Introduction. Skin popping (SP) is a popular technique for drug misuse, for its ease of administration and longer duration of effect. Skin infection is a well-described sequela of SP, but less is known about the more extreme sequelae of this practice. Methods. Five patients who engaged in SP requiring major surgical intervention were identified on case review to highlight extreme diseases resulting from the practice of SP. Each patient reported using heroin or tested positive for opioid on admission. Each patient admitted to practicing SP or maintained a shooter’s patch. A multidisciplinary approach was employed to care for the patient. Members of the departments of medicine, surgery, nursing, addiction medicine, infectious disease, rehabilitation, and social work collaborated in the complex management of each patient. Results. Five patients presented to Rush University Medical Center between 2017 and 2019 for complications of SP. All 5 patients were actively using nonprescription opioids; 2 were concurrently undergoing treatment for opioid use disorder. Recurrent SP led to failed surgical treatment in all but 1 patient. Surgical outcome was directly related to recidivism. Conclusion. The successful surgical management of severe sequelae of SP depends upon the successful management of the patient’s addiction. Multidisciplinary care by surgical, medical, psychiatric, addiction, nursing, rehabilitation, and social work specialists is necessary to achieve a successful outcome. Based on this experience, the author’s institution no longer offers nonurgent closure procedures to patients whose addiction is not well controlled.