Autoimmune progesterone dermatitis (AIPD) is an uncommon condition in which allergic dermatitis to endogenous progesterone manifests in cyclic cutaneous eruptions. In this case series, we present 3 patients with AIPD, each with unique presentations and medical histories emblematic of the disease. Cyclic dermatitis related to menses in a premenopausal woman should raise high clinical suspicion for AIPD, especially in the primary care or emergency setting. Because of the rarity of this disorder, this case series seeks to describe AIPD to medical providers of young women, as well as present relevant literature related to the disease. We propose clinical considerations for women of reproductive age with AIPD.