Prepare the pudding: Start by making your chocolate pudding according to the package directions. For mine, it meant whisking the pudding mix with 2 cups of cold milk until thickened. Set aside to chill while you prep the rest.

Mix the cream cheese layer: In a separate bowl, beat the softened cream cheese and butter together with an electric mixer until smooth and creamy. Add the powdered sugar and keep mixing until fully combined, then blend in the vanilla extract.

Combine the mixtures: Gently fold the cream cheese mixture into the pudding until everything is well blended. Add the Cool Whip and stir just until combined; don’t overmix, or you’ll lose that fluffy texture. Cover the bowl with plastic wrap and refrigerate while you crush the cookies.

Make the “dirt”: Place Oreo cookies in a zip-top bag and crush them with a rolling pin until they resemble fine crumbs. These will become the “dirt” layers in your dirt cake cups.

Create tombstone cookies: Use black writing gel to write “RIP” on Milano cookies for your spooky tombstones. Set them aside to dry.

Layer the cups: Spoon about 1 tablespoon of crushed Oreos into the bottom of each serving cup. Add a scoop of the pudding mixture and smooth it out with the back of a spoon or an ice cream scoop. Repeat with another Oreo layer and another pudding layer. Finish with a generous sprinkle of cookie crumbs on top (about 2 tablespoons).

Chill: Place the layered cups in the fridge for at least 30 minutes to set.

Decorate before serving: Just before serving, add your cookie tombstones, gummy worms, and festive Halloween sprinkles. This keeps the cookies crisp and the candy worms from getting soggy. Enjoy!