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I have the same problem than Bo, on a clean laptop with no previous install of EnergyPlus, OpenStudio nor Ruby. This is Windows Pro 10 21H1, 64-bit. I have admin privileges, and tried to run the exe as admin, as well as tried to execute the openstudio app from the zip file as admin. The error window is always the same, shown below. It is not clear which path the package is trying to access. I also tried first installing Energyplus 9.5.0 and Ruby 2.7.2 with devkit. Those installations go through just fine. Then, same error. Please advise. Thank you