Cutaneous endometriosis (CEM) is a rare disease characterized by endometrial glands and/or stroma in the skin. Lesions present as a firm papule or nodule and can be blue, violaceous, red, brown or skin-colored. Patients frequently report cyclical tenderness, swelling and bleeding at the site of the lesion related to their menstrual cycle. CEM presents a diagnostic challenge as lesions are commonly mistaken for a keloid, dermatofibroma, dermatofibrosarcoma protuberans, melanoma or cutaneous metastasis of cancer (e.g., Sister Mary Joseph nodule). A biopsy must be taken to rule out malignancy and treatments include surgical excision and hormonal agents. To our knowledge, just over 100 cases have been reported in the literature. Herein we highlight a case of CEM in a 43-year-old female that presented to dermatology after being overlooked on prior work-up with obstetrics and gynecology. This case highlights the need for dermatologists to be familiar with CEM, as we may be the first clinicians these patients present to for painful cutaneous lesions.