In late March 2014, very intense Tropical Cyclone Hellen threatened the Comoros Archipelago and the Madagascan northwest coastline as it became one of the strongest tropical cyclones (TCs) ever observed over the Mozambique Channel. Its steep intensity changes were not well anticipated by operational forecasting models or by La Reunion regional specialized meteorological center forecasters. In particular, the record-setting rapid weakening over the open ocean was not supported by usual large-scale predictors. AROME, a new nonhydrostatic finescale model, is able to closely reproduce these wide intensity changes. When benchmarked against available observations, the model is also consistent in terms of inner-core structure, environmental features, track, and intensity. In the simulation, a northwesterly 400-hPa environmental wind is associated with unsaturated air, while the classic 200-850-hPa wind shear remains weak, and does not suggest a specifically unfavorable environment. The 400-hPa constraint affects the simulated storm through two pathways. Air with low equivalent potential temperature (u e) is flushed downward into the inflow layer in the upshear semicircle, triggering the decay of the storm. Then, direct erosion of the upper half of the warm core efficiently increases the surface pressure and also plays an instrumental role in the rapid weakening. When the storm gets closer to the Madagascan coastline, low-u e air can be directly advected within the inflow layer. Results illustrate on a real TC case the recently proposed paradigm for TC intensity modification under vertical wind shear and highlight the need for innovative tools to assess the impact of wind shear at all vertical levels.