I usually say to my residents that when I was a resident myself, I was much more confident at diagnosing and treating Cushing’s syndrome than I am today! This statement aims at pointing out that the deeper you go in dealing with clinical, laboratorial, and image aspects of the differential diagnosis of the many etiologies of the syndrome, as well as the various treatment modalities, the more you will encounter cases that are exceptions to the rules, leading to diagnosis and treatment pitfalls. However, notwithstanding that, only insights provided by experts will help physicians dealing with Cushing’s syndrome to provide better care to their patients, avoiding the above-mentioned pitfalls.