Yield: 3 dozen filled cookies
Total Time: 2 hours, including dough chilling time
Special Equipment: Stand mixer, 1½-inch round cookie or biscuit cutter
3 cups (12¾ ounces) unbleached all-purpose flour
½ cup (1½ ounces) unsweetened cocoa powder
1 tablespoon baked soda
1½ teaspoons baking powder
1 teaspoon kosher salt
2 ounces semisweet chocolate, coarsely chopped (a scant 1⁄3 cup)
8 tablespoons (4 ounces) chilled unsalted butter, cut into ½-inch cubes
½ cup (3 ¼ ounces) vegetable shortening
1 cup (7 ounces) granulated sugar
2 large eggs
2½ cups (10 ounces) powdered sugar
2 tablespoons light corn syrup
2 tablespoons whole or reduced-fat milk
1 tablespoon vegetable shortening
(Want a Double Stuf Oreo? Just make twice the amount of filling and load up!)
Make the Cookies:
Whisk the flour, cocoa powder, baked soda, baking powder, and salt together into a large bowl until no lumps remain.
Melt the chocolate in a small saucepan over low heat, stirring constantly, or microwave at 15-second intervals, stirring between each burst, until liquefied. Set aside to cool slightly.
In the bowl of a stand mixer fitted with the paddle attachment, beat the butter, shortening, and sugar on medium speed for 3 to 4 minutes, until light, fluffy, and creamy. Reduce the speed to low and add the eggs one at a time, mixing thoroughly before adding the next. Pour in the melted chocolate and mix until just combined.
Add the dry ingredients and mix until a soft dough forms. Shape into two discs of roughly equal size and wrap each in plastic wrap. Refrigerate for at least 1 hour, until firm.
Preheat the oven to 375˚F and line two baking sheets with parchment paper or Silpat liners.
On a floured work surface, roll one of the dough discs to ¼-inch thickness and stamp out cookie rounds, using a 1½-inch cookie or biscuit cutter. Transfer the rounds to the prepared baking sheet and repeat with the remaining disc of dough.
Bake for 10 to 12 minutes, or until the cookies are slightly crispy at the edges and puffed but still pliable in the center. Cool completely on a wire rack before filling.
Fill the Cookies:
Using the stand mixer fitted with the paddle attachment, mix the powdered sugar, corn syrup, milk, and shortening on low speed until combined, about 30 seconds. Increase the mixer speed to medium and beat for 30 more seconds to whip slightly.
With the flat side of a cooled cookie facing up, spoon 1 teaspoon filling onto the center. Top with a second cookie, flat side down, spreading the filling evenly. Repeat to fill all the cookies.
Store the cookies at room temperature in an airtight container for up to a week.
More Edible Favor Recipes:
Hostess® Chocolate Cupcakes
McDonald's® Apple Pie