<p>Endometriosis, a chronic and multifocal inflammatory condition with a substantial estrogen-dependent component, is often linked to infertility. Some patients with endometriosis may require surgical intervention or assisted reproductive technologies to conceive. Although many patients who achieve pregnancy have relatively uncomplicated outcomes because of the progesterone-induced regression of endometriotic lesions, complications can still arise during pregnancy and the peripartum period. Complications include the decidualization of endometriosis implants, with site-specific implications (e.g., decidualized endometrioma mimicking ovarian cancer, decidualized deep endometriosis infiltrating the myometrium leading to uterine rupture, spontaneous hemoperitoneum), placenta previa, preterm labor and premature rupture of membranes, postpartum hemorrhage, or systemic conditions such as hypertensive or coagulation disorders. Herein, we review the background of these conditions and the expected radiologic findings. Additionally, we review essential clinical concepts about the treatment available and the information needed to make health care decisions. This review aims to equip radiologists with essential insights into the challenges faced by patients with endometriosis, from infertility diagnosis through postpartum care. By enhancing radiologists’ understanding of these aspects and relevant imaging findings, we aspire to improve maternal and fetal outcomes affected by this complex condition.</p>