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1
Sift together flour, cocoa powder, baking soda, baking powder, espresso powder, and salt in a medium bowl and set aside.
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2
In a large bowl, beat the butter and sugar together in a large bowl until combined. Add the egg and vanilla and beat until smooth. Add flour mixture and stir with a wooden spoon until all the flour is incorporated.
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3
Wrap the dough in plastic and gently press it into a disk. Refrigerate for at least an hour (and up to several days).
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4
When you are ready to bake the cookies, preheat the oven to 350u00b0 F and line a baking sheet with parchment. On a lightly floured surface, roll out the dough, dusting with more flour if needed, to about 1/4 to 1/8 inch thick. Use a round 1 1/2-inch cookie cutter to stamp out as many cookies as possible and reroll the scraps as necessary. Bake for 7 to 9 minutes or until the tops have set and no longer look wet. Transfer to a wire rack and let cool completely.
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5
Meanwhile make the filling: In a large bowl beat together butter and shortening until combined. Add 2 cups powdered sugar and beat for several minutes until smooth. Add the vanilla extract and seeds and mix until incorporated.
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6
Transfer about half the filling to a small bowl -- this is your booze-free filling. Add the bourbon and 1/3 cup powdered sugar to the remaining filling and beat until combined - this is your booze filling.
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7
Use an offset spatula to spread a small amount of frosting on the bottom side of half of the cookies. Place the remaining cookies on top and gently squeeze each sandwich together to spread the filling to the edges. Filled cookies can be stored in an airtight container in the fridge for several days.
