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You roll all of them. :). Hit and Die by guax and Prosaiko wivh is a skirmish hack of MiniBX also has a very cool alternative (and it is free). I tested 5lvl characters and this works. Thanks so much for asking, hole everything is clear.

So how about losing dice? When something breaks that first roll, do you lose one from the highest stack, or all of them?

just one, and roll the other one from the highest stack, until their are gone.

So like this?

Attack vs 5d8 + armor->Remainder vs 4d8+life -> keep repeating?

that's it! 

I’m now coming bact to this and am… Baffled at the math for attacks at higher levels. So, assuming you’re rolling your entire hit die chain to absorb, how do you actually deal damage past level 3? As far as i can tell, you don’t get any more dice to roll besides your weapon’s singular damage dice?

Indeed, you no longer roll dice for your weapon, but similar to traditional D&D mechanics, your character naturally becomes more resistant to damage as they level up.

Do you roll all of them? So like, when fighting a red dragon, one needs to make an attack that breaks a 10d8+6 defense initial defense?? I always thought you rolled each dice separately for soaking, ao trying to attack a red dragon would be Attack VS 1d8+6 and if it beats the defense the dragon's HD is reduced.

that's it, 10d8, than 9d8. And then it continues.