We report a case of a 23-year-old woman who sustained a stress fracture to the medial cuneiform. Isolated medial cuneiform fractures are extremely rare with less than 10 cases reported in the literature. The patient initially presented to an urgent care facility complaining of right midfoot pain that occurred while running. Radiographs obtained at the time showed no acute abnormality and the patient was told to resume normal activities. Several weeks later, she presented to urgent care again after exercising, this time unable to bear weight and with swelling and ecchymoses of the right foot. Plain radiographs were again normal, but a high suspicion for injury remained, so a magnetic resonance imaging of the foot was obtained. The advanced imaging showed an acute, non-displaced fracture of the medial cuneiform. Because the fracture was discovered soon after the injury and was non-displaced, she was treated conservatively and at 6-month follow up had returned to all pre-injury activities with no complaints. These rare fractures are often missed at initial presentation because they are usually not evident on plain radiographs. Unless more advanced imaging is obtained to rule out a fracture, a delay of diagnosis can occur resulting in additional morbidity for the patient. Level of clinical evidence: Level 5.