Symptomatic postural hypotension in diabetes is uncommon. When it does occur, it can prove debilitating and difficult to treat. We report here the therapeutic challenges encountered in managing a patient with severe postural hypotension secondary to diabetes-related autonomic neuropathy. A 69-year-old gentleman with a 23-year history of Type 1 diabetes mellitus and multiple microvascular complications was admitted with symptoms of severe postural hypotension. Cardiovascular autonomic testing confirmed the presence of severe autonomic neuropathy. He failed to respond to non-pharmacological measures, fludrocortisone, midodrine, octreotide, erythropoietin and increased caffeine intake. Eventually he was commenced on half a Cafergot suppository (giving him a dose of ergotamine 1 mg and caffeine 50 mg) which resulted in dramatic clinical improvement. Ergotamine may be considered in refractory cases of postural hypotension.