There is an actual issue that I've seen. Start with one equipped, have mafia set to re-equip things that break. Start a bunch of automated turns. When the item breaks, it is replaced, over and over. When adventuring stops due to reaching the specified number of turns, it is unequipped. It seems like a checkpoint is being created before the item is re-equipped, and then it is restored at the end of adventuring.
I haven't actually looked at the code for any of that, and it's been a while since I used a sugar shield for farming so I don't think about it much.