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Ectropion is a condition in which the lower eyelid turns outwards from the globe. It is commonly due to age related involutional laxity of the lid tissue. Ectropion may also be secondary to scarring or contracture of the periorbital skin and underlying tissues which pulls the eyelids outwards. Jessner’s lymphocytic infiltrate is a rare and enigmatic dermatological condition which is uncommon in the elderly. We describe a case of recurrent ectropion following redo lid surgery in which Jessner’s lymphocytic infiltrate was fortuitously diagnosed on skin biopsy. We are unaware of any report in the literature describing recurrent cicatrical ectropion due to this condition.