Triplet and higher-order multiple pregnancies can carry increased fetal and maternal complications. Reports of triplet pregnancies after kidney transplant are scarce and have been associated with perinatal complications. Presence of diabetes in such cases worsens both fetal and maternal outcomes. Here, we present a triplet pregnancy in a kidney transplant recipient with diabetes. We also reviewed the literature for causes, prevalence, and outcomes in association with chronic kidney disease, kidney transplant, and diabetes mellitus. The patient, a 31-year-female who received a living-donor kidney transplant, had a first-time pregnancy 6 years after transplant. Pregnancy was complicated by gestational diabetes, preeclampsia, and miscarriage. She continued to have postpartum-impaired glucose tolerance. She became pregnant again after 6 months but required insulin therapy during her third trimester. Pregnancy was terminated by cesarean section for a viable small boy. Two years later, she had triplet pregnancy after ovulation induction with clomiphene. Glycemic control was maintained using intensive insulin therapy guided by frequent home blood glucose monitoring (HbA1c was 5.8% at 22 wk). Both gynecologic care and nephrologic care were carried out through outpatient follow-up. Pregnancy was complicated by hypertension and mild renal dysfunction without proteinuria and ended in elective premature cesarean section at 32 weeks of gestation. She had 3 male babies with low birth weights (1320, 1380, 1275 g), with the largest baby developing sepsis and requiring an intensive care unit stay and then incubator for 49 days. The other 2 required incubators for 36 days. Their weights after 22 months were 9, 16, and 11 kg. The mother is now normotensive with normal renal function and impaired glucose tolerance. Care of diabetic kidney recipients with triplet pregnancy constitutes a special challenge requiring a multispecialty skilled team to ensure the best outcome.