The discovery of a 125 GeV SM-like Higgs boson along with the absence of additional new physics signals have reinvigorated studies of "simple" supersymmetry breaking sectors. One such paradigm relies on anomaly plus gravity mediation; this model favors 3 TeV wino dark matter and gluinos in the O(10 TeV) range. Given these large masses, this model is difficult to test. In this talk, we will review the status of this scenario, followed by a description of two concrete experimental probes. An existing search for line photons emanating from the center of the galaxy will be used to challenge the wino dark matter hypothesis. Estimates for the reach of a future 100 TeV proton collider will be shown. This will demonstrate the potential to probe much of the interesting parameter space using human buildable technology.