Ingredients

• 1/3 cup canola oil
• 3/4 cup packed light brown sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 1 1/2 cups whole-wheat pastry flour
• 1/3 cup unsweetened cocoa powder
• 3/4 teaspoon baking powder
• 3/4 teaspoon baking soda
• 1/4 teaspoon salt
• 3/4 cup nonfat milk
• 1/2 cup cold water
• 2 teaspoons unflavored gelatin
• 1 cup whipping cream
• 2/3 cup nonfat plain yogurt
• 1/2 cup confectioners’ sugar

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Cooking Directions

Step 1

Preheat oven to 350ºF. Position racks in the upper and lower thirds of the oven. Coat 2 large baking sheets with cooking spray.

Step 2

To prepare cookies: Beat oil, brown sugar, egg and vanilla in a large bowl with an electric mixer on medium speed until combined. Whisk flour, cocoa, baking powder, baking soda and salt in a medium bowl. Gradually add the dry ingredients to the wet ingredients, alternating with milk; beat until smooth. Let the batter stand for 15 minutes.

Step 3

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 doesn’t spread itself. (Each large baking sheet accommodates 8 cookies—they will be close together.) Bake the cookies until firm to the touch, about 8 minutes. Let cool on the baking sheet for 2 minutes, then transfer to a wire rack to cool completely. Wash, dry and coat the baking sheets with cooking spray again. Repeat with the remaining batter.

Step 4

To prepare filling: While the cookies cool, stir water and gelatin in a small heatproof cup or bowl. Let stand 1 minute. Microwave, uncovered, on High until the gelatin has completely dissolved but the liquid is not boiling, 20 to 30 seconds. (Alternatively, bring 1/2 inch water to a gentle simmer in a small skillet. Set the bowl with the gelatin mixture in the simmering water until the gelatin has dissolved completely.) Stir the mixture until smooth. Let cool for 10 minutes.

Step 5

Beat cream, yogurt, confectioners’ sugar and vanilla in a medium bowl with an electric mixer on high speed until very thick, about 1 minute. With the mixer beating constantly, add the gelatin mixture in a steady steam until well combined. Cover and refrigerate until the cream filling is thickened to the consistency of pudding, about 30 minutes. Whisk again until smooth.

Step 6

To assemble whoopie pies: Turn half the cookies bottom side up and top with a generous 2 tablespoons of the cream. Top with the remaining cookies. Chill in the refrigerator until the filling is set, about 30 minutes.