Have gotten the shield break thing 3 times in a row and even 4 times in row but everytime i go back in he fully healed.
Hmm, shouldn't. I just tested it and what I get is you start the combat again, and see his health bar go down to the level of the prior combat end, on your first attack of the new encounter. So if he's around half, as soon as the first attack animation starts I see his health bar reset to half.
But you're fine with the damage. MC is a healing bot, and Ana hits for 60-70 each time, so it takes a few rounds.
Hmm, and when you get the shield breaking thing, you get the fairy going 'go get him his shield is down'? Do you get to him quickly? Might be a time limit between breaking the shield and combat.