I uninstalled all my drivers and reinstalled the ones you linked. When I plugged the STM board back in, Windows failed to install/find the right drivers. However OpenOCD found the ST-Link device. When it prompted for the WinUSB driver, I clicked “no” and it failed with the same error as before. If I click “OK” and install the winusb it still fails same as always. Tried using the driver tool to install the libusb-winusb driver over it, still fails.
The problem may be that the STM32 F103RBT6 I’m using has ST-Link v2.1, perhaps OpenOCD can’t handle that newer protocol. I can’t find any documentation of which ST-Link version the F103RB uses, so I’m not sure. But either way it’s killing me not to be able to debug my program.