Type 2 diabetes mellitus (T2DM) is a growing challenge across the globe. The disease process is amendable to lifestyle modifications in the early stages. If those changes fail to correct endocrine dysfunction, medical therapy is initiated. Initially, therapy for type 2 diabetes consisted of biguanides and sulfonylureas. With modern medicine, we have developed dipeptidyl peptidase-4 inhibitors, sodium-glucose cotransporter-2 inhibitors, and glucagon-like peptide 1 (GLP-1) receptor agonists. Dulaglutide is a GLP-1 receptor agonist that is sold under the brand name Trulicity. The most common side effect associated with Dulaglutide is gastrointestinal discomfort. We present a case of severe vaginal bleeding due to a rare side effect of Dulaglutide.A 44-year-old perimenopausal female with a past medical history of type 2 diabetes mellitus presented to the clinic after experiencing significant vaginal bleeding. The patient was unable to tolerate Metformin and Semaglutide in the past. The abnormal vaginal hemorrhage started one week after receiving the second dose of Dulaglutide. Her hemoglobin concentration fell significantly. Dulaglutide was immediately discontinued, and her vaginal bleeding stopped.This case documents the necessity of post-market surveillance to oversee the safety of recently approved medications by the Food and Drug Administration (FDA). Rare side effects can emerge in the general population that were not seen during clinical trials. Physicians should consider the possibility of adverse medication reactions when determining whether to start a new medication or a conventional one.