In the auto-continue after we stop at the start point when running the debugger asynchronously, we use PrivateResume to continue. But that doesn't update the stop locker state, which is currently at "stopped". That means the stop locker wasn't doing its job to prevent you from running expressions while the target is running.
I fixed this, and added a test for this case to make sure we get a proper error back. This patch requires (and adds the test for):
@jingham, you're testing the same thing twice. You probably wanted to set the stop_at_entry argument to True here.