Supine hypertension with orthostatic hypotension (SH-OH) represents a paradoxical and challenging form of blood pressure (BP) dysregulation, particularly in patients with autonomic failure such as Parkinson's disease (PD). This is a case of an 85-year-old male veteran with PD and multiple comorbidities, including coronary artery disease, diabetes with neuropathy, obstructive sleep apnea, and chronic kidney disease, who exhibited severe SH-OH characterized by supine systolic BP exceeding 200 mmHg and orthostatic systolic dropping to 110 mmHg. His symptoms included syncope, dizziness, and headaches. Pathophysiology involves autonomic dysfunction with impaired baroreflex, residual sympathetic activity, and dysregulation of the renin-angiotensin-aldosterone system. Management was tailored to address both SH and OH. Nonpharmacologic strategies included head-of-bed elevation, fluid and salt supplementation, compression garments, and continuous positive airway pressure therapy, which also targeted his untreated OSA and helped reduce sympathetic overactivity. Pharmacologic interventions required fine-tuning due to the complex interplay of SH and OH. Fludrocortisone was contraindicated due to a recent upper gastrointestinal bleed. Pyridostigmine was trialed but discontinued after evidence of atrioventricular block. The final regimen involved clonidine and hydralazine at bedtime for SH, along with midodrine timed around daytime activity for OH. This case highlights the nuanced, often counterbalancing management required in SH-OH, especially in elderly patients with neurodegenerative disease and cardiovascular risk. Multimodal therapy, individualized to avoid exacerbating one component while treating the other, remains essential. Further research is needed to optimize care strategies and improve the quality of life in this vulnerable population.