We report a micro-CT study of a new specimen of Dryolestes priscus (Dryolestidae, Cladotheria) from the Upper Jurassic Morrison Formation of Wyoming. The fossil (KUVP 134101) is an incomplete lower jaw preserving eight intact teeth, including two premolars (p3, p4) and six molars (m1–6), along with double-alveoli for m7 and a single alveolus for m8. Its preserved teeth and molar alveoli are consistent with the dental formula in more complete jaws of this species (i4.c1.p4.m8–m9). Here we have newly characterized diagnostic features on the molar trigonid of Dryolestes priscus and other species of Dryolestidae. Our analysis places this specimen close to Dryolestes priscus in terms of phylogeny. CT scans and visualization made it possible to illustrate the distinctive root structures of lower molars of dryolestid species. The two-rooted lower molars of D. priscus show a hypertrophied anterior root that is spatulate and much broader and longer than the simpler posterior root of the same molar. The disparate shape and size of the two molar roots are a highly derived pattern of dryolestids, which is absent in closely related genera formerly assigned to “paurodontids.” It is also unique among all mammaliaforms with typically two-rooted molars. The hypertrophied anterior root corresponds to most of the molar crown, and likely provided better support for occlusal forces acting on the large trigonid of the molar.