Gently whisk the cold milk and vanilla pudding mix together until a becomes a thick consistency, about 2 minutes.

Chill the pudding in the fridge for 2 hours.

Place the Oreos in a food processor and blend until fully puréed.

Fold the ground Oreos into the chilled vanilla pudding.

Make the whipped cream in a stand mixer with the whip attachment*, whip the heavy whipping cream, powdered sugar, and vanilla together on medium speed for 3-5 minutes.

Once stiff peaks begin to form, gently fold the whipped cream and chocolate pudding mix into the Oreo mixture.

Chill the Oreo pudding in the fridge for 1-2 hours before using.

While the pudding chills, preheat the oven to 375ºF.

In a large saucepan, melt the butter and black coffee over a low heat until fully combined.

Remove the coffee and butter mixture from the stove. Add the cocoa powder and dark chocolate chips to the saucepan and stir until fully incorporated.

Add brown sugar, salt, and vanilla and stir.

Add the whole eggs and egg yolks into the batter and whisk until they have fully incorporated into the mixture.

Add flour and baking powder. Whisk together until fully combined.

Fill each cupcake mold about 70% to avoid overflow when the cupcakes rise during the bake.

Bake the cupcakes for 20-22 minutes or until they reach 210º F in the center. The center of the cupcake should not be wobbly and a toothpick inserted should come out clean.

Once the cupcakes have cooled completely, use a piping bag and small tip to fill each cupcake with pudding.

Use the remaining pudding to top each cupcake with piped Grey Stuff pudding.

Sprinkle the edible sugar pearls over each cupcake for a fun design and added texture.