Convective initiation and growth are sensitive to atmospheric conditions, especially humidity, in ways that need to be understood and quantified. It is not clear, however, how well current observations and modelling systems can serve to test this understanding. We simulate multiple cases of convergent cloud lines observed during January 2016 over northeastern Australia using the Weather Research and Forecasting (WRF) model (version 3.7.1), initialized by and nudged to reanalysis data. Overall, WRF appears to skilfully simulate the convergence lines. However, the associated convective clouds as seen by satellite were not properly captured by the model. The model humidity was tested against the current version (V3‐00) of the Megha‐Tropiques satellite, which although up to 30% too moist in the lowest retrieved layer over the dry continental interior compared to radiosondes, is usually accurate to within ±10% near the cloud lines. Unperturbed WRF simulations were found to be 10–20% too dry in this region. Compensating for this humidity bias via the model initialization produced more realistic simulations of clouds and convection, and this had a comparable or larger impact than changing model physics. This result highlights the importance of observations of water vapour that are accurate and have good spatial coverage, especially in the lower troposphere, for properly constraining simulations of convective environments and for model evaluation of moist processes.