Place the 12 caramels into the freezer. They need to be completely cold before using.
12 Werther's soft caramels
In a medium bowl, sift the flour, cinnamon, pumpkin pie spice, baking powder, baking soda, and salt. Pour the pumpkin puree on a plate. Press paper towels over the pumpkin. Do this 3-4 times to blot out all the moisture.
2 cups All-purpose flour, 2 tsp Ground cinnamon, 1 tsp Pumpkin pie spice, 1/2 tsp Baking powder, 1/2 tsp Baking soda, 1 tsp Salt, 3/4 cup Pumpkin puree
Using a mixer, beat the butter, brown sugar, and sugar on high speed for 2 minutes. It will become lighter in color.
1 cup Unsalted butter, 1 cup Brown sugar, 1/4 cup White granulated sugar
Add in the pumpkin puree, vanilla, and egg yolk. Mix on medium until combined. Add in the dry ingredients and mix on low speed until just combined. Take off the mixer and scrape the bowl using a rubber spatula.
1 tsp Pure vanilla extract, 1 Large egg yolk
In a small bowl, mix the sugar and cinnamon. Preheat the oven to 350℉. Line two cookie sheets with parchment paper.
1/2 cup White granulated sugar, 2 tsp Ground cinnamon
Use a large cookie scoop (2 oz or 2 TBSP) to scoop the cookie dough. While still in the scoop, place your thumb into the center about 1/2 way down. Place a frozen caramel in the hole and cover back up with cookie dough.
Roll the cookie dough ball into the bowl of cinnamon sugar. Place 6 cookie dough balls per cookie sheet. Take your hand to lightly press the cookie dough ball down.
Bake for 13-15 minutes. Bake until the edges are lightly golden. Immediately top the cookie with pieces of caramel. If any caramel leaks out of the cookie, use a spoon to press the cookie back into a circle.
Let the cookie sit for 15 minutes on the pan before transferring to a cooling rack.