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Recipe Directions.
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Preheat oven to 350 degrees F. Position racks in the upper and lower thirds of the oven.
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Coat 2 large baking sheets with cooking spray.
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To prepare cookies: Beat oil, brown sugar, egg and vanilla in a large bowl with an electric mixer on medium speed until combined.
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Whisk flour, cocoa, baking powder, baking soda and salt in a medium bowl.
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Gradually add the dry ingredients to the wet ingredients, alternating with milk; beat until smooth.
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Let the batter stand for 15 minutes.
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Drop batter by the tablespoonful onto the prepared baking sheets, spreading the batter into a 2- to 3-inch circle with the back of a spoon if it doesnt spread itself.
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(Each large baking sheet accommodates 8 cookiesthey will be close together.)
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Bake the cookies until firm to the touch, about 8 minutes.
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Let cool on the baking sheet for 2 minutes, then transfer to a wire rack to cool completely.
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Wash, dry and coat the baking sheets with cooking spray again.
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Repeat with the remaining batter.
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To prepare filling: While the cookies cool, stir water and gelatin in a small heatproof cup or bowl.
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Let stand 1 minute.
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Microwave, uncovered, on High until the gelatin has completely dissolved but the liquid is not boiling, 20 to 30 seconds.
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(Alternatively, bring 1/2 inch water to a gentle simmer in a small skillet.
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Set the bowl with the gelatin mixture in the simmering water until the gelatin has dissolved completely.)
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Stir the mixture until smooth.
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Let cool for 10 minutes.
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Beat cream, yogurt, confectioners sugar and vanilla in a medium bowl with an electric mixer on high speed until very thick, about 1 minute.
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With the mixer beating constantly, add the gelatin mixture in a steady steam until well combined.
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Cover and refrigerate until the cream filling is thickened to the consistency of pudding, about 30 minutes.
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Whisk again until smooth.
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To assemble whoopie pies: Turn half the cookies bottom side up and top with a generous 2 tablespoons of the cream.
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Top with the remaining cookies.
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Chill in the refrigerator until the filling is set, about 30 minutes.
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Press a piece of plastic wrap directly on the surface of the filling and refrigerate for up to 1 day.
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Store the cookies in an airtight container at room temperature for up to 1 day.
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Refrigerate the assembled Whoopie Pies, uncovered, for up to 4 hours.
