Fine-tuning criteria are frequently used to place upper limits on the masses of superpartners in supersymmetric extensions of the standard model. However, commonly used prescriptions for quantifying naturalness have some important shortcomings. Motivated by this, we propose new criteria for quantifying fine tuning that can be used to place upper limits on superpartner masses with greater fidelity. In addition, our analysis attempts to make explicit the assumptions implicit in quantifications of naturalness. We apply our criteria to the minimal supersymmetric extension of the standard model, and we find that the scale of supersymmetry breaking can be larger than previous methods indicate.