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1
Preheat the oven to 350 degrees F and position the oven rack to the middle.
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2
Line two 24-cup mini-muffin tins with cupcake liners.
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3
For the cookie crust: Combine the flour, salt and baking soda in a small bowl and set aside.
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4
Beat the butter and both sugars together in the bowl of a stand mixer fitted with a paddle attachment on medium-high speed until creamy, about 4 minutes (or in a large bowl if using an electric mixer).
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5
Add the egg and vanilla and beat until incorporated, about 1 minute.
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6
Adjust the speed to low, add the flour mixture and beat until incorporated.
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7
Fold in the chocolate chips.
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8
Drop 1 heaping teaspoon of cookie dough into each liner and press down firmly.
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9
Bake until slightly puffed and golden, 12 to 15 minutes.
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10
Cool until warm to the touch, and then press down the crust once more.
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11
Cool completely.
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12
For the brown sugar cake: Whisk the flour, baking powder and salt together in a medium bowl.
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13
In the bowl of a stand mixer fitted with the paddle attachment, beat the eggs and light brown sugar together on medium-high speed until light and foamy, about 2 minutes (or in a large bowl if using a hand-held electric mixer).
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14
While beating, gradually pour in the butter and then the vanilla.
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15
While mixing slowly, add half the dry ingredients, then add all the milk, and follow with the rest of the dry ingredients.
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16
Take care not to overmix the batter.
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17
Drop 1 heaping teaspoon of batter on top of each cookie crust.
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18
Bake until a tester inserted in the center of the cakes comes out clean, rotating the tins about halfway through, 10 to 12 minutes.
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19
Cool the cupcakes on a rack in the tins for 10 minutes, and then remove from the tins and cool on the rack completely.
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20
For the brown sugar cake: Combine the cocoa powder and butter in the bowl of a stand mixer fitted with the paddle attachment (or in a large bowl if using a hand-held electric mixer).
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21
Mix on low until combined.
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22
Add the vanilla and salt.
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23
Continue to mix on low speed and add the confectioners' sugar and milk in alternating batches.
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24
Increase the speed to medium-high and mix until fully incorporated and smooth.
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25
Fill a pastry bag fitted with a round or star tip and pipe small chocolate drops on top of each cupcake.