Prolapse of the lacrimal gland is an acquired clinical condition caused mainly by relaxation of the local suspending ligaments. Before an aesthetic blepharoplasty, there should be a preoperative clinical suspicion of lacrimal gland pathology for patients with bulging lateral thirds of the upper eyelids. It should be borne in mind that inadvertent removal of the lacrimal gland can lead to important alterations in ocular lubrication. This report describes two clinical cases of patients with lacrimal gland prolapse associated with dermatochalasis and their treatment.