Diabetic cardiac autonomic neuropathy (CAN) is caused by damage to the autonomic nerve fibers that innervate the heart and blood vessels, leading to abnormalities in heart rate control and vascular dynamics. CAN encompasses symptoms such as exercise intolerance, orthostatic hypotension, cardiac denervation syndrome, and nocturnal hypertension. Neurogenic orthostatic hypotension (nOH), resulting from severe diabetic CAN, can cause symptomatic orthostatic hypotension. The management of orthostatic hypotension primarily focuses on preventing severe symptoms, such as syncope and falls. It is equally important to address nocturnal supine hypertension, as it can exacerbate morning orthostatic hypotension. The management strategies for these conditions often complicate each other, highlighting the intricate and delicate nature of treating severe orthostatic hypotension associated with diabetic CAN. We present the case of a 55-year-old male with symptomatic orthostatic hypotension and coexisting nocturnal supine hypertension caused by severe, advanced diabetic CAN.