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Since your are working on Windows Server, I'm guessing you probably have User Access Control turned on.
This prevents you or an application from accessing directories and executing programs.
If possible try turning UAC off and restarting the server to enable the change or start Change Assistant As Administror (using the right mouse button).
I think this should solve your issue.
Yes that makes absolute sense, however it did not work.
Strangely, and I hope just a little bit that it was only a crazy coincidence of some sort, what resolved the issue was editing the PATH environment variable. Which in itself is not surprising, what was curious was that the the PS_HOME\bin\client\winx86 directory had to be at the very beginning, before the first separator. When I reordered the PATH locations, Change Assistant miraculously started working :-)
When I get a chance I plan to do a bit more testing with this and try to report back.