The gasteroid genus Richoniella and the cyphelloid genus Rhodocybella (Entolomataceae) are poorly known fungal genera that have yet to be evaluated in depth in a molecular phylogenetic context. Here, we report a recent find, including detailed descriptions and photographs, of the rarely collected gasteroid species Richoniella asterospora from southeast North America. Phylogenetic placement of this species within a multi-gene treatment of the Entolomataceae supports the polyphyly of Richoniella. Richoniella asterospora shares an alliance with agaricoid and secotioid species within the diverse, heteromorphic genus Entoloma. Also rarely encountered is the cyphelloid genus Rhodocybella, known only from southeast North America. Molecular annotation and phylogenetic analysis of the holotype suggest an affiliation with two lignicolous European pileate-stipitate species of Entoloma, E. pluteisimilis and E. zuccherellii. Results from molecular annotation of three additional species of Entolomataceae are also reported. In addition, we propose recognition of the following robust monophyletic groups: the Pouzarella clade within the genus Entoloma; and the genera Rhodocybe and Clitopilopsis and the Rhodophana clade, apart from the genus Clitopilus, within which they have been recently subsumed. Both Richoniella asterospora and Rhodocybella rhododendri are transferred to the genus Entoloma to maintain its monophyly.