The Neotropical genus Pentacalia Cass. (Compositae, Senecioneae) is distributed from southern Mexico to northwestern Argentina, plus two disjunct species that thrive in Brazil. Most species diversity occurs in the montane forests of Colombia, Ecuador, and Peru. It comprises scandent woody plants characterized by displaying alternate leaves (opposite in three species), involucres with supplementary bracts, usually yellow ray florets (when present), sagittate to caudate anther bases, and truncate to obtuse style branches with a crown of sweeping trichomes (sometimes with a tuft of longer trichomes, but not strictly penicillate). The Bolivian species were revised for the first time by Cabrera (1985), who treated the group under Senecio L. sect. Streptothamni Greenm. Because of the subsequent addition of new species and the need of taxonomic arrangements, an updated synopsis of the genus recognizing 18 species is presented. The names P. brittoniana (Hieron.) Cuatrec. and P. miguelii (Cuatrec.) Cuatrec. are synonymized with P. psidiifolia (Rusby) Cuatrec., as well as P. inquisiviensis H. Rob. & Cuatrec. with P. cardenasii (Cuatrec.) Cuatrec. and P. sailapatensis (Cuatrec.) Cuatrec. with P. urubambensis (Cabrera) Cuatrec. Seven names are lectotypified and an epitype is designated for the name P. zongoensis (Cabrera) J. Calvo. The new species P. viburnifolia J. Calvo & A. Fuentes is described. Revised nomenclature, succinct descriptions, taxonomic discussions, lists of specimens examined, and distribution maps are provided for all accepted species, in addition to an identification key. Pictures of living plants are also presented for eight species.