Purpose: Follicular squamous cell carcinoma (SCC) is a rare variant of cutaneous SCC arising from the wall of a hair follicle. It is extremely rare with less than 100 cases reported in the current literature. It poses a diagnostic dilemma as it may be mistaken for metastatic SCC and can lead to unnecessary investigations and treatment. Methodology: We report a case of this rare condition. Results: An otherwise healthy 43-year-old male presented with a history of chronic sinus discharge from a cystic lesion of his right groin initially mistaken as an infected sebaceous cyst. He had no other history of malignancy and was a Fitzpatrick IV skin type. He underwent surgical excision of the cyst. Initial histopathology suggested a well differentiated SCC arising from an epidermoid cyst. Due to the unusual appearance, further examination of the histology revealed a primary well differentiated SCC arising from infundibular hair follicle epithelium. After focused examination for additional skin malignancies, he underwent further oncological excision of the previous scar. No further evidence of recurrence has been noted. Conclusion: This case highlights the importance of considering histopathology testing of surgically excised specimens even where clinical suspicion may be low. Follicular SCC is a rare variant of SCC that can be misdiagnosed. The histopathological appearance can be confused with metastatic SCC which can lead to further staging investigations and treatment which are unnecessary and pose a risk of treatment burden. Recommendations for management of follicular SCC are the same as standard SCC. Current literature suggests a positive prognosis with low risk of recurrence and metastases.