Pour the milk into a mixing bowl and whisk in the chocolate pudding mix until well combined and smooth, about 2 minutes.
Allow the pudding to set in the refrigerator for about 5 minutes while you prepare the toppings.
Crush the chocolate cookies into coarse crumbs using a food processor or by placing them in a plastic bag and gently crushing with a rolling pin.
Spoon a layer of the crushed cookies into the bottom of each serving cup to resemble dirt.
Top each cookie layer with a generous layer of the prepared chocolate pudding, smoothing the surface with the back of a spoon.
Sprinkle additional cookie crumbs on top of the pudding to enhance the dirt effect and add some crunch.
Decorate each pudding cup with gummy worms, arranging them so they look like creepy crawlies burrowing into the dirt.
Place small cookie tombstones into the pudding, standing upright to resemble grave markers.
Optionally, sprinkle some extra crushed cookies on top for a more textured, dirt-like appearance.
Serve immediately or chill briefly to allow flavors to meld. Enjoy these spooky, fun dessert cups that look like a haunted graveyard!
