Preheat oven to 350 degrees (F). Spray a 5 or 6-inch dish with non-stick spray and set aside.
In a medium bowl combine flour, baking soda, salt, and cinnamon.
In another medium bowl, beat softened butter, sugar, and vanilla together until soft and creamy. Add egg and beat well.
Add flour mixture in two additions, mixing until just combined after each.
Press half of the dough into the bottom of the skillet.
Spread the cheesecake filling over the dough, leaving about a 1/2 inch space on the sides.
Spread the rest of the cookie batter on top. Be sure to fully cover all of the cheesecake filling.
Sprinkle the cinnamon-sugar mixture over the top of the skillet cookie.
Place the skillet in the oven with a cookie sheet underneath it to catch any that might spill over.
Bake for about 30-35 minutes for a doughy center, 5-10 minutes longer if you would like your cookie to be more done in the center.
Remove the Sopapilla Cheesecake Skillet Cookie from the oven and serve immediately. Top with ice cream if desired.