In a medium bowl, whisk together the flour, baking soda, salt, pumpkin pie spice, and cinnamon. Set aside.
Measure 200g (¾ cup + 1 tablespoon) canned pumpkin puree and spread it over several layers of paper towels. Gently blot away excess moisture, replacing the paper towels as needed, until the pumpkin weighs approximately 110g. Do not squeeze the pumpkin completely dry. A small variation in the final weight is fine.
In the bowl of a stand mixer fitted with the paddle attachment, or using a hand mixer, beat the softened butter, brown sugar, and granulated sugar on medium speed for about 2 minutes, until smooth and creamy.
Add the egg yolk and vanilla extract and beat until fully incorporated.
Add the sourdough discard and blotted pumpkin and mix until combined.
Add the dry ingredients and mix on low speed just until no dry streaks remain. Do not overmix.
Cover the dough and refrigerate for at least 30 minutes, or until firm enough to scoop and shape. The dough can also be refrigerated overnight.
When ready to bake, preheat the oven to 350°F (175°C). Line baking sheets with parchment paper.
Use a #40 cookie scoop or a medium cookie scoop to portion approximately 1½ tablespoons of dough per cookie. Roll each portion between your palms to form a smooth ball and place about 2 inches apart on the prepared baking sheets.
For the most uniform cookies, place a small piece of parchment paper over each dough ball and gently press with the flat bottom of a measuring cup or glass until the cookie is approximately ⅓ inch thick. This method creates a rounder, more evenly shaped cookie. If you prefer thicker cookies, you can gently flatten the dough with your hand instead.
Bake for 9–10 minutes, checking the cookies at 8 minutes. The edges should be set while the centers remain soft but no longer appear wet. The cookies should not brown significantly.
Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely.
Make the Cream Cheese Frosting: Beat the softened cream cheese and butter together until smooth and creamy.
Add the powdered sugar, vanilla extract, and salt. Mix on low speed until the powdered sugar is incorporated, then increase the speed to medium and beat until smooth and fluffy.
Once the cookies are completely cooled, spread the frosting generously over each cookie using a knife or offset spatula. Alternatively, transfer the frosting to a piping bag with the end snipped off and pipe a simple spiral over each cookie.
Optional: Lightly sprinkle the frosted cookies with ground cinnamon before serving.
Notes
Pumpkin: Start with 200g of canned pumpkin puree and blot it down to approximately 110g. Removing the excess moisture is important for maintaining the texture of the cookies. Do not squeeze the pumpkin completely dry.Sourdough discard:For the best and most consistent results, use recently collected sourdough discard, ideally within 1–2 days. The discard should be thick and have a consistency similar to pancake batter. If your discard has separated and accumulated liquid, stir it thoroughly before measuring. Very thin or watery discard can add excess moisture and affect the texture of the cookies, and may make the cookies softer and more cakey. Shaping: Rolling the chilled dough into smooth balls before pressing creates the roundest cookies. A flat-bottomed measuring cup or glass with a small piece of parchment between the cup and dough provides the most consistent thickness. Hand-pressed cookies will be thicker and slightly less uniform, but are still delicious.Frosting: The cream cheese frosting makes enough to generously frost the entire batch of 26–28 cookies. If you prefer a thinner layer of frosting, you may have some leftover.Cinnamon topping: For a delicate cinnamon finish, use a fine-mesh shaker, spice sifter, or flour wand to lightly dust the frosting. You can also mix the cinnamon with a small amount of granulated sugar to make it easier to distribute evenly.StorageStore frosted cookies in an airtight container in the refrigerator for up to 5 days. For the best texture and flavor, allow the cookies to sit at room temperature for about 15–20 minutes before serving.For longer storage, freeze the unfrosted cookies in an airtight freezer-safe container for up to 1 months. Thaw completely in the refrigerator or at room temperature, then frost before serving.