Preheat your oven to 350°F (180°C) and line a baking sheet with parchment paper to prevent the cookies from sticking.
In a large mixing bowl, beat the softened butter, granulated sugar, and brown sugar together with an electric mixer until light and fluffy, about 5 minutes. Add the egg yolk, pumpkin puree, and vanilla extract, and continue mixing until well combined and smooth.
½ cup unsalted butter, ½ cup granulated sugar, ¼ cup brown sugar, 1 egg yolk, ¼ cup pumpkin puree, 1 tablespoon vanilla extract
In a separate bowl, sift together the flour, pumpkin spice, baking powder, and salt. Slowly incorporate the dry mixture into the wet ingredients, stirring gently until just combined. Be careful not to overmix, as this will keep the cookies soft.
1 ⅔ cups flour, 1 tablespoon pumpkin spice, 1 teaspoon baking powder, ¼ teaspoon salt
Using a spoon or cookie scoop, measure out about 2 tablespoons of dough for each cookie and place them on the prepared baking sheet. Flatten each dough ball slightly with your hand.
Bake for 10 minutes, then remove from the oven even if they look a bit underbaked—they’ll set up as they cool. Transfer the cookies to a wire rack and allow them to cool completely.
For the frosting, beat together the softened cream cheese, butter, and caramel sauce in a medium bowl until smooth and creamy. Gradually mix the powdered sugar until you get a thick, spreadable frosting. Transfer the frosting to a piping bag for easy application.
½ cup cream cheese, 4 tablespoons butter, 4 tablespoons caramel sauce, ¾ cup powdered sugar
Once the cookies are cool, pipe a thick swirl of frosting onto each one. Sprinkle a little cinnamon powder over the top to finish them off. Serve and enjoy!