Keyboard shortcuts sometimes require several restarts before they work

[caffeinated2]

I'm running budgie 19.10 on a laptop with an OLED screen. As such, the brightness buttons don't work (my understanding is that they adjust a backlight knob which is ignored by OLED displays). As a workaround I found I could use xrandr to adjust brightness levels, so now I have a bash script that emulates brightness reset, up, and down. I've tried using the keyboard shortcuts from settings->devices->keyboard to map key presses to execute this bash script.

I've found that these shortcuts work sometimes. Sometimes when I boot and login the new shortcuts do nothing, but system shortcuts (e.g. ctrl-alt-t) work as expected. I have to restart my laptop enough times (5x is my current record) before my shortcuts work.

I don't know how to begin to troubleshoot this, any advice is appreciated.