The collapse of late Permian (Lopingian) Gondwanan floras, characterized by the extinction of glossopterid gymnosperms, heralded the end of one of the most enduring and extensive biomes in Earth’s history. The Sydney Basin, Australia, hosts a near-continuous, age-constrained succession of high southern paleolatitude (∼65–75°S) terrestrial strata spanning the end-Permian extinction (EPE) interval. Sedimentological, stable carbon isotopic, palynological, and macrofloral data were collected from two cored coal-exploration wells and correlated. Six palynostratigraphic zones, supported by ordination analyses, were identified within the uppermost Permian to Lower Triassic succession, corresponding to discrete vegetation stages before, during, and after the EPE interval. Collapse of the glossopterid biome marked the onset of the terrestrial EPE and may have significantly predated the marine mass extinctions and conodont-defined Permian–Triassic Boundary. Apart from extinction of the dominant Permian plant taxa, the EPE was characterized by a reduction in primary productivity, and the immediate aftermath was marked by high abundances of opportunistic fungi, algae, and ferns. This transition is coeval with the onset of a gradual global decrease in δ13Corg and the primary extrusive phase of Siberian Traps Large Igneous Province magmatism. The dominant gymnosperm groups of the Gondwanan Mesozoic (peltasperms, conifers, and corystosperms) all appeared soon after the collapse but remained rare throughout the immediate post-EPE succession. Faltering recovery was due to a succession of rapid and severe climatic stressors until at least the late Early Triassic. Immediately prior to the Smithian–Spathian boundary (ca. 249 Ma), indices of increased weathering, thick redbeds, and abundant pleuromeian lycophytes likely signify marked climate change and intensification of the Gondwanan monsoon climate system. This is the first record of the Smithian–Spathian floral overturn event in high southern latitudes.