This study evaluates the capability of eddy-permitting regional ocean models to reproduce the interocean exchange south of Africa. In this highly turbulent region, we show that the vertical structure of the horizontal flows need to be appropriately resolved to realistically advect thermocline water masses into the South Atlantic. Our results point out that a grid-spacing of 1/24 degrees on the horizontal and 50 m on the vertical homogeneously distributed are required to account for a correct transport of surface and subsurface water masses properties and their in-route transformation by mixing. Preliminary Lagrangian analyses highlight the primary role of the upper-ocean mesoscale eddies on water masses transport and fate, with a particular emphasis on Antarctic Intermediate Waters (AAIWs) dynamics and characteristics. We evaluate the numerical results against observations (AVISO data and Argo floats profiles). Modeled and observed eddies were examined in number, polarity, size, trajectory, and for their contribution to AAIW properties. A clear asymmetry, in number and radius, emerges between cyclones and anticyclones. The high-resolution simulation was the most energetic, with more abundant and smaller structures than those detected in AVISO. However, eddy statistics compare reasonably well in terms of mean pathways when restricted to Agulhas Rings, which are on average quasi-Gaussian in shape. Regionally, the Ertel potential vorticity anomaly is marked at the surface by a temporal variability with winter intensification, directly reflected in the seasonal cycle of the eddies number. Noting the growth of the baroclinic Rossby radius in winter, this suggests baroclinic processes as essential for these eddies generation.