Guys, let me discuss this.
First, the extendable tongue is galvanized steel. What is occuring is the entended tongue is bent which is why it is not going into the receiver most of the time. This happened to me as a dealer who was involved with this boat heavily. There was a rare occasion that the channel the extended tongue was not welded on correctly originally at the time of manufacturer or the reciever was not put on correctly. First is to determine what is going on first.
The suggestion to loosen the winch strap is the first to do. Then investigate from there. However, many extendable tongues do not have those recievers and some chose to elimiante them altogether. Doing so, it would rattle a little in the channel tube. You may have to reweld that reciever and there is spray can paints that can protect the steel if applied on after welding. Before doing that, I would insure the bar can slide thru all the way thru that channel tube and if not, then you have a bent extended tongue.
Big Chief, feel free to contact me and if you do not know me, then ask here.