Orthostatic hypertension refers to an increase in the blood pressure upon assuming an upright posture. This clinical condition has been understudied and is often underappreciated in clinical practice probably because of its unfamiliarity to many clinicians including subspecialists. We report a case of severely symptomatic orthostatic hypertension in a Caucasian female, which was likely secondary to an autonomic dysfunction caused by an underlying vascular adrenergic hypersensitivity and possibly also due to uncontrolled diabetes mellitus (causing baroreflex dysfunction associated with excessive sympathetic stimulation). The case work-up also illustrates a schematic diagnostic and management approach to this rarely encountered clinical entity.