Crush the Oreos. Place the cookies in a zip-top bag and use a rolling pin to crush until fine. You want a crumbly “soil” texture with a few small bits for crunch. Set aside.

Make the pudding. In a large bowl, whisk the instant chocolate pudding mix with cold milk per package directions. Let it thicken for 5 minutes in the fridge.

Whip the cream cheese layer. In a separate bowl, beat softened cream cheese, powdered sugar, and vanilla until smooth and fluffy. Fold in half of the whipped topping to create a light, creamy layer.

Prep your cups. Line up your mini cups on a tray. This makes assembly tidy and fast, especially if you’re doing a big batch.

Add the base layer. Spoon 1–2 teaspoons of Oreo crumbs into the bottom of each cup. Tap gently to level.

Layer the cream cheese mixture. Add a small dollop (about 1 tablespoon) of the cream cheese layer over the crumbs. Smooth lightly with a small spoon.

Add the pudding. Spoon in chocolate pudding (about 1–2 tablespoons) over the cream cheese layer. Keep the edges clean for a neat layered look.

Top with “dirt.” Finish with another layer of Oreo crumbs to fully cover the pudding. Don’t pack it down too tightly—fluffy crumbs look more like soil.

Decorate. Press a gummy worm into the top so it looks like it’s peeking out. For a fresh take, add a raspberry and a small mint leaf instead.

Chill before serving. Refrigerate the cups for at least 1 hour so the flavors meld and the layers set. Keep chilled until party time.

Optional final flourish. Right before serving, add a swirl of the remaining whipped topping on some cups for contrast and a bakery-style finish.