Atypical and anomalous melanocytic lesions are tumors that cannot be determined by microscopy to be certainly benign or fully malignant. The malignant potential of these borderline lesions is unknown and logical determination of best therapy is challenging, in particular whether lymphatic mapping and sentinel node biopsy have a place in their management. Lesions that fall into this category include atypical Spitzoid lesions, atypical cellular blue nevi, combined nevi, deep penetrating nevi, ancient nevi, desmoplastic nevi, balloon cell nevi and proliferation nodules of congenital nevi. We report our experience managing patients with these problematic tumors and discuss our approaches to determining the true location of lesional cells in sentinel nodes.