i’ll get back to you if i can figure out how to trigger the prompt again

I think this only shows once. If you say no it will just deny the next requests automatically. Not sure how to reset though. I'll try this too.

Was it along the tests running?

This will also only happen from applications running with a GUI, when osquery is running as a launchdaemon this fails silently.

Is that on Mojave? I think that’s because of the new TCC profile. I think you can reset it by going to System Preferences -> Security & Privacy -> Privacy, and removing the entry there