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1
Make the cookies: Line 3 baking sheets with parchment paper (or use 2 baking sheets and bake the cookies in batches).
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2
Preheat the oven to 400 degrees F. Using a stand mixer, beat the butter and granulated sugar until light and fluffy.
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3
Beat in the egg, then the buttermilk and vanilla.
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4
Whisk the flour, cocoa powder, baking soda, baking powder and salt in a bowl.
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5
Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
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6
Drop 8 scoops of batter, about 2 tablespoons each, onto each prepared baking sheet, spacing them 3 inches apart.
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7
Bake until the edges are set but the cookies are still soft, about 8 minutes.
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8
Remove from the oven and let the cookies cool 2 minutes on the baking sheets, then transfer to racks and let cool completely.
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9
Make the filling: Beat the cream cheese and butter in a small bowl with a mixer until smooth.
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10
Slowly beat in the confectioners' sugar until smooth.
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11
Add the pumpkin, cinnamon and salt and beat until smooth.
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12
To assemble the whoopie pies, spread a heaping tablespoonful of filling on the flat side of a cookie and sandwich with another cookie.
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13
Repeat with the remaining cookies.
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14
Photograph by Con Poulos