A 39-year-old female with no prior cancer diagnosis presented with a right breast lump that increased in pain with menstruation over the past 4 years. Imaging demonstrated two masses in the right breast and one mass in the left breast and image-guided core needle biopsy was consistent with bilateral granular cell tumors (GCTs) of the breasts. Based on the multifocal nature of the patient's breast masses and associated pain, diagnosis of GCT did not clinically correlate with the patient's presentation. However initial pathology on core biopsy showing positive staining for S100 and CD68, classic for GCTs, guided our treatment of this patient. Our patient was managed surgically with excisional biopsy yielding two masses in the right breast and one mass in the left breast. Final pathology confirmed the initial diagnosis of GCTs of the breasts, and the patient has had an uncomplicated postoperative course. Although GCTs of the breast typically present as solitary and painless masses, multifocal presentation and pain are possible. It is also important to rule out malignancy with excisional biopsy of the masses and take into account the possibility of upstaging. Furthermore, it may be warranted to explore underlying genetic conditions such as LEOPARD syndrome if patient presents with additional findings.