Pregnancy in women with Cushing’s syndrome (CS) is uncommon. It is associated with significant maternal and fetal complications. Pregnancy‐induced Cushing’s syndrome is exceptionally rare with fewer than ten cases reported in the world literature and none in Australia or New Zealand. We describe a woman with possible recurrent pregnancy‐induced CS complicating five pregnancies over a 7‐year period. We discuss the changes in the hypothalamic–pituitary–adrenal axis during normal pregnancy together with the diagnosis, aetiology and management of CS in pregnancy.