could the processor on the Anywhere USB be too busy? I’ve seen something like that happen before. What happens if you disconnect a few ports. Does it still fail then?
Another thing you may want to review, is to ensure the ports and groups are configured correctly in the web interface in the RealPort USB section. Make sure you reboot the AW/14 for the new groups to take effect.
Have you tried a USB mouse or USB keyboard in that port to see if the USB port is working correctly?
Does the AnywhereUSB Viewer utility shows the proper USB devices connected?