The authors present a case of seemingly textbook digital osteomyelitis with draining ulceration. Per protocol, specimens were sent to pathology with the intent to verify and identify the offending organisms. Surprisingly, the textbook osteomyelitis returned with a pathological diagnosis of rare sweat gland tumor, malignant eccrine acropsiroma, prompting immediate systemic medical workup and treatment. This case emphasizes the importance of proper laboratory workup of all surgically removed specimens, despite having a “typical” presentation. (J Am Podiatr Med Assoc 102(3): 247–251, 2012)