Prepare your oven and equipment. Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper and set aside.
Mix the dry ingredients. In a medium bowl, whisk together the flour, baking soda, baking powder, pumpkin pie spice, and salt until well combined. This even distribution ensures perfect flavor in every bite.
Combine the wet ingredients. In a large bowl, whisk together the melted butter, oil, brown sugar, and granulated sugar until smooth and no lumps remain. The mixture should look like wet sand.
Add the egg and flavorings. Beat in the egg yolk and vanilla extract until fully incorporated. Then fold in the pumpkin puree until just combined – don’t overmix at this stage.
Create the cookie dough. Gradually add the dry ingredients to the wet mixture, stirring gently with a wooden spoon or spatula until just combined. The dough will be soft but should not be overly sticky.
Chill the dough briefly. Cover the bowl and refrigerate for 10 minutes – this short chill time helps the dough firm up just enough for easier handling without losing its chewy potential.
Form the cookies. Using a cookie scoop or tablespoon, drop rounded balls of dough (about 1½ tablespoons each) onto the prepared baking sheets, spacing them about 2 inches apart as they will spread.
Bake to perfection. Bake for 10-12 minutes, until the edges are set but the centers still look slightly underdone. They will continue cooking on the hot baking sheet after removal from the oven.
Cool properly. Allow the cookies to cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely. This resting period is crucial for developing the right texture.
Prepare the glaze. In a small bowl, whisk together the powdered sugar, maple syrup, 1 tablespoon of milk, maple extract if using, and a pinch of salt. Add more milk if needed, a teaspoon at a time, until you reach a thick but pourable consistency.
Glaze the cookies. Once the cookies are completely cool, drizzle or spread the maple glaze over each cookie. Allow the glaze to set for about 30 minutes before stacking or storing.