01 - Whisk together instant chocolate pudding mix and cold milk in a large mixing bowl for 2 minutes until mixture thickens considerably.
02 - Gently fold whipped topping into pudding mixture until completely incorporated and texture is smooth and uniform.
03 - Process chocolate sandwich cookies in a food processor or crush manually in a zip-top bag with rolling pin until fine crumbs resemble soil texture.
04 - Spoon cookie crumbs into bottom of 6 serving cups. Add chocolate pudding layer, then repeat layers ending with generous cookie crumb topping to completely cover pudding surface.
05 - Insert 2 gummy worms into each serving, positioning them so they partially emerge from the cookie dirt for realistic appearance.
06 - Refrigerate assembled desserts for minimum 1 hour to allow flavors to meld and achieve optimal serving texture.