The phylogenetic integrity and relationships of the pleurocarpous moss Hypnodendron and several potentially related taxa are investigated using chloroplast rbcL, trnL-F, and rps4 sequence data, the mitochondrial nad5 region, and a set of 29 morphological characters. Strong support is obtained for the recognition of a monophyletic group, the “hypnodendroid pleurocarps,” that includes Hypnodendron, Braithwaitea, Pterobryella praenitens, the Cyrtopodaceae, Spiridentaceae, and Racopilaceae. This clade is resolved as sister to the Hypnanae with moderately strong support. Hypnodendron is paraphyletic, with H. section Sciadocladus resolved as sister to Pterobryella praenitens and outside of a very well supported clade that includes the other taxa of Hypnodendron in addition to the Spiridentaceae and Cyrtopodaceae. Chloroplast and mitochondrial sequence data show a high degree of congruence, and confidence in critical nodes is increased by long branches, high support values, and indels corresponding to radical modification of sequence and secondary structure within the nad5 group I intron. Based on morphological character state optimisation the hypnodendroid pleurocarps comprise a clade that includes plesiomorphically dendroid, palmate/umbellate terrestrial plants in addition to a number of derived lineages representing adaptive shifts towards epiphytism. These include the prostrate/creeping Racopilaceae, the dendroid-pinnate species in Hypnodendron section Phoenicobryum, and the simple, large-leaved Spiridentaceae and Cyrtopodaceae. Our data also support recognition of the hypnodendroid pleurocarps at the ordinal or superordinal level.