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1
For the cookies: Whisk together the flour, cocoa, baking soda, baking powder and salt in a large bowl.
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2
Sift into another large bowl.
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3
Beat the granulated sugar and butter together in a large bowl with an electric mixer on medium-high speed until light and fluffy, about 5 minutes.
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4
Add the egg and beat until incorporated.
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5
Beat in the vanilla.
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6
Alternate adding the dry mixture and the milk, beginning and ending with the dry mixture.
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7
Mix until just incorporated.
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8
Refrigerate the dough until chilled, about 1 hour.
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9
Adjust the oven racks to the top and bottom thirds of the oven and preheat to 400 degrees F. Line 2 baking sheets with parchment and lightly coat with cooking spray.
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10
Drop tablespoonfuls of batter about 3 inches apart on the prepared baking sheets (about 6 cookies per baking sheet).
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11
Keep the remaining batter chilled while working.
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12
Bake until the cookies puff up and the tops are no longer glossy, about 7 minutes.
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13
Let cool for a few minutes on the baking sheets, then transfer to a wire rack to cool completely, about 1 hour.
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14
Let the baking sheets cool, then reline with parchment, lightly coat with cooking spray and bake the remaining batter in batches (cool, reline and spray the baking sheets each time).
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15
For the filling: Beat the confectioners' sugar and shortening in a large bowl with an electric mixer on medium speed until fluffy.
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16
Add the marshmallow creme, milk and peppermint extract and beat until light and airy, about 5 minutes.
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17
Spread a heaping tablespoon of the filling on half of the cookies.
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18
Sandwich with the remaining halves, pushing down slightly to move the filling to the edge.
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19
Put the crushed candy canes on a plate and roll the sides of the whoopie pies in the candy.
