Diabetes is associated with increased risk of stillbirth and shoulder dystocia. Compared with uncomplicated pregnancies, diabetic patients have a 4-6x risk of stillbirth and 2-3x risk of shoulder dystocia. A 34 yo G2P0010 presented with a 40+3 wga IUFD with nonstandard antenatal glucose screening. Admission labs included a hemoglobin A1c of 6.6. She had a vaginal delivery complicated by a 30-minute shoulder dystocia that was not relieved by McRoberts, suprapubic pressure, Rubin II, Wood's Screw, or posterior arm delivery. Nitroglycerine was administered, after which Wood's Screw was successful resulting in delivery of an infant weighing 4190 grams (85th percentile for gestational age). A 31 yo G1 presented with a 37+1 wga IUFD. Her 28 wga three-hour GTT was notable for an elevated value at one hour (216 mg/dL). Admission labs included a hemoglobin A1c of 6.6. She had a vaginal delivery complicated by a 30-minute shoulder dystocia that was relieved via posterior axillary sling after failure of McRoberts, suprapubic pressure, Rubin II, Wood's Screw, and Gaskin's, resulting in the delivery of an infant weighing 3590 g (92nd percentile for gestational age). We present two cases of severe shoulder dystocia in patients who both presented with term IUFD and diabetic-range hemoglobin A1c. There is minimal literature on diabetic patients with pregnancies affected by both stillbirth and shoulder dystocia. These cases underscore the importance of glucose screening and control to prevent catastrophic obstetric outcomes.