Starting in E:, I never experienced an issue in all my testing. I tried leaving the 'Start in' as the system32 folder, then using the shortcut of 'runas.exe /user:\Administrator /savecred E:\Unlock.exe', but for some reason it would not consistently work. Once I created the shortcut, because the external drive mounts as E: (where the decryption tool is stored), I right-clicked the shortcut I had just created and set the 'Start in' as E. I would have used domain temp admin account, but because it is a laptop and the user will be traveling, I wanted to be 100% positive it would work anywhere he used his computer. Be sure to password protect the local admin account and enable it beforehand. The destination of the shortcut was 'C:\Windows\System32\runas.exe /user:\Administrator /savecred Unlock.exe' The steps are listed below, in case anybody else is trying to find the solution I used to solve this problem. I was finally able to solve my problem by creating a shortcut. I tried right-clicking on the exe and telling it to run as Admin, then save the credentials, and it did not keep those settings. I looked further in to the issue, and I realized Power Users are only listed as an option for backwards compatibility in Windows 7.