Thank you for taking the time to work with me on this. It is greatly appreciated.
In the debug log I see SimpleService.exe as a service being killed with no whitelist line under it but it appears that file isn't actually the file that keeps the remote session active anyways.
I manually killed the SimpleService.exe service and the remote session stays active with no problems.
Please see screenshot link below for the correct file to whitelist (Java(TM) Platform SE binary (32-bit)