01 - In a large mixing bowl, whisk together the instant chocolate pudding mix and cold milk for 2 minutes until mixture thickens considerably.
02 - Gently fold the whipped topping into the pudding mixture until fully incorporated and smooth, taking care not to deflate the mixture.
03 - Crush the chocolate sandwich cookies using a food processor until fine crumbs form, or place them in a zip-top bag and roll with a rolling pin until they resemble soil texture.
04 - Spoon a layer of cookie crumbs into the bottom of 6 serving cups or jars. Add a layer of chocolate pudding mixture. Repeat layers, finishing with a generous topping of cookie crumbs to completely cover the pudding surface.
05 - Decorate each cup with 2 gummy worms, positioning them so they appear to crawl out of the dirt by partially embedding them in the cookie crumb layer.
06 - Refrigerate the assembled dirt pudding cups for at least 1 hour to allow flavors to meld and achieve optimal texture before serving.