We present the case of 60-year-old man with type 2 diabetes who developed blistering after two sequential exposures to linagliptin. Linagliptin is one of the dipeptidyl peptidase 4 (DPP-4) inhibitors, a group of oral hypoglycaemic agents used commonly for the treatment of type 2 diabetes. On the first exposure to linagliptin, he developed blisters on the hands which resolved after stopping the drug. After repeat exposure, he developed two large blisters on the left foot, which burst giving rise to secondary infection, requiring hospital admission for treatment. We discuss the latest research linking DPP-4 inhibitors with adverse skin reactions and the effect of ulcers on the morbidity and mortality of patients with diabetes. This case report highlights skin reactions as an important, rare and lesser known side effect of DPP-4 inhibitors.