Prepare pudding:
In a large mixing bowl, whisk pudding mix with cold milk until thickened, about 2 minutes.
Add creaminess:
Stir in sweetened condensed milk until smooth. Gently fold in whipped topping until fully combined.
Layer the cups:
In small glass cups or jars, start with a layer of crushed vanilla wafers, followed by pudding mixture, banana slices, and a drizzle of caramel sauce.
Repeat layers:
Continue layering until the cups are filled, finishing with pudding on top.
Garnish:
Top with whipped topping, banana slices, more caramel drizzle, and a sprinkle of crushed cookies.
Chill:
Refrigerate for at least 1 hour before serving to let the flavors meld and the texture set.
Variations:
Use graham crackers, Biscoff cookies, or shortbread in place of vanilla wafers.
Swap the caramel for dulce de leche for an ultra-rich twist.
Add a layer of chocolate shavings or chopped toffee for crunch.
Tips:
Toast crushed wafers lightly in the oven for a deeper, nutty flavor.
To prevent bananas from browning, toss slices in a little lemon juice before layering.
Assemble just before serving if you prefer your cookie layers extra crisp.