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Soft and cake-y chocolate cookies sandwiched around sweet marshmallow Oreo frosting/fluff to make the perfect whoopie pie.
Preheat oven to 450ºF. Line two cookie sheets with parchment paper and set aside.
In a medium bowl, combine cocoa, flour, baking soda, baking powder and salt. Stir to mix. Set aside.
In the bowl of a stand mixer with the paddle attachment, cream together the shortening and sugar. Add egg, milk, and vanilla extract and mix well until combined. Slowly add the dry mixture to the wet mixture and mix well.
Using a small scoop (about 2 teaspons) scoop, place scoops of the batter onto the prepared cookie sheets (about 12 per sheet). Bake one cookie sheet at a time for 6–7 minutes (they may look underdone on the top, that’s okay). With a spatula, remove immediately to cool on a wire cooling rack.
Once the cookies have cooled completely, combining filling ingredients in the bowl of a stand mixer. Mix until completely combined. Add milk as necessary to get to a softer consistency.
Using a scoop, place a dollop of the filling in the center of the flat side of one cake. Place a matching piece of cake against the filling and push to spread the filling evenly between the two halves. Repeat until all of the pies have been filled.
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