Make the Cookie “Crusts”:

1. Blot the Pumpkin (Do not skip!): Spread 1/4 cup of pumpkin puree on a paper towel-lined plate. Cover with another paper towel and press gently. Let it sit for 5 minutes to remove excess water.
2. Cream Butter & Sugar: In a large bowl with an electric mixer, beat the COLD butter cubes and 2/3 cup powdered sugar on low speed just until it forms a crumbly paste. (Do not over-beat!)
3. Add Flavor: Add the 1/4 cup blotted pumpkin and 1 tsp vanilla. Mix on low until just combined.
4. Add Dry Ingredients: In a separate bowl, whisk the flour, 1 1/2 tsp pumpkin spice, and salt. Add this to the butter mixture and mix on the lowest speed until a stiff dough forms.
5. Chill Dough (Essential!): Wrap the dough in plastic wrap, press it into a flat disk, and chill for at least 1 hour (or up to 3 days).

Bake the Shells:

1. Preheat: Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper.
2. Scoop & Indent: Roll the cold dough into 1-tablespoon-sized balls. Place them 2 inches apart. Dip the back of a rounded 1/2-teaspoon measuring spoon in flour and press a deep “well” into the center of each ball.
3. Bake: Bake for 12-14 minutes, until the edges are just set.
4. The “Double Indent” Trick: The wells will have puffed up. As soon as the cookies come out of the oven, immediately and gently use the same spoon to re-press the indents.
5. Cool: Let the cookies cool completely on the baking sheets before moving.

Make the Filling & Assemble:

1. Blot the Pumpkin: Blot the 1/2 cup of pumpkin puree for the filling, just like in Step 1.
2. Beat Cream Cheese: In a clean bowl, beat the ROOM TEMPERATURE cream cheese with an electric mixer until it is perfectly smooth and has no lumps.
3. Add Ingredients: Add the 1/2 cup blotted pumpkin, 1 cup sifted powdered sugar, 1 1/2 tsp pumpkin spice, and 1/2 tsp vanilla. Beat on low speed until it’s light, fluffy, and fully combined.
4. Fill: Transfer the filling to a piping bag (or use a small spoon) and fill the “well” of each completely cooled cookie.
5. Garnish & Chill: Garnish with a tiny dollop of frosting “whipped cream” (optional). Chill the finished cookies in the refrigerator for at least 30 minutes to let the filling set.