How aware? Do they have any vision? Can they "see" or otherwise "know" about the cutters / workholding?
AFAIK the crash guard is a separate component that relies on 3d models of the machine and the tools, it doesn't see anything.
If you workholding is weak and a piece comes loose the crash guard probably won't make a difference.
Tool configuration is kinda-sorta solved with ISO 13399, this is being supported in more and more CAM systems and tool vendors, but as you say it is very easy to make a mistake.
Assuming the mistakes are happening when the tool data is reduced from the comprehensive format that ISO 13399 supports to the barebones and simple TxDxHx format that is loaded on CNC machine. Would be nice if machine tools supported a comprehensive format directly.
Certainly a chicken and egg problem though, my ideal future would have CAD files generated from single source of truth CNC files:)
If the supports/bars are in the overlay, the operator DOES NOT run that part and takes it back to design.
Check out a simulator here: https://www.ncsimul.com/