Cancers of the perionychium are relatively rare occurrences and are often related to chronic inflammation associated with trauma, infection, exposure to ultraviolet radiation, or other carcinogens. Squamous cell carcinoma is the most common tumor reported of the nail bed. Synchronous squamous cell carcinomas of the perionychium have been rarely reported. We present a case of a 46-year-old woman with synchronous squamous cell carcinomas involving both hands and multiple digits. Treatment modalities include chemotherapeutics, Mohs surgery, and amputation. Early diagnosis of squamous cell carcinoma of the nail bed provides the greatest chance to preserve maximal function of the hand. Onychomycosis may be the presenting symptom of a patient with squamous cell carcinoma and may also be a predisposing factor in patients with occupational risk factors. Suspicion of this disease process can help the clinician establish the diagnosis via biopsy and provide optimal care for these patients.