I've just acquired the Square, purchased an iPad, and downloaded apps for both the Square Card Reader and Square Register. I've added 13 items to the Item Library in Register, with lots more to come. According to Square FAQ, all that I enter into the Register's Item Library should transfer over to the Square Card Reader. They do, mostly. Of the 13 items I currently have, all descriptions and prices transfer over, but only 6 have images attached. The other 7 have a black square with the number "13" in it. Square's help line has not yet responded, so I thought someone here might have a clue.
All images are coming from the same location - the iPad's Photo app. Why some and not the others?