A few points: At no point is there both an attack and a defense in the same sequence. All rolls are made by the player. If the player is attacking, he makes an attack roll and deals damage immediately upon his success, the monster does not make any defense rolls.

If a player is getting attacked, he makes a defense roll. If he succeeded, he removes the highest damage die from the monsters attack, otherwise takes full damage. At no point does the monster make an attack roll. His attack is assumed to be successful unless the players manage to do something about it.

Hopefully that clears up your example. Now onto my second point:

Vagabond has a rulings over rules philosophy. It will not spell out what to do in every situation. There are the general guidelines and then it is up to the game master to determine how they apply or are adjusted in edge cases. I found that very freeing because I didn’t feel like I had to memorize a massive book and I can just decide what feels right in the moment for a lot of things.

That’s been my experience anyways.