If you're a developer or tester, this means every single time. Because every start is the first time for that build...
Regarding the gdb signing, it's painful. Even more so is the privilege escalation--it's impossible to debug over ssh with gdb or lldb since the GUI prompt is on a different machine. Not having the prompt in the terminal where the debugger is being run is asinine. I had to switch to debugging on FreeBSD to avoid the pain of all this; it's madness.
Regarding the gdb signing, it's painful. Even more so is the privilege escalation--it's impossible to debug over ssh with gdb or lldb since the GUI prompt is on a different machine. Not having the prompt in the terminal where the debugger is being run is asinine. I had to switch to debugging on FreeBSD to avoid the pain of all this; it's madness.