Yes, of course, Sean, you always risk getting the bar and chain stuck when sawing an undercut that deep into a head-leaner or heavy limb. But like B said. "When it starts getting tight.... power-up and ream!
Then open up the undercut nice and wide, then saw the face in deeper, open it up some more, keeping the power to the chain and reamin!
Keep at it. You can work a face-cut so deep into a head leaner it'll collapse over without even a backcut.
But under normal circumstances if you can work a face-cut over halfway into a head leaner... after that it only takes a scratch on the back to launch it. Using this technique I never had a head leaner barber-chair.
Though I will admit, the method is unconventional and quite limited in its everyday practicality, but dealing with head leaners isn't an everyday thing for a urban treeman anyway.
Caveats? You bet, there's a million. first and foremost you need a sharp chain, strong saw and you need to be quick on the draw. Plus, a sound tree is definitely in your favor. If you lack or have neither you'll probably get stuck.
Super great for alders. Barber-chairing bastards anyway. I'm sure you about alders.