This case report discusses dumping syndrome in the postbariatric mother. Diagnostically a challenge, the symptoms of postprandial hypoglycaemia mimic common early gestation complaints and may go undiagnosed, thus requiring a high index of suspicion. As weight-loss surgery gains traction, it is pertinent to note at booking and followups. The pregnancy is at-risk and multidisciplinary team management is central. The mainstay of management remains diet modification. There have been case reports of successful medical treatment of dumping syndrome in pregnancy with good maternal and fetal outcomes. However, more data is needed regarding the usage of these medical treatments in pregnancy.