength and range of motion, and symptomatic hardware. The patient had decreased sensation in the first web space and the lateral aspect of the foot, with a positive Tinel sign at the anterior tibial incision, suggesting deep peroneal neuropathy. The symptomatic plate and screws were removed from the tibia before Z-plasty of the extensor tendons. The EHL and the extensor digitorum longus tendons were debrided, decompressed, and Z-lengthened a total of 2.5 cm to restore their natural excursion length. A short leg splint was applied, and the patient was instructed to remain non-weight bearing for 2 weeks, after which the patient was transitioned to a CAM boot for postoperative weeks two through six and was permitted to initiate active-assisted dorsiflexion. At 6 weeks postoperatively, the patient was transitioned out of the CAM boot, and active-resisted dorsiflexion was initiated. Acute compartment syndrome in the anterior compartment of the leg after a tibial fracture is not uncommon; however, isolated contractures of the extensor tendons are very rare. The etiology of this patient's contracture was most likely ischemic necrosis of the EHL that resulted from a missed diagnosis of acute compartment syndrome after open reduction and internal fixation. Localized ischemia typically results from trauma (fracture); however, it may result from postoperative bleeding, edema, or tight fascial closure. A missed diagnosis of acute compartment syndrome may lead to debilitating consequences for patients and medical-legal consequences for providers. Perioperative observation of intracompartmental pressure is essential in high-risk patients with a tibial fracture and patients who undergo elective procedures with the use of nerve blocks.