Cookies and Cream Cupcakes

Preheat the oven to 350℉ (177℃). Line a cupcake pan with 12 cupcake liners.
In a small bowl, stir together the semisweet chocolate chips, dark cocoa powder, and boiling water until the chocolate chips are melted. Set aside to cool.
In a large mixing bowl, whisk together the all-purpose flour, granulated sugar, baking soda, and salt. Add the cooled chocolate mixture and whisk until well combined. Add in the vegetable oil, eggs, and vanilla extract and whisk until the cupcake batter is smooth.
Portion the cupcake batter into the cupcake liners using a large cookie scoop (about ⅔ full). Bake the cupcakes for 20 minutes and then transfer to a wire rack to cool completely.

In the bowl of a stand mixer fitted with a paddle attachment or in a large mixing bowl with an electric hand mixer, cream the unsalted butter for 5 minutes until light, pale, and creamy.
Add one half of the powdered sugar and mix on the lowest speed setting until fully combined. Add the remaining powdered sugar and continue to mix on low speed until incorporated. Add the vanilla extract and salt and mix on low speed until combined. Drizzle in the heavy cream. Scrape the sides and bottom of the bowl to be sure the ingredients are well combined.
Turn the mixer to medium speed and whip the buttercream for about 2 to 3 minutes until it is smooth and creamy.
Add in the Oreo cookie crumbs and mix the frosting on low speed until the cookie crumbs are dispersed throughout the frosting. Scrape the sides and bottom of the bowl as needed. Mix the buttercream for several minutes on low speed to remove air bubbles.

Combine the semisweet chocolate chips and heavy cream in a microwave-safe bowl. Heat in the microwave for 30 to 45 seconds. Allow the mixture to sit for 1 minute. Stir well until the chocolate is melted and the ganache is smooth. Cool slightly before drizzling onto the cupcakes.

Fill a piping bag fitted with an Ateco 826 piping tip with the cookies and cream buttercream frosting. Pipe a generous swirl of buttercream onto the cooled chocolate cupcakes. Drizzle the slightly cooled chocolate ganache onto the cupcakes and decorate with halved Oreo cookies.

Store the cupcakes in an airtight container at room temperature for 1 to 2 days or in the refrigerator for 2 to 3 days. Serve at room temperature.

Metric conversions are calculated automatically. I cannot guarantee the accuracy of this information.