I am seeing issues and am able to reproduce the exact issue described if I make a few tweaks.
On first running the project and going to do a git diff, I can see the "continueAfterRunningActions" option change to "No". In addition to this, I see that the action on the breakpoint has been removed (po $0).
If I recreate the action that was removed, I am now able to see the behavior that Tres initially pointed out.
From a quick test, this appears to be an issue with single line closures. If I move the closure to be multi-line and just add a breakpoint inside the closure, I can create a breakpoint with a po $0 action that continues after running actions.
e.g.
let plusFive = [1,2,3].map {
		$0 + 5
}
–
Jordan
iOS @ WalmartLabs