Experimental measurements of gas-phase acidities are quoted with uncertainties exceeding 2 kcal mol -1 (though most of that uncertainty is systematic, arising from the need to anchor the gas-phase acidity scale). Although gas-phase acidities can be predicted with relatively high accuracy using quantum chemical methods, such techniques are computationally expensive, limiting the feasibility of high-throughput workflows. To this end, an optimal balance between computational cost and accuracy is thus crucial for predicting gasphase acidities.