What path did you choose to install the GP web client? Did you use the default location in the GP Web Client installer, or did you pick a different path? When a new session is created, some data is written to a session folder that is located inside of the GP Web client installation location you specified. If this path is too long (greater than 255 characters, if I recall correctly) then the files can't be created. If that's the case, then you need to install the web client into a location with a shorter path.
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