Background: Pleomorphic adenoma is the most common benign salivary gland neoplasm, characterized by its biphasic epithelial and myoepithelial components within a chondromyxoid stroma. Extensive squamous metaplasia in pleomorphic adenoma is uncommon and may create significant diagnostic challenges in fine needle aspiration cytology (FNAC), often mimicking malignant lesions such as mucoepidermoid carcinoma or squamous cell carcinoma. Case Presentation: We report a case of a 40-year-old man who presented with a slowly enlarging, painless mass in the right submandibular region for one year. Clinical examination revealed a well-circumscribed, mobile lesion with firm consintency. Ultrasonography examination showed an encapsulated mass with regular border with cystic and solid component suggestive for pleomorphic adenoma. FNAC showed abundant squamous cells arranged in sheets and clusters, with keratinous debris and epithelial cells, while the typical chondromyxoid stromal component was scant. These findings initially raised suspicion for a malignant salivary gland neoplasm, particularly mucoepidermoid carcinoma. Superficial parotidectomy was performed, and histopathological examination demonstrated a well-encapsulated pleomorphic adenoma with extensive squamous metaplasia and keratin cyst formation, without evidence of malignancy. Cyto-histopathological correlation confirmed the benign nature of the lesion. Conclusion: Pleomorphic adenoma with extensive squamous metaplasia is a rare diagnostic pitfall in salivary gland cytology. Awareness of this unusual presentation and careful search for subtle biphasic features are essential to avoid overdiagnosis and inappropriate aggressive management.