<h3>Clinical Presentation</h3> A 13-year-old male presented with the chief complaint of pain and facial swelling on the left side. His medical history was significant for chronic recurrent multifocal osteomyelitis (CRMO) and hospitalization for recurrent right facial swelling, tenderness, and chronic ankle pain. <h3>Differential Diagnosis</h3> CRMO can mimic infective osteomyelitis, thus unnecessarily subjecting the patient to a prolonged course of antibiotics, radiation exposure, and multiple biopsies. <h3>Diagnosis and Management</h3> Extraoral radiographs: Normal bone pattern, no evidence of periosteal reaction and mild left-sided soft tissue swelling. Magnetic resonance imaging (MRI): Postcontrast T1-weighted fat-suppressed 2017: High signal from the marrow of the right mandibular body and ramus and surrounding muscles representative of edema. Noncontrast T2-weighted fat-suppressed 2018: Persistent high signal in the marrow of the right mandibular body and ramus, with a resolution of muscular edema; the new hyperintense signal in the marrow of the left mandibular body. Bone scan: Phases 2 and 3: Increased tracer uptake along the right mandible and the right calcaneus and epiphyses of the long bone. <h3>Discussion</h3> Familiarity with the clinical and radiographic findings of CRMO greatly increases the likelihood of early diagnosis, appropriate treatment, and avoidance of multiple unnecessary procedures.