Hypoglycemia mitigation is critical for appropriately managing patients with diabetes. Advanced technologies are becoming more prevalent in diabetes management, but their benefits have been primarily judged on the basis of hemoglobin A1c. A critical appraisal of the effectiveness and limitations of advanced technologies in reducing both A1c and hypoglycemia rates has not been previously performed. The cost of hypoglycemia was estimated using literature rates of hypoglycemia events resulting in hospitalizations. A literature search was conducted on the effect on A1c and hypoglycemia of advanced technologies. The cost-effectiveness of continuous subcutaneous insulin infusion (CSII) and real-time continuous glucose monitors (RT-CGM) was reviewed. Severe hypoglycemia in insulin-using patients with diabetes costs $4.9-$12.7 billion. CSII reduces A1c in some but not all studies. CSII improves hypoglycemia in patients with high baseline rates. Bolus calculators improve A1c and improve the fear of hypoglycemia but not hypoglycemia rates. RT-CGM alone and when combined with CSII improve A1c with a neutral effect on hypoglycemia rates. Low-glucose threshold suspend systems reduce hypoglycemia with a neutral effect on A1c, and low-glucose predictive suspend systems reduce hypoglycemia with a small increase in plasma glucose levels. In short-term studies, artificial pancreas systems reduce both hypoglycemia rates and plasma glucose levels. CSII and RT-CGM are cost-effective technologies, but their wide adoption is limited by cost, psychosocial, and educational factors. Most currently available technologies improve A1c with a neutral or improved rate of hypoglycemia. Advanced technologies appear to be cost-effective in diabetes management, especially when including the underlying cost of hypoglycemia.