Failed to chmod user/Library/Developer/CoreSimulator/Devices NO Such File Or directory

I had this issue, where it would run it every time I deleted the app from the simulator, but when I tried to run it second time this error would show.

I solved it by resetting the iOS Simulator from the top bar menu.

Xcode 9.0:
Hardware → Erase All Content and Settings...

Pre Xcode 9.0:
Simulator → Reset Content and Settings...