The Eocene–Oligocene transition (EOT) is marked by a sudden δ18O excursion occurring in two distinct phases approximately 500 kyr apart. These phases signal a shift from the warm middle to late Eocene greenhouse climate to cooler conditions, with global surface air temperatures decreasing by 3–5 °C and the emergence of the first continent-wide Antarctic ice sheet (AIS). While ice sheet modelling suggests that ice sheet growth can be triggered by declining pCO2, it remains unclear how this transition was initiated, particularly the first growth phase that appears to be related to oceanic and atmospheric cooling rather than ice sheet growth. Recent climate model simulations of the late Eocene show improved accuracy but depict climatic conditions that are not conducive to the survival of incipient ice sheets throughout the summer season. This study therefore examines whether it is plausible to develop ice sheets of sufficient scale to trigger the feedback mechanisms required to disrupt the atmospheric regime above the Antarctic continent during warm and moist late Eocene summers and establish more favourable conditions for ice expansion. We aim to assess the sustainability of an incipient AIS under varying radiative, orbital and cryospheric forcing. To do so, we evaluate Community Earth System Model 1.0.5 simulations, using a 38 Ma geographical and topographical reconstruction, considering different radiative and orbital forcings. The climatic conditions prevailing during (and leading up to) the EOT can be characterised as extremely seasonal and monsoon-like, featuring a short yet intense summer period and contrasting cold winters. A narrow convergence zone with moist convection around the region with high sub-cloud equivalent potential temperature exhibits a ring-like structure, advecting moist surface air from the Southern Ocean in both summer and winter. This advection leads to high values of moist static energy and subsequent precipitation in coastal regions. Paradoxically, this atmospheric regime – particularly its coastal precipitation in winter – appears to be necessary for the sustenance of the moderately sized regional ice sheets we imposed on the continent, contrary to our assumption that these ice sheets would disrupt the atmospheric regime. This underscores a hysteresis effect for regional ice sheets on the Antarctic continent, suggesting the potential for a significant volume of ice on the continent without imminent full glaciation prior to the EOT.