Understanding momentum exchange at the air-sea interface is important for accurate hurricane predictions and understanding fundamental storm dynamics. One method for estimating air-sea momentum transfer in high winds is the flux-profile method, which infers surface momentum fluxes and the corresponding drag coefficient from mean velocity profiles obtained from either dropsondes or meteorological towers, under the assumption that the boundary-layer wind profile at low altitudes exhibits a logarithmic profile with height. In this study, we use dropsonde data from reconnaissance aircraft, as well as “virtual sondes” from a turbulence-resolving simulation of an intense tropical cyclone, to critically analyze the diagnosis of drag coefficient CD at hurricane-force wind speeds. In particular, the “roll-off” of the drag coefficient, where CD decreases at 10-m wind speeds ¿ 35 m s−1, is called into question based on uncertainty due to relatively low sample size and a lack of robustness of the flux-profile at high winds. In addition, multiple factors appear to favor an underestimate of CD at hurricane-force winds relative to their true values, including uncertainty in the height of recorded dropsonde data, violation of Monin-Obukhov similarity theory near the eyewall, and the short vertical extent of the logarithmic layer. Due to these and other related sources of uncertainty, it is likely that a quantitative limit has been reached in inferring the specific values of u* and CD using the flux-profile method, while at the same time the potential for underestimation may cast doubt on the CD–U10 relationship inferred from this method at high winds.