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1
Make the cookies: Preheat oven to 350 degrees (F). Line two baking sheets with parchment paper or a nonstick baking mat; set aside. (Or spray lightly with a non-stick spray)
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2
In a medium bowl, whisk together flour, salt, baking powder, baking soda, cinnamon, ginger, and cloves; set aside. In a large bowl, whisk together brown sugar and oil until well combined. Add pumpkin puree and whisk until combined. Add eggs and 1 teaspoon of vanilla and whisk until well combined. Sprinkle flour mixture over pumpkin mixture and stir until fully incorporated.
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3
Using a small ice cream scoop with a release mechanism, drop heaping tablespoons of batter onto prepared baking sheets, about 1 inch apart (you can also use a Tablespoon measuring spoon rather than the scoop). Transfer to oven and bake until a toothpick inserted into the center of each cookie comes out clean, about 15 minutes. Let cool completely on pan.
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4
Make the filling: Sift confectioner's sugar into a medium bowl; set aside. In the bowl of an electric mixer fitted with the paddle attachment (or just use a hand mixer with regular beaters), beat butter until smooth. Add cream cheese and beat until well combined. Slowly add powdered sugar and remaining vanilla, beat just until smooth. Filling can be made up to a day in advance. Cover and refrigerate; let stand at room temperature to soften before using.
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5
Assemble the whoopie pies: Match cookies up for similar sizing. When cookies have cooled completely, pipe or spread a large dollop of filling on the flat side of half of the cookies. Sandwich with matching cookies, pressing down slightly so that the filling spreads to the edge of the cookies. Refrigerate cookies at least 30 minutes before serving and up to 5 days.
