In a mixing bowl, combine the 3.4 ounces of instant chocolate pudding mix with 2 cups of milk. Whisk vigorously for about two minutes until the mixture is smooth and thickened.
Once the pudding has set, gently fold in the 8 ounces of thawed whipped topping with a spatula. Be careful not to deflate the whipped topping; you want to maintain that light and airy texture.
Place the 10-12 Oreo cookies in a plastic bag and crush them into small pieces using a rolling pin or your hands. The pieces should be a mix of fine crumbs and slightly larger chunks for texture.
Start layering your Dirt Cups. Begin with a layer of the pudding mixture at the bottom of your serving cups, followed by a layer of crushed Oreos. Repeat this process until the cups are filled, finishing with a generous layer of crushed Oreos on top.
Finally, place the 32 gummy worms on top of the Oreos, letting them hang over the sides for that playful “dirt” effect.
Refrigerate the Dirt Cups for at least 30 minutes before serving. This allows the flavors to meld and gives the pudding time to firm up a bit. When ready to serve, grab a spoon and dig in!