A 39 years old lady who started to develop hypoglycemia three month following gastric bypass surgery. She is known to have Type 2 DM, dyslipidemia hypertension and Hirsutism. Her weight on presentation was 93.5 kg (pre operation was 104 kg) and Ha1c was 6% (pre operation was 10.5%). She was off diabetes medications. Hypoglycemia mainly fasting some readings < 3 mmol/l, with symptoms (diaphoresis, fatigue and weakness) but sometime hypoglycemia occur 23 h post prandial and also at night. She was started on Acarbose 25 mg three time daily (TID), Fibers enrichment of meals and continuous glucose monitoring inserted (CGM). Hypoglycemia persisted and we added Verapamil 120 mg and Acarbose increased to 50 mg TID. Two weeks later, because of recurrent hypoglycemia (glucose of 3.9 mmol/l), she was admitted. Her fasting insulin and C-peptide level were normal and Acarbose increased to100 mg TID. In Two weeks follow up her CGM revealed multiple hypoglycemic events, mostly asymptomatic and nocturnal & she admitted again. Her Lab glucose was 2.76 mmol/l, with concomitant inappropriately high Insulin level 8.4 mIU/l and detectable but not extremely elevated C-peptide 0.33 nmol/l. Normal adrenal response to ACTH stimulation and normal renal function. Urine screen for sulfonylureas screen and insulin AB were normal. We started Octreotide 50 mcg Q11 TID and continued on Acarbose & Verapamil. However, hypoglycemia persisted and Diazoxide 50 mg has been started and increased gradually. Her hypoglycemia improved and Acarbose and Octreotide stopped. Shortly following discharge, she re-presented with frequent hypoglycemic events on Diazoxide 150 mg, therefore, Octreotide was stated again. Pancreatic MRI was negative. Hypoglycemia, occurring after gastric bypass surgery, is challenging for patients and physicians . Acarbose and dietary modifications are the initial treatment and incomplete response need reassessment and father testing and additional pharmacological management.