A 41-year-old woman presented with pyoderma gangrenosum involving the right eyelids. Over the course of 3 years, she developed progressive scarring of the eyelids with lagophthalmos and corneal exposure. Multiple reconstructive procedures were performed with varying degrees of success. Despite aggressive medical control of her disease, it recurred in grafted skin on her upper and lower eyelids as confirmed by tissue biopsy. Periocular pyoderma gangrenosum is a rare disease where the management may be complicated by disease recurrence in reconstructed tissues, including skin grafts as this case demonstrates.