The present study demonstrates the systematic optimization of a potential function against host-guest binding free energy data using an automatic and scalable workflow. This advance is made possible by our extension of the OpenFF-Evaluator software framework and curation of 126 host-guest complexes ready to be used in ABFE calculations. Our initial application involves the optimization of GB cavity radii in the OBC2 implicit solvent model, but the present technology can also be used to optimize force field parameters against binding data in the context of an explicit treatment of solvent.