Nutella Pumpkin Samoa Cookies

Instructions

1. Preheat the oven to 350° F. Line a baking sheet with parchment paper and set aside.
2. In a small bowl, whisk together the flour, cornstarch, pumpkin pie spice, salt, and baking powder.
3. In a large, separate bowl, beat the butter and powdered sugar together until creamy. Add in the pumpkin puree and vanilla extract beat until well-combined. Pour in the flour mixture and stir until just incorporated, making sure not to overmix.
4. Divide the dough into two halves and press them into two disks. Wrap the disks in plastic wrap and refrigerate until firm, about 1 hour.
5. When the dough firms up, roll each disk out on a lightly floured surface to about 1/8-inch thick. Cut out as many cookies as possible with a round cookie cutter, and then use a smaller cookie cutter (or spice cap) to remove the dough from the centers of the cookies, making a doughnut-like shape. Transfer the cut-out cookies to the prepared baking sheet. Repeat with the remaining dough until no dough remains.
6. Bake the cookies until they turn a light gold, about 12 minutes, rotating half-way through. Transfer the cookies to a wire wrack to cool completely.
7. As the cookies cool, prepare the coconut topping. Spread the coconut flakes evenly on a baking sheet lined with parchment paper. Bake until lightly browned, about 10 minutes, stirring frequently to make sure that the coconut toasts evenly. Set aside.
8. Add the caramels, milk and salt to a large, microwave-safe bowl and microwave for 30 seconds. Stir, and then continue to microwave in 15 second intervals, stirring in between, until the caramel is melted and smooth. Let the caramel cool slightly and spread a thin layer of caramel on top of each cookie.
9. Add the toasted coconut to the remaining caramel and mix well. Gently press the coconut-caramel mixture on top of all of the cookies.
10. In another microwave-safe bowl, combine the nutella, chocolate chips, and milk. Microwave in 15 second intervals, stirring in-between, until the chocolate is smooth. Make sure not to over-cook it or it will get grainy.
11. Whisk the confectioner's sugar into the nutella mixture to thicken it. Dip the bottoms of the cookies in the nutella mixture and place on wax paper to set. Drizzle the remaining nutella mixture over the tops of the cookies using a squeeze bottle or fork. Let set completely before serving or storing.