TOPIC: Cloak of Shadowskin & TrueGrind

According to Tokendb, the Cloak of Shadowskin "resets itself at the beginning of every combat". TrueGrind has virtual "rooms" each of which tends to have multiple monsters, usually simultaneously.

My assumption is the cloak would work only once per "room", correct?

That is how other once per room items work in grind. But you are correct the the tokendb says once per combat but so does Bracelets of Zephyr which also says once per room.