Pregnancy and Cushing's syndrome rarely coexist. When they do, it is generally the result of the presence of an adrenal adenoma. Because of significantly increased morbidity and mortality in both the mother and fetus when hypercortisolism is present, it is imperative that it be treated when recognized. This treatment can take the form of definitive surgical treatment or temporary medical treatment until after delivery, both of which carry risks and benefits. Complicating the evaluation, however, it is well known that pregnancy itself can induce many of the symptoms and laboratory abnormalities associated with hypercortisolism. We present the case of a 35-year-old woman who was noted to have an adrenal mass before pregnancy, but then during evaluation became pregnant. Her case is particularly intriguing because she had only vague clinical symptoms and mild laboratory abnormalities but also had a complicating pituitary mass noted on MRI. We outline the evaluation process and eventual laparoscopic adrenalectomy during the second trimester in this unique and difficult case, and discuss risks and benefits of different treatment options for hypercortisolism during pregnancy.