Try changing the item out for a different one, then switching it back, then going for use item type.
I had a similar issue with bandages once, as I was setting up a macro to intersperse heals and/or vetting with other stuff (as opposed to using the integral bandage macros).
Personally, though, I've gotten to the point where I just use a tool once, then hit a macro for last item/last target a number of times, and just let the tool run out, and click a new tool as needed. If a last item/last target macro is running and you click a new tool, it picks up the tool change and keeps going with the next dig after the click.