Insulin therapy is not without side effects. In patients with complications on complex regimens, failure to attain adequate glycemic control exposes the patient to high risks and the considerable mental distress associated with failed injectable therapy. As clinicians, we felt it necessary to undertake a trial of newer therapies like insulin degludec, which according to published literature, appears to be superior to earlier basal analogs by fewer hypoglycemic episodes, better glycemic predictability, and genuine 24-hour coverage. Here we report on three cases seen in our own clinical practice where insulin degludec was used in patients experiencing inadequacies with their current basal insulin therapy (insulin glargine). Switching to insulin degludec resulted in clinically meaningful reductions in hypoglycemia, along with reduced fasting plasma glucose and glycosylated hemoglobin and improved satisfaction with treatment. We also explored the use of long-acting insulin in renal failure and the possibility of dose reduction when switching from existing basal insulin therapy.