In a large bowl or stand mixer, cream together butter and sugars until fluffy. Add vanilla and pumpkin, mixing until barely combined. Slowly incorporate dry ingredients with mixer running on low. Continue mixing until no streaks remain. Transfer to an airtight container and chill overnight.
Preheat oven to 350°F. Prepare two large baking sheets with parchment paper or silicone baking mats. Cover a cooling rack with a large sheet of parchment paper.
Combine remaining cinnamon and sugar in a small bowl, to be used for the topping.
Using a small cookie scoop, take one scoop and place an unwrapped caramel square on top. Press a second small scoop over the caramel. Roll to form a ball with completely sealed edges. Roll ball in cinnamon-sugar mixture. Repeat with remaining dough.
Freeze prepared cookie dough balls in between baking batches so dough does not get too soft.
Space dough balls 2-inches apart on a prepared baking sheet. Bake for 15 minutes or until the edges are just golden. Cool 1-2 minutes on baking sheet. Carefully and swiftly, remove cookies from pan to parchment lined cooling rack.
Allow cookies to cool slightly before enjoying. Reheat as desired or serve room temperature. Store cookies in an airtight container.
Notes
*Caramel will re-harden after cookies cool completely. For a softer caramel center, microwave for 10-15 seconds or longer.An original recipe from Baked by Rachel
Nutritional information is provided as a courtesy and is an estimate only. Nutrition information can vary for a variety of reasons. For the most accurate data, use your preferred nutrition calculator with the actual ingredients you used to make this recipe.
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