Excoriation or skin picking disorder is described as compulsive picking of the skin that cannot be explained by an underlying dermatological condition. There are unfortunately no clear guidelines in the literature for reconstruction of wounds in this patient population. The authors describe the cases of 2 patients with the skin picking disorder who underwent free flap reconstruction for scalp wounds, which were complicated by wound recurrence due to manipulation of the surgical site. The literature is reviewed in detail, and steps to potentially prevent recurrence in this patient population are discussed.