You need to lead him to the destination, meaning you watch where he's going and go ahead of him. I think you need to eliminate a squad before reaching the surface... the purple one will successfully escape, and you'll get his army.
No, there seems to be a bug. When I played this mission the first time, everything happened exactly as described: I freed the hero, the quest was marked as completed, and I received a new quest – to lead him to the exit. Now I'm playing it a second time. When I free this Helmar (or whatever his name is), the quest isn't marked as completed, and after 3 weeks, it says "mission failed." I've tried replaying it,