So I've narrowed it down to Catalina (10.15.1) not playing nice with parallels and my attached COBB Accessport USB device when I'm using Windows 10 in a VM window.
I can boot into boot camp (windows 10) just fine, connect to this device, use it, and disconnect as intended. Works just fine!
Parallels does not know how to handle the device when Windows is in a VM window, it's intermittent. It'll see the device *1 time*, connect to it and allow me to manage it. The second I eject it and try to connect to it again it won't connect until I reboot the windows VM. Then rinse and repeat.
I will also mention that the device is seen under "devices". It doesn't disappear from there. It is checked under that drop down and should be working, it just doesn't connect. Windows device manager sees it, just doesn't do anything with it.
I can boot into boot camp (windows 10) just fine, connect to this device, use it, and disconnect as intended. Works just fine!
Parallels does not know how to handle the device when Windows is in a VM window, it's intermittent. It'll see the device *1 time*, connect to it and allow me to manage it. The second I eject it and try to connect to it again it won't connect until I reboot the windows VM. Then rinse and repeat.
I will also mention that the device is seen under "devices". It doesn't disappear from there. It is checked under that drop down and should be working, it just doesn't connect. Windows device manager sees it, just doesn't do anything with it.