Cutaneous melanoma remains an ongoing public health threat, and the cornerstone of management continues to be early diagnosis and treatment. Unfortunately, primary melanomas may have atypical presentations, making early diagnosis difficult and causing significant treatment delays. In this report, an unusual case is presented in which a patient experienced the synchronous development of a melanoma in situ within a skin graft donor site and an invasive melanoma within the recipient skin graft site. This exceptional presentation of cutaneous melanoma is discussed to highlight key principles of skin grafting in relation to the management of malignant melanoma.