Missing "Web Inspector" Settings in simulator

It seems that this option is not available in the simulated devices. Tip: If you want to connect the console from your desktop Safari, you will need the Technology Preview. the normal one does not discover the simulator (though it finds the real device normally)

In my case (macOS 10.14.3 and iOS 12.1 simulators), the setting isn't there, but is active by default. Open the simulator and you should see it in Safari under Develop.

i needed to restart desktop safari. might help.

Worked for me download new Safari:
IOS Simulator: 13.4
(Safari Technology Preview)

https://developer.apple.com/safari/download/

Safari Technology Preview