SAPHO syndrome is a dermatological, musculoskeletal and rheumatological spectrum consisting of Synovitis, Acne, Pustulosis, Hyperostosis and Osteitis. SAPHO is commonly seen in children and young to middle-age adults, but it can present at any age. It is a rare disease that often has a delayed diagnosis due to the varying clinical manifestations. Especially concerning the adolescent population, common symptoms like acne and bone/joint pain could be misinterpreted as pubertal changes. The patient is a 19-year-old Pakistani male being treated under palliative care for SAPHO syndrome. At the age of 11, the patient had an onset of severe cystic acne. At age 13, he developed a draining cyst in his perianal region. Despite negative cultures, it was treated as a MRSA infection with several rounds of antibiotics producing little improvement. One month later, he spiked a fever and additional draining lesions developed in his inner thighs. There was a concern for possible fistulas secondary to Crohn’s disease but a complete work-up was negative except for a thickened distal ileum on MRI. At this point, patient was treated with Prednisone for a presumed diagnosis of Crohn’s resulting in incidental improvement of the cysts. In November 2011, the patient developed severe back pain that was associated with morning stiffness. A lumbosacral MRI showed osteitis, which ultimately lead to the diagnosis of SAPHO Syndrome. The patient was started on infliximab, which improved his back pain but not his cysts, one of which required an I&D procedure. When infliximab was held for wound healing by secondary intention, the back pain returned accompanied by anterior chest wall and sternal pain. When his pain was not alleviated with the reintroduction of infliximab, he was found to have anti-infliximab antibodies. Other pharmacological therapies of methotrexate, anakinra, certolizumab, adalimumab, and antibiotic prophylaxis were tried with varying amounts of responsiveness but without significant improvement. The patient was recommended for palliative care and is currently being managed for pain, major depression, weight loss, and insomnia. The course of SAPHO syndrome varies from patient to patient. Some experience symptomatic flares while others have a continuous course. Treatment is empiric with NSAIDs being first-line followed by various courses of corticosteroids, DMARDS, and biologics. In treating chronic inflammatory syndromes in the pediatric population, the effects of these long-term regimens should be of concern. Initiation in childhood maximizes the chance of extended use complications, such as developing anti-infliximab antibodies as in this case. Persistent SAPHO syndrome can cause severe detriment to general well-being, mentally and physically, especially in the pediatric population. With the potential for refractory cases, current management should not only focus on curative therapies but also on improvement of quality of life through palliative care.