The halo nevus is characterized by a ring of depigmentation appearing around an acquired or congenital melanocytic nevus. When observed in children, halo nevi are generally not a cause of concern. However, adult-onset halo nevi have an associated risk of primary cutaneous melanoma that corresponds to the risk of melanoma in patients with atypical nevi or a personal/familial history of melanoma. Thus, new-onset halo nevi in adults requires close follow-up and monitoring for malignancy. Herein we present a case of an adult patient who received sequential digital dermoscopy, reflectance confocal microscopy, and pigmented lesion assay gene expression profiling to monitor two halo nevi over a three-month period.