Reinvestigation of the anatomically preserved stem Palaeosmunda plenasioides from the Lopingian (Late Permian) of China has led to the establishment of Zhongmingella gen. nov. within the extinct family Guaireaceae (Osmundales). Zhongmingella has a rhizomatous stem with heterogeneous pith and cortex comprising parenchyma and uniformly distributed secretory cells, and is dictyostelic. In order to evaluate the systematic and phylogenetic position of Zhongmingella within Guaireaceae, and Guaireaceae within Osmundales, we conducted a preliminary cladistic analysis of a broad range of Osmundales and related taxa based on 18 extinct and six extant genera and subgenera. Results do not support the traditionally deﬁned family Thamnopteroideae (Bathypteris, Chasmatopteris, Iegosigopteris, Thamnopteris, Zalesskya) and demonstrate that Thamnopteroideae is not a subfamily of Osmundaceae as previously thought. Guaireaceae is monophyletic but in addition to its traditionally deﬁned members (Guairea, Lunea, Donwellicaulis, Itopsidema, Shuichengella, Zhongmingella) includes the stratigraphically younger genus Osmundacaulis previously placed in Osmundaceae. Guaireaceae is sister to Osmundaceae, Millerocaulis, Ashicaulis, Palaeosmunda and Aurealcaulis in the strict consensus, but in the majority-rule consensus Palaeosmunda, Aurealcaulis, Ashicaulis and Millerocaulis formthe Osmundaceae stem group, with (Aurealcaulis, (Ashicaulis + Palaeosmunda)) sister to the extant genera. Stratigraphical analysis of the selected most parsimonious tree demonstrates that Osmundales underwent primary radiation during the Pennsylvanian and Permian, terminating abruptly around the time of the end-Permian mass extinction. Radiation within Osmundaceae occurred in the Triassic–Cretaceous and stratigraphically overlaps staggered extinctions in Guaireaceae and Osmundaceae from the Late Jurassic to mid-Cretaceous alongside the earliest angiosperm radiation. Our results identify the Osmundaceae stem and sister groups for the ﬁrst time, and represent an important step in unravelling the evolutionary history of Osmundales. However, reconstructed whole-plant species are imperative to improve understanding of the relationships within the clade in deep time.