In order to get Point of Sale / USB Scanning devices to work properly with Windows Server 2008 R2 and higher, you must enable RemoteFX USB redirection on the user Windows devices using GPO. Please note that this policy setting allows you to permit RDP redirection of other supported RemoteFX USB devices from this computer. Make sure that you set RemoteFX USB Redirection Access Rights to Administrators and Users. This is configured by navigating to Computer Configurations > Administrative Templates > Windows Components > Remote Desktop Services > Remote Desktop Session Host > Remote Desktop Connection Client: