Preheat oven to 350° F. Line a cupcake pan with 12 cupcake liners.

In a small bowl or a glass liquid measuring cup, stir together semi-sweet chocolate chips, dark cocoa powder, and boiling water until the chocolate chips are melted. Set aside.

In a large mixing bowl, whisk together all-purpose flour, granulated sugar, baking soda, and salt.

Stir the chocolate mixture again to ensure that the chocolate chips are melted. Pour the chocolate mixture into the dry ingredients and whisk gently until just combined.

Add vegetable oil, eggs, and vanilla extract. Whisk until the batter is well combined and smooth.

Portion the cupcake batter into the 12 cupcake liners. Use a large cookie scoop or pour into the cupcake liners with a large liquid measuring cup.

Bake for 20 minutes or until the tops of the cupcakes bounce back slightly when gently touched or a toothpick comes out clean.

Remove the cupcakes from the oven and cool in the pan for a few minutes before transferring the cupcakes to a wire rack to cool completely.

In a large mixing bowl or the bowl of a stand mixer fitted with a whisk attachment, whip room temperature unsalted butter for 5 minutes on medium-high speed, scraping down the sides occasionally. The butter will become light, pale, and fluffy.

Add one half of the powdered sugar and mix on the lowest speed setting until fully combined. Add remaining powdered sugar and continue to mix on low until incorporated.

Add vanilla extract and salt and mix on low speed. Slowly drizzle in the heavy cream while the mixer is on low.

Increase the speed to medium-high and whip for 2-3 minutes. Scrape the sides of the bowl occasionally to ensure the frosting is well mixed.

Add the chocolate sandwich cookie crumbs and mix on low speed.

In a microwave safe bowl, combine semi-sweet chocolate chips and heavy cream.

Heat in the microwave for 30 seconds. Remove from microwave and stir.

Heat for an additional 15 seconds if needed and stir until the chocolate is melted and the ganache is smooth.

Fill a piping bag fitted with an Ateco 826 piping tip with the cookies and cream buttercream frosting.

Pipe a swirl of buttercream onto the cooled chocolate cupcakes.

Add the chocolate ganache to a small piping bag or squeeze bottle. The ganache should only be slightly warm. Drizzle the chocolate ganache over the buttercream swirl.

Place one Oreo cookie on top of the buttercream swirl.