Does the same thing happen if you unlock your login keychain in the Keychain application in Utilities?
It might just need access to the keychain to get permission, through some accessibility service, to be able to use the remapped buttons. I’d guess that there’s no link to force / ask the keychain to unlock and allow it as the Logitech software is older than the new permissions process.
This is very alarming. I have a razor mouse and it also occasionally stops doing the macros. Most frequently after resume/return from lock
If it happens I'll try using this cool fix! /s
Wow, that sounds like something rather dangerous and underhanded is going on.