While hypoglycemia is a frequent problem encountered in clinical practice, endogenous hyperinsulinemic hypoglycemia in a patient with diabetes is rare. Here, we describe such a case of recurrent hypoglycemia due to multifocal insulinoma (differential focal nesidioblastosis) in an adult patient with diabetes. The diagnostic dilemma, pitfalls in interpreting advanced imaging techniques, and difficulty in management of hyperinsulinemic hypoglycemia with underlying diabetes have been focused. The utility of acarbose and uncooked cornstarch to maintain euglycemia while combating two opposite sinister pathologies has been discussed. The novel association of antibody-negative Graves’ disease with insulinoma and nesidioblastosis is also reported in this study.