I have had a Kenmore 158.16012 for more than thirty years. If it is the same model, it does not wind the bobbin while loaded in the machine, but rather by using the bobbin winder on the top far right of the machine. It would be a good idea to purchase a manual -- you can find sources on the internet. It is a great machine, but such things as threading it correctly, etc are critical. Note: Once you get that bobbin wound, be certain to put it in the bobbin case correctly as the direction that it feeds through the case is counter-intuitive. It feeds from opposite the direction of the diagonal slash on the bobbin case