Preheat the oven: Set your oven to 350°F (175°C) and line a baking sheet with parchment paper.

1. Prepare the cookie dough: In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy. Add the egg yolk, pumpkin puree, and vanilla extract, mixing until well combined.
2. Combine the dry ingredients: In a separate bowl, whisk together the all-purpose flour, salt, baking powder, pumpkin pie spice, and ground cinnamon. Gradually add the dry ingredients to the wet mixture, stirring until just combined.
3. Shape the cookies: Scoop out approximately ⅓ cup of dough for each cookie and roll into a ball. Place the dough balls onto the prepared baking sheet, spacing them about 2 inches apart. Flatten each dough ball slightly with the back of a spoon.
4. Prepare the cinnamon sugar mixture: In a small bowl, mix together the softened butter, granulated sugar, brown sugar, ground cinnamon, and all-purpose flour until well combined. Divide the mixture into 8 equal portions and place one portion of the cinnamon sugar mixture on top of each cookie dough ball, gently pressing it down.
5. Bake the cookies: Bake for 13–15 minutes, or until the edges are lightly golden. Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.
6. Prepare the cream cheese frosting: In a medium bowl, beat together the softened cream cheese, unsalted butter, vanilla extract, and powdered sugar until smooth and creamy.
7. Frost the cookies: Once the cookies have cooled completely, spread a generous amount of cream cheese frosting on top of each cookie. Using a piping bag or a ziplock bag with the tip cut off, pipe a swirl of frosting on each cookie to mimic the appearance of a pumpkin roll.