Dunno if this will help, it might not be the source of the issue. Try this at the CLI: `xattr -r -d com.apple.quarantine </path/to/file>` This is for app quar

Dunno if this will help, it might not be the source of the issue. Try this at the CLI: `xattr -r -d com.apple.quarantine </path/to/file>` This is for app quarantine (who'd guess) when apps are newly downloaded or unsigned. Look up the command for more info. There was some chatter here the other day (within the last week, I believe) about overcoming some bug or another that prevents MacOS from prompting when permissions are needed. The solution was modifying an SQLite db on disk. I don't believe the change is documented where the public can verify the whole thing, but I think at least one person verified that it worked for them after the OP. The OP (or replying party) sounded reasonably knowledgeable about why this would work, fwiw. I'd follow their steps if I had the same issue and I wouldn't be nervous. I think the second is more likely. Apparently, permissions in Sys Settings are pretty bad. I'm fortunate not to have had this affect me and my many devices that surely run that workflow.