We report the rare occurrence of a small bowel perforation secondary to a metastatic cutaneous squamous cell carcinoma (cSCC). A 70-year-old woman, who had previously undergone renal transplantation, presented with severe, sudden-onset abdominal pain. She was peritonitic on initial examination, with evidence of free intra-abdominal air on radiographic imaging. During an exploratory laparotomy, she was found to have a perforated jejunum secondary to disseminated metastases seen throughout her peritoneum. Following histopathological analysis, as well as further imaging studies, the primary malignancy was eventually identified as a cSCC on her upper back. Palliative care was started and the patient died 8 weeks following her initial presentation.