A 70-year-old woman with type 1 diabetes presented to the endocrinology clinic for diabetes care. She had long-standing diabetes, which had been complicated by stage 3 chronic kidney disease, neuropathy, and advanced retinopathy with severe visual impairment. She was receiving a basal–bolus insulin regimen and monitored her blood glucose level four to seven times a day with a lancet for fingerstick testing and a talking glucometer. She had consistently performed multiple glucose tests daily for decades, which had led to soreness, bruising, and ultimately scarring and callus formation with hyperpigmentation of the fingertips. Her glycated hemoglobin level was 6%; she was not anemic and was not taking any medications that could have interfered with the glycated hemoglobin measurement. She saw her primary care doctor infrequently. This case highlights the importance of regular reeducation in diabetes self-management, even for patients with long-standing diabetes. The patient was advised to use the less painful lateral sides of her fingers for testing, to change her lancet with each use, and to adjust the depth of insertion of the lancet. In addition, relaxation of her glycated hemoglobin goal and consideration of the use of a voice-enabled continuous glucose monitor were recommended. Unfortunately, the patient did not return for follow-up.