Cosmetic injection of hyaluronic acid (HA) and other fillers is increasingly common, and the late complications of these relatively new procedures are now coming to medical attention. Three patients with delayed periocular swelling that began years after injection of HA are described, with CT, MRI, and histopathologic characterization. While HA fillers are marketed as having a temporary effect of several months, the authors demonstrate that they may persist in the body for up to 9 years. Unlike most previous reports, there was no inflammatory reaction or encapsulation, simply infiltration into more superficial subcutaneous layers. All cases improved after surgical biopsy and hyaluronidase injections. Delayed periocular swelling after filler injections from several years prior can mimic serious medical conditions. With a detailed history and high index of suspicion, one may avoid a costly and invasive workup.