The Parareptilia, the sister group to the Eureptilia, is poorly known, with many taxa in need of adequate description. One such taxon, Macroleter poezicus is found in Middle Permian strata of the Mezen River Basin in the Arkhangel'sk Province of Russia. The cranial anatomy of Macroleter is described from four new well-preserved specimens, and 89 cranial characters are incorporated into a phylogenetic analysis of parareptiles. A single most parsimonious topology is found, consisting of 205 steps, with the novel result that Macroleter is the taxon most closely related to pareiasaurs. This result has important implications for the phylogeny of the Parareptilia as well as for the identity of a disputed element (the tabular) in the skull of pareiasaurs.