Immune checkpoint inhibitors including programmed death protein 1 inhibitors show great therapeutic benefit for numerous advanced malignancies but can cause a spectrum of immune-related adverse events, with cutaneous toxicity being a common presentation. This report includes two cases of lung adenocarcinoma treated with pembrolizumab that developed rare presentations of diffuse bullous lichenoid dermatitis involving >50% total body surface area. These cases were successfully treated in the outpatient setting with oral dexamethasone and minimal interruption of pembrolizumab therapy, a more conservative approach than current guidelines suggest. J Drugs Dermatol. 2022;21(6):668-670. doi:10.36849/JDD.6715.