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Actinic cheilitis is a chronic inflammatory disorder of the lip, affecting the lower lip mainly, caused by cumulative long-term effects of ultraviolet (UV) radiation in sunlight. It is a premalignant condition with a malignancy potential of 6-10%. It is reported that it almost exclusively occurs in fair-skinned people and those who work outdoors. However, it has recently been reported that actinic cheilitis is not exclusive to fair-skinned people. It is most common in middle-aged or older male patients. Diagnosis of actinic cheilitis is mainly based on demographical, clinical, and histopathological findings. Factors such as socioeconomic status, smoking, dietary habits, and genetic predisposition are also associated with lip cancer. Here, we present a case of actinic cheilitis in two siblings and in their mother, showing a familial pattern. An incisional biopsy of the lower lip in the mother showed severe dysplastic changes indicating transformation to squamous cell carcinoma.