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 texture becomes smooth and creamy.
03 - Crush chocolate sandwich cookies in a food processor or place in zip-top bag and roll with rolling pin until fine crumbs resemble dirt texture.
04 - Spoon cookie crumbs into bottom of 6 serving cups or jars. Add chocolate pudding mixture on top. Repeat layers, finishing with generous cookie crumb topping to completely cover pudding surface.
05 - Decorate each cup with 2 gummy worms, positioning them to partially emerge from crumbs for realistic crawling effect.
06 - Refrigerate assembled dirt cups for minimum 1 hour before serving to allow flavors to meld and achieve optimal texture.