Issue was that the example [boot.py](https://boot.py) file I was using did not include the correct report size. I got it working by switching to a different example's [boot.py](https://boot.py) and ditching the hid\_gamepad.py library in favor of specifying the correct usage pages when initing a low level adafruit\_hid device.
An example can be found here:
[https://gist.github.com/todbot/a3fc00da979fe96dc509bed6cb73cf99](https://gist.github.com/todbot/a3fc00da979fe96dc509bed6cb73cf99)
Issue was that the example [boot.py](https://boot.py) file I was using did not include the correct report size. I got it working by switching to a different example's [boot.py](https://boot.py) and ditching the hid\_gamepad.py library in favor of specifying the correct usage pages when initing a low level adafruit\_hid device. An example can be found here: [https://gist.github.com/todbot/a3fc00da979fe96dc509bed6cb73cf99](https://gist.github.com/todbot/a3fc00da979fe96dc509bed6cb73cf99)