Melt white chocolate in a microwave-safe bowl on HIGH for about 1-1 1/2 minutes, stirring every 30 seconds. Let cool slightly.
In a large bowl, beat cream cheese, powdered sugar, and vanilla with a hand mixer. Beat in slightly cooled white chocolate. Fold in whipped topping.
Finely crush 12 cookies (1 box) in a food processor (makes about 1 1/4 cups of crumbs).
Place half the cookie crumbs in the bottom of a small trifle dish (you can also use 4 small serving dishes). Press slightly to compact the crumbs, like you would if you were making a pie. Top with half of cream cheese mixture and spread evenly with a spoon. Add the rest of the cookie crumbs and press gently. Spread the rest of the filling evenly over the cookie layer.
Coarsely chop remaining 4 cookies. Sprinkle over the top of the trifle. Warm your caramel sauce and decorate the top of the trifle with it. (I put my caramel sauce in a squeeze bottle and squeezed a pattern over the top. You can also use a ziploc bag if you don’t have a squeeze bottle.) Grate 1/2 ounce of white chocolate using a box grater and sprinkle over caramel.
Store in refrigerator. This is best eaten same day, as the cookies will soften.