Calculator not detected

[mcGLITCHGUITAR]

I have tried multiple different sequences of running the apps, but I cannot get the windows app to detect my calculator. If the ti84 app isn't running, it does see it and also tells me that calc2key is not running. I updated everything (even the operating system). Does this work on jailbroken calculators?
P.S. I am reasonably versed in computers and may be able to give you more info if I know what to look for.