The cumulus parameterization is widely recognised as a crucial factor in tropical meteorology: this paper intends to shed further light on the effects of convection parameterization on tropical cyclones’ numerical predictions in the “grey zone” (10–1 km grid spacing). Ten experiments are devised by combining five different convection treatments over the innermost, 5 km grid spacing, domain, and two different global circulation model datasets (IFS and ERA-Interim). All ten experiments are finally analysed and compared to observations provided by the National Hurricane Center’s best track record and multisatellite rainfall measurements. Results manifestly point to the superiority of employing no convective parameterization at the scale of 5 km versus the usage of any of those provided by WRF to reproduce the case study of Hurricane Tomas, which hit the Lesser Antilles and Greater Antilles in late October and early November 2010.