Cutaneous Squamous Cell Carcinoma (cSCC) is a rapidly growing tumour arising in the keratinocytes of the epidermis and is the most common skin cancer among African Americans and Asian Indians. We present the case of a 61-year-old Afro- Caribbean man who was referred to the Diabetic Foot Clinic with concerns about a superficial non-healing ulcer to the lateral aspect of the left foot of a 6-year duration. The patient reported autoamputation of the fifth digit at the time of presentation to our clinic. Over the previous years, he had been seen twice in primary care, and three times in secondary care services. Shortly after clinic review, he underwent incisional biopsy due to suspicion of Pyoderma gangrenosum, this showed an invasive squamous cell carcinoma. CT imaging was negative for metastatic visceral or nodal spread. Subsequently, he underwent amputation to the level of the ankle joint and analysis of intraoperative specimens confirmed poorly differentiated squamous cell carcinoma with infiltration of the skeletal muscle and bony tissue planes. The primary aim of this case report is to highlight the possibility of autoamputation due to invasive cSCC and the importance of biopsy in the case of non-healing and atypical ulcerative skin lesions.