01 - Whisk together the instant chocolate pudding mix and cold milk in a large mixing bowl for 2 minutes until the mixture thickens considerably.
02 - Gently fold the whipped topping into the pudding mixture using a spatula until completely incorporated and the texture becomes smooth and airy.
03 - Crush the chocolate sandwich cookies into fine crumbs resembling dirt using either a food processor or by placing them in a zip-top bag and crushing with a rolling pin.
04 - Assemble by spooning cookie crumbs into the bottom of 6 serving cups, followed by a layer of chocolate pudding mixture. Repeat the layers, ending with a generous topping of cookie crumbs to completely cover the pudding surface.
05 - Place 2 gummy worms into each cup, positioning them partially submerged in the cookie crumbs so they appear to be crawling out of the dirt.
06 - Refrigerate the assembled cups for at least 1 hour to allow flavors to meld and achieve optimal serving texture.