Inverted papilloma is a rare benign neoplasm that usually originates in the lateral nasal wall. It can be a locally aggressive lesion and invade nearby structures. While primarily a nasal neoplasm, cases of an inverted papilloma involving the temporal bone, pharynx, nasopharynx, and lacrimal sac have been reported. We describe the case of a 67-year-old man with a history of nasal inverted papilloma who presented with a recurrent nasal mass and a large mass on the left side of his upper neck. The patient's history included inverted papillomas in multiple locations: the temporal bone, the sinonasal tract, and the nasopharynx. The new neck mass raised a concern for malignant degeneration and metastasis, but pathology demonstrated that it was a benign inverted papilloma. No clear etiology for the new neck lesion was evident except for an origin in salivary gland tissue. However, there was no physical connection between the neck mass and the submandibular gland identifiable on pathologic evaluation. This case illustrates the need for an aggressive primary resection to minimize local recurrence, as well as adequate surveillance to address recurrences early. Given the potential for multicentricity, patients with a typical sinonasal inverted papilloma should undergo a complete head and neck examination as part of their follow-up.