Detailed description of the Middle Permian Russian caseid Ennatosaurus tecton shows that three autapomorphies distinguish it from other caseids: a broad anterior ramus of the jugal, a large contribution of the frontal to the dorsal orbital margin, and a relatively narrow parasphenoid body. Phylogenetic analysis of Caseidae yields a single most parsimonious tree and its topology posits Ennatosaurus tecton as the sister taxon to the clade of the North American caseids Angelosaurus dolani and Cotylorhynchus romeri. Phylogenetic analysis supports the position of Oromycter dolesorum from the Lower Permian Richards Spur locality as the most basal member of Caseidae. In addition, the genus Casea is resolved as paraphyletic, whereby C. rutena forms the sister taxon to the clade containing E. tecton, C. romeri, and A. dolani. The current topology reveals that the pattern of dental complexity in terms of the number of apical cuspules is homoplasious, cautioning against its use as a unidirectional phylogenetic character.