This is possibly me misunderstanding something, but I've got an outpost with 65 drillers and 4 shields being attacked by 79 drillers, a helmsman and an assassin.
Scrolling forward in time shows the outcome I lose the outpost and the attacker has 34 drillers left. When I add it up, I think he should only have 10 drillers left. Neither of the specialist seem to have an impact on the drillers.
Am I missing something?