We report a case of Rumpel-Leede (RL) phenomenon, - acute dermis capillary rupture, secondary to noninvasive blood pressure (NIBP) monitoring in a patient with type 2 diabetes mellitus (DM) and hypertension. The first most likely cause is vascular fragility in microangiopathy as a result of DM and chronic steroid use. The second is the increased venous pressure during cycling of the blood pressure cuff in a hypertensive state. Anesthesiologists need to be aware that acute dermal capillary rupture, although rare, can occur in patients with long-standing DM, hypertension and chronic steroid use.