Suppressing naturalness concerns, we discuss the compatibility requirements of high-scale supersymmetry breaking with the Higgs boson mass constraint and gauge coupling unification. We find that to accommodate superpartner masses significantly greater than the electroweak scale, one must introduce large nondegeneracy factors. These factors are enumerated for the Minimal Supersymmetric Standard Model, and implications for the allowed forms of supersymmetry breaking are discussed. We find that superpartner masses of arbitrarily high values are allowed for suitable values of tan β and the nondegeneracy factors. We also compute the large, but viable, threshold corrections that would be necessary at the unification scale for exact gauge coupling unification. Whether or not high-scale supersymmetry can be realized in this context is highly sensitive to the precise value of the top quark Yukawa coupling, highlighting the importance of future improvements in the top quark mass measurement.