Brew 1/2 cup of coffee and set aside to cool. You can brew the coffee however you prefer your coffee or follow the instruction on the coffee bag. I used 1 rounded tablespoon of ground coffee and about 5 oz of water.
Preheat oven to 350°F and line a regular size cupcake pan with cupcake liner.
Add buttermilk, egg, oil and vanilla extract in a bowl or measuring cup and beat to combine.
Sift all the dry ingredients, flour, cocoa powder, sugar, salt, baking soda, and baking powder together in the bowl of your standmixer. Fit the mixer with the paddle attachment and mix to combine.
With the mixer on low speed, pour the wet ingredients into the dry mixture. Mix until combined. Then slowly pour the coffee in with the mixer still on low speed. Mix again only until combined.
Stop the mixer and use a spatula to scrape the side and bottom of the bowl and make sure everything is thoroughly mixed.
Use an ice cream scoop to divide batter equally among 12 cups, it will be about 2/3 to 3/4 full. Bake at 350°F for 17 minutes. Inserted toothpick in the middle of the cupcake should come out clean. Cool the cupcakes on a wire rack.
To prepare the frosting, chill a mixing bowl and the whisk attachment in the freezer for 10 minutes.
Meanwhile, ground up 4 to 5 Oreo cookies in a food processor or blender to make 1/2 cup of ground Oreo. Process until everything is coarse and mealy. You don’t want too fine crumbs, but not too large either.
Whip 1 cup of heavy whipping cream with 1/4 cup of sugar and 1/4 teaspoon of vanilla extract on medium high speed until stiff peak forms. Transfer to another bowl and place in the fridge.
Place the soften cream cheese in the same mixing bowl you just made the whipped cream, 1/4 cup of sugar and 1/4 teaspoon of vanilla extract. Beat until everything is incorporated and creamy.
Fold the whipped cream into the cream cheese mixture with a spatula. Then fold the ground Oreo into the cream. Place into the freezer for 15 – 30 minutes to set.
When the cupcakes cool completely, you can assemble them.
Fill a pastry bag fitted with a large star tip with the cookies and cream frosting. To fill the cupcakes, just stab the tip down in the middle of the cake and give the frosting bag a slight squeeze, continue until you see the cupcake expands a little bit. You may only need to squeeze once to get enough filling in there.
Use the same pastry bag and star tip to top the cupcake with frosting.
Garnish each cupcake with half an Oreo cookie.
Refrigerate until ready to serve.