Cream Cheese Filling: To a small bowl, beat together the cream cheese, powdered sugar, vanilla extract, and cinnamon for 1–2 minutes until smooth and creamy. Transfer the mixture to a piping bag and pipe 18 mounds onto a parchment-lined baking sheet. Place the fillings in the freezer to chill while you prepare the cookie dough.

Preheat the oven to 400ºF convection.

Mix wet ingredients: To a medium-sized bowl, beat the softened butter until light and fluffy. Add the brown sugar and granulated sugar, and cream together until smooth. Mix in the sourdough discard, canned pumpkin, and vanilla extract. Beat until fully combined.

Mix dough together: To a small bowl, add the flour, baking powder, baking soda, salt, cinnamon, and pumpkin pie spice. Whisk together to combine. Add the flour mixture to the butter mixture and mix until the wet and dry ingredients are fully incorporated.

Stuff Cookies: Using a cookie scoop, portion the dough into 18 pieces. Remove the cream cheese fillings from the freezer and press one into the center of each portion. Shape the dough around the filling, sealing it completely.

Coat and Bake: In a small bowl, mix together the granulated sugar and pumpkin pie spice. Roll each dough ball in the mixture until fully coated. Place 9 dough balls on a parchment-lined baking sheet and press down lightly with your hand. Bake at 400ºF for 10 minutes. Allow the cookies to cool on the baking sheet until mostly set before transferring to a wire rack.