Scott, I always fill from the bottom and when it starts to come out of the top you should be fine. Always check after the first run to make sure that no air bubble was there and the lower unit oil is still at the top hole. When/if I need to top off, I use a tool that looks like a syringe so I can just finish it off using the top hole. Less mess that way. Check for discoloration of your old fluid and this will tell you how the prop seel is. You should change this in the fall before you store your boat, that way if the prop seal went bad over the summer and allowed water into the lower unit you will find it before it freezes and destroys your LU.