For the baker with a laid-back personality, these Baileys espresso cream cupcakes are perfect. The ingredients for these cupcakes reflect an easygoing attitude — espresso for a smooth persona, Baileys for an inviting smile, and a sugar cookie base for a sweet demeanor.
Cream together the butter, sugar, and salt in the bowl of an electric stand mixer on medium-high speed until light and fluffy, about 3 minutes. Add the egg yolk and beat well before adding whole egg.
Add the vanilla extract and beat until well incorporated. Next, add the flour and beat at low speed just until the flour is mixed in. Do not overmix. Divide the dough in ½ and wrap in plastic. Refrigerate until firm, at least 1 hour and up to 2 days.
Preheat the oven to 375 degrees.
Soften ½ of the dough at room temperature for 15 minutes. Reserve the other ½ for another use. Lightly flour a work surface and quickly roll out the dough until it is ¼-inch-thick, flouring the top side of the dough as well to prevent it from sticking to rolling pin.
Line a cookie sheet with parchment paper. Stamp out small cookies using a cookie cutter of your choice and place on the cookie sheet. Place in the oven and bake until the edges are slightly golden, about 8-10 minutes. Remove from the oven and let cool on a rack.
Put the chocolate in a small, heatproof bowl. Bring the cream to a simmer in a small pan over medium-low heat. Remove from heat, then quickly stir in the espresso powder and Baileys. Pour over the chocolate and let sit for 1 minute. Stir until combined and set aside.
Preheat the oven to 350 degrees.
Place cupcake liners in a muffin pan. In a medium-sized bowl, sift together the flour, baking powder, baking soda, and salt. Whisk in the granulated sugar. In another bowl, whisk together the oil, milk, and 2 teaspoons of the vanilla extract. Pour the wet ingredients into the dry ingredients and whisk to combine.
Mix only until relatively smooth and fill the cupcake liners with a scant ¼ cup batter. The cupcake liner should be just under 2/3 of the way full. Transfer to the oven and bake until golden and a toothpick inserted in the center comes out clean, about 20-22 minutes. Remove from the oven, transfer to cooling rack, and allow to cool to room temperature.
Meanwhile, put a medium-sized mixing bowl and the whisk attachments from the electric mixer in the freezer for 20 minutes. Remove from the freezer and combine the heavy cream, sour cream, sugar, remaining vanilla extract, and pudding in the bowl. Use an electric mixer on high speed to whip to stiff (but not grainy) peaks, about 1-2 minutes. Set the vanilla cream aside.
Pour the warm chocolate sauce into resealable plastic sandwich bag. Snip off the corner to make a very small hole. Drizzle the sauce decoratively onto the cooled cookies and cupcakes. Fit a piping bag with a large star tip, set in a water glass and fill halfway with vanilla cream. Pipe a towering swirl on each cupcake, top with a cookie, and serve.