Forecasts of tropical cyclone (TC) tornadoes are less skillful than their non‐TC counterparts at all lead times. The development of a convection‐allowing regional ensemble, known as the Warn‐on‐Forecast System (WoFS), may help improve short‐fused TC tornado forecasts. As a first step, this study investigates the fidelity of convective‐scale kinematic and thermodynamic environments to a preliminary set of soundings from WoFS forecasts for comparison with radiosondes for selected 2020 landfalling TCs. Our study shows reasonable agreement between TC convective‐scale kinematic environments in WoFS versus observed soundings at all forecast lead times. Nonetheless, WoFS is biased toward weaker than observed TC‐relative radial winds, and stronger than observed near‐surface tangential winds with weaker winds aloft, during the forecast. Analysis of storm‐relative helicity (SRH) shows that WoFS underestimates extreme observed values. Convective‐scale thermodynamic environments are well simulated for both temperature and dewpoint at all lead times. However, WoFS is biased moister with steeper lapse rates compared to observations during the forecast. Both CAPE and, to a lesser extent, 0–3‐km CAPE distributions are narrower in WoFS than in radiosondes, with an underestimation of higher CAPE values. Together, these results suggest that WoFS may have utility for forecasting convective‐scale environments in landfalling TCs with lead times of several hours.