He can definitely hold out his hand, when it's clear that's the best option for Winter. He wishes it wasn't, but - it is. He's not going to waste time wishing, because that never solved anything. He's going to give Winter the space he needs, and once he's got everything he needs, he puts the bit into the drill and retreats back to the cabinets with a soft, fond "Thanks."

And then, after a moment of wiggling around awkwardly with his torso inside the cabinet, a warning, "Gonna turn on the drill," a few seconds before he does. He'll warn every time, in fact, as he works, unless Winter says something about it.