Preheat oven to 365 degrees F.
Mix pumpkin, sugar, oil, the egg and all spices until well blended. Slowly mix in flour and remaining ingredients. The dough will be very soft and sticky. Use a cookie dough scoop to measure out 1.5 TBSP rounds onto a greased (or parchment lined) baking sheet.
To make a rounded indent in the cookies, spray a 1 tsp measuring spoon with cooking spray and press it gently into the cookie. The dough is really soft and sticky, so you'll have to re-spray the spoon after each cookie.
Once you have all the indents made, whisk the cheesecake ingredients together until smooth and transfer to a small baggie. Snip the corner and pipe out a rounded quarter sized amount onto each cookie.
Bake for 12-13 minutes at 365 degrees F.
Cool for 2 minutes on the pan, then transfer to a baking rack. Let cool completely, then drizzle with caramel.