Intravascular papillary endothelial hyperplasia (IPEH), often referred to as Masson’s Tumor, is an uncommon yet benign vascular disease of the skin and subcutaneous tissues. It usually arises within a blood vessel, but is considered to be a non-neoplastic reactive endothelial proliferation commonly associated with vascular injury. Although it is rare, knowledge of this disease is important as it may mimic other benign and malignant tumors, especially angiosarcoma, which may lead to unnecessary aggressive management. Typically, IPEHs are asymptomatic and are slow growing soft-tissue masses with extremely low-recurrence rates. In this article, we describe a 19-year-old male with a recurrence of Masson’s Tumor over the right little finger within 2 months of a routine excision of the lesion. We also present accompanying multimodality clinical, radiological, and pathological imaging. This case illustrates the innocuous nature of the initial lesion easily mistaken for a hemangioma. Awareness of the possibility of a recurrence of a Masson’s Tumor is important for clinicians to rule out the presence of malignant vascular lesions.