01 - Whisk together instant chocolate pudding mix and cold milk in a large mixing bowl for 2 minutes until mixture thickens noticeably.
02 - Gently fold whipped topping into pudding mixture until fully incorporated and smooth, taking care not to overmix and deflate the mixture.
03 - Crush chocolate sandwich cookies using a food processor or by placing in a zip-top bag and rolling with a rolling pin until fine crumbs resemble dirt texture.
04 - Spoon cookie crumbs into bottom of 6 serving cups or jars. Add layer of chocolate pudding mixture. Repeat layers, finishing with generous topping of cookie crumbs to completely cover the pudding surface.
05 - Place 2 gummy worms into each cup, positioning them to partially emerge from the cookie dirt for a whimsical crawling effect.
06 - Refrigerate assembled cups for at least 1 hour to allow flavors to meld and achieve optimal texture before serving.