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Programmed death protein-1 (PD-1) checkpoint inhibitors such as pembrolizumab and nivolumab are cornerstones to metastatic melanoma treatment, and they are often considered to be pharmacologically similar and interchangeable when it comes to designing chemotherapy regimens. In this case report, we describe a patient who had consistent immune reactions to nivolumab infusion but was able to tolerate pembrolizumab, without any reactions, when given hydrocortisone premedication. This case demonstrates a successful transition from one PD-1 checkpoint inhibitor to another with resolution of infusion-related reactions in a patient undergoing treatment for metastatic melanoma.