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For the cookies:
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1. Preheat oven to 350 F.
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2. In a large bowl, sift the flour, baking soda, salt, and baking powder together.
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3. In the bowl of your stand mixer using the paddle attachment, cream the Crisco shortening and the sugar until smooth and fluffy. Add eggs one at a time, beating after each addition. With your mixer on low speed, add half the flour mixture, followed by the vanilla and buttermilk, and then mix in the second half of the flour mixture. Finally, add the Bailey's. Mix until just combined, scraping down the bowl as needed.
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4. In a small bowl, combine the hot water, the instant coffee, and the cocoa powder. Add this to the cookie mixture and mix on low until the chocolate is fully incorporated.
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5. Drop the cookies by the spoonful onto a greased or parchment-lined baking sheet, leaving at least two inches of space between each in all directions. Bake for 10-12 minutes, until the cookies have puffed and are fully cooked. Do not over-bake. Remove cookies to a cooling rack and let cool completely before filling.
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For the filling and assembly:
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1. Combine the flour, the milk, and the instant coffee in a small saucepan set over low heat. Cook, stirring frequently, until the coffee granules are dissolved and the mixture thickens to a pudding-like consistency.
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2. In the bowl of a stand mixer, or using a hand mixer, combine the Crisco, 2 cups of the powdered sugar, the salt and the Bailey's and beat until fluffy. Slowly add the remaining powdered sugar, along with the milk and coffee mixture, and beat for another 3-5 minutes, or until the filling is very fluffy and slightly thickened. If the filling is too soft, refrigerate until firm.
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3. To fill the cookies, transfer the filling to a zip top freezer bag or piping bag and seal it. Cut a hole in one corner of the bag and place a large dollop of filling in the center of one upside down cookie. Top with a second cookie. Repeat until all the cookies have been filled.
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Substitution note: If you don't do alcohol or if you want to feel comfortable serving these to children, you can substitute the Bailey's coffee creamer they sell in the grocery store for the actual Bailey's Irish Cream liqueur. I don't know if the level of sweetness is the same, so you might have to taste as you add, but you should accomplish roughly the same thing without the alcohol.
