We have always been told by all airlines here in North America, and we have flown with many, that your first port of entry you must claim luggage and then recheck them in. It has always held true for our flights. Before we started to fly Air Canada we would have to have a stopover in the US and we always had to claim our luggage and recheck them. Our first time to Jamaica we had to do this 5 times going there and 5 times coming home. What a nightmare!! We said we didn't care how much tickets were for a more direct flight we would be willing to pay it if we went to JA again. With Air Canada we go from Edmonton to TO then on to Sangster, same on return. Hope this helps you out.