Grind cookies using a food processor until crumbly and set aside.
Mix pudding and milk and let settle in the fridge at least 10 minutes.
Mix cream cheese, butter, and confectioners sugar. Add in pudding mixture and combine until smooth.
Fold in Cool Whip until everything is combined.
Layer bottom of trifle dish with a layer of cookie crumbs. Follow with pudding mixture, alternating with cookies until everything is used up. Decorate as desired, serve and enjoy!