Start by combining crushed chocolate cookies and melted butter. Press this mixture into the bottom and slightly up the sides of your baking dish. Chill in the refrigerator to help it firm up.
Beat cream cheese with vanilla until smooth. Gradually add powdered sugar and whipped topping, mixing until creamy and silky. Spread this layer evenly over the chilled cookie crust and return to the fridge.
Combine the instant pudding mix with milk and caramel flavoring. Mix until it begins to thicken, then fold in whipped topping until the mixture is thick and smooth.
Sprinkle chopped peanuts and turtle candies over the cream cheese layer. Drizzle chocolate and caramel syrup on top for extra indulgence. Spread the pudding mixture over this candy layer and chill for 2 hours to set.
Top the dessert with more whipped topping, peanuts, turtle candies, and drizzles of chocolate and caramel syrup. Slice into squares and serve chilled.