The sensitivity of the October 1996 medicane in the western Mediterranean basin to sea surface temperatures (SSTs) is investigated via 24-member ensembles of regional climate model simulations. Eleven ensembles are created by uniformly changing SSTs in a range of −4 K to +6 K from the observed field, with a 1 K step. By using a modified phase space diagram and a simple compositing method, it is shown that the SST state has a minor influence on the tracks of the cyclones, but a strong influence on their intensities. Increased SSTs lead to greater probabilities of tropical transitions, to stronger low- and upper-level warm cores, and to lower pressure minima. The tropical transition occurs sooner and lasts longer, which enables a greater number of transitioning cyclones to survive landfall over Sardinia and to re-intensify in the Tyrrhenian Sea. The results demonstrate that SSTs influence the intensity of fluxes from the sea, which leads to greater convective activity before the storms reach their maturity. These results suggest that the processes at steady-state for medicanes are very similar to tropical cyclones.