We report a case of Rumpel-Leede phenomenon, or acute dermis capillary rupture, secondary to noninvasive blood pressure monitoring in a patient with type 2 diabetes mellitus. The most likely cause was increased venous pressure during cycling of the blood pressure cuff during a hypertensive state. Anesthesiologists need to be aware that acute dermal capillary rupture, although rare, can occur in patients with thrombocytopenia and/or long-standing diabetes.