Carcinoma cuniculatum is an extremely rare and often indolent cancer that can mimic a benign process, such as osteomyelitis or odontogenic infections. This results in a definitive diagnosis that is delayed. To complicate the evaluation of this uncommon neoplasm, biopsies are often misinterpreted secondary to an incorrectly obtained tissue sample. Incisional biopsy needs to be done in a specific manner with a high degree of clinical suspicion incorporated into the patient assessment for the most accurate diagnosis. Local and distant failure rates are low with aggressive surgical resection and surgery upfront remains the treatment of choice when feasible. We present two cases that highlight the difficulty in accurate diagnosis and management of these rare cancers.