Context Vildagliptin is an oral anti-diabetic agent of the dipeptidyl-peptidase 4 inhibitor (DPP-4i) class of drugs. Together with glucagon-like peptide analogs (GLP1a), DPP-4i drugs are being known as incretin-based therapies (IBT). Results of clinical trials are conflicted about a potential association between IBT and acute pancreatitis. Case Reports We present the history, clinical progress, and diagnostic findings of two cases of acute pancreatitis occurred in a patient treated with vildagliptin. In both cases, other known causes of acute pancreatitis were ruled out. The first case was a woman who had a history of biliary pancreatitis, and the second case was a social drinker. Vildagliptin was suspected to be associated with acute pancreatitis since other identifiable causes were absent. Conclusions The combination of two pathophysiologically distinct processes can still associate and synergize in each individual.