Spiders in the genus Cybaeus L. Koch (Araneae : Dictynoidea : Cybaeidae) are common forest-floor inhabitants in western North America and Japan. Here we establish an initial phylogenetic framework for North American Cybaeus. Morphological details for eight proposed species groups are given, and these results, combined with molecular analyses of one nuclear and one mitochondrial gene for six of the eight species groups, suggest that North American Cybaeus species are contained in two broad clades, one Holarctic and one Nearctic (primarily Californian). The Holarctic clade contains the tetricus and angustiarum species groups, which contain mostly widely distributed species. The Californian clade includes the adenes, aspenicolens, consocius, devius, septatus and tardatus species groups, all of which have very restricted ranges. The genus Cybaeus and the Palaearctic species C. tetricus (C.L. Koch) (type species of the genus) and C. angustiarum L. Koch are redescribed and illustrated. A key to species groups is provided. Nine new species endemic to the western Nearctic and included in the molecular analyses are described and illustrated: C. paralypropriapus Bennett, sp. nov. and C. waynei Bennett, sp. nov. (tetricus group); C. sanbruno Bennett, sp. nov. (adenes group); C. thermydrinos Bennett, sp. nov. (aspenicolens group); C. penedentatus Bennett, sp. nov. and C. vulpinus Bennett, sp. nov. (consocius group); C. chauliodous Bennett, sp. nov. and C. somesbar Bennett, sp. nov. (septatus group); and C. gidneyi Bennett, sp. nov. (unplaced).