Step-by-Step Instructions

1. Prepare the Cookie Crumbs: Place chocolate sandwich cookies into a food processor and pulse until they become coarse crumbs, about 30 seconds.
2. Transfer crushed cookies into a medium mixing bowl, keeping aside 1 cup of crumbs for topping.
3. Make the Chocolate Pudding: Pour cold whole milk into a large bowl, add instant pudding mix and whisk for about 2 minutes until thick.
4. Refrigerate the pudding for 5 minutes.
5. Create the Cream Cheese Mixture: In another bowl, beat together softened cream cheese, 1/4 cup powdered sugar, and 1 tsp vanilla extract until smooth.
6. Combine the Pudding and Cream Cheese: Add chocolate pudding to cream cheese mixture and beat on low speed until fully combined.
7. Fold in the Whipped Topping: Gently fold the thawed whipped topping into the chocolate mixture until light and airy.
8. Assemble the Cup Layers: Divide cookie crumbs among cups, pressing lightly. Spoon pudding filling over crumbs.
9. Add the ‘Dirt’ Topping: Sprinkle reserved cookie crumbs over pudding layers.
10. Chill the Cups: Cover and refrigerate for about 30 minutes.
11. Prepare the Buttercream Frosting: Beat softened butter until pale and fluffy, then gradually add powdered sugar while mixing.
12. Mix in Cream and Flavor: Add heavy whipping cream and remaining vanilla extract. Beat until frosting is thick and fluffy.
13. Color the Frosting: Add green gel food coloring and mix until achieving desired shade.
14. Pipe the Frosting Trees: Use a piping bag to create tree shapes on top of each cup.
15. Add Decorations: Sprinkle red and white sprinkles and place a yellow star on top.
16. Final Chill Before Serving: Refrigerate for an additional 15 minutes before serving.