It looks like this is a Sony driver issue. Sometime around the 4.10 Linux kernel, the hid-sony.ko driver was updated and broke some USB Playstation adapters. Kernel v5.6.17 and up appear to fix it.
Relevant links:
The fix - https://lkml.org/lkml/2020/5/13/1323
Discussion and workarounds - https://www.linuxquestions.org/questions/linux-games-33/playstation2-controller-with-usb-adapter-need-help-getting-additional-buttons-to-work-4175643583/