Rumpel-Leede (R-L) phenomenon is the rare event in which the small dermal capillaries of an extremity rupture in response to application of a compressive device to that extremity, such as when inflating a cuff during noninvasive blood pressure monitoring or when applying a tourniquet to draw blood. This capillary rupture results in formation of a petechial rash distal to the compressive device. R-L phenomenon is believed to occur most often in patients with underlying vascular disease, such as diabetes mellitus or thrombocytopenia. R-L phenomenon is most often benign, though it may rarely be associated with pain and discomfort. There is no treatment for this condition apart from treatment of the underlying vascular disease or thrombocytopenia. We report a 57-year-old woman who presented with hypertensive urgency and experienced R-L phenomenon during blood pressure cuff inflation.