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Abstract We compute the soft-drop jet-mass distribution from pp collisions to NNLL accuracy while including nonperturbative corrections through a field-theory based formalism. Using these calculations, we assess the theoretical uncertainties on an α s precision measurement due to higher order perturbative effects, nonperturbative corrections, and PDF uncertainty. We identify which soft-drop parameters are well-suited for measuring α s , and find that higher-logarithmic resummation has a qualitatively important effect on the shape of the jet-mass distribution. We find that quark jets and gluon jets have similar sensitivity to α s , and emphasize that experimentally distinguishing quark and gluon jets is not required for an α s measurement. We conclude that measuring α s to the 10% level is feasible now, and with improvements in theory a 5% level measurement is possible. Getting down to the 1% level to be competitive with other state-of-the-art measurements will be challenging.