The association of pregnancy and Cushing’s disease (CD) is rare. A 28-year-old woman was admitted for clinical suspicion of Cushing’s syndrome. The investigations confirmed the diagnosis of CD with secondary hypogonadotropic hypogonadism due to an invasive pituitary macroadenoma. The patient underwent transsphenoidal adenomectomy, and histopathology showed an adrenocorticotropic hormone pituitary adenoma. Initial remission of CD ensued, and fertility was restored as the patient had 2 uncomplicated pregnancies. Five years and 10 months after surgery, a third spontaneous pregnancy was confirmed with underlying recurrent CD. Having mild hypercortisolism, CD was managed expectantly. The outcome was a healthy full-term neonate with no maternal complications during pregnancy or labor. Our case highlights the challenge faced by physicians of choosing the optimal approach to active CD in pregnancy. In cases where maternal and fetal complications are mild, conservative approach may be used and specific treatment can be postponed until after delivery.