Cutaneous squamous cell carcinoma (cSCC) is a common malignancy in the head and neck region. Although rarely metastatic, it has the potential to become locally aggressive and invade surrounding structures. The involvement of the scalp with cSCC presents a unique surgical challenge given its proximity to vital structures. We present a case of locally advanced cutaneous scalp squamous cell carcinoma with involvement of the skull and dural involvement not previously demonstrated on imaging. This case required complex multidisciplinary surgical management from both neurosurgery and head and neck surgery for treatment, preservation of essential tissues, and cosmesis.