Mix the pudding base. In a bowl, whisk cold milk and instant vanilla pudding for about 2 minutes until thickened. Let it sit for 5 minutes to set.
Whip the cream. In a separate bowl, whip heavy cream with powdered sugar, vanilla, and a pinch of salt until soft peaks form.
Don’t overwhip.
Fold and chill. Gently fold the whipped cream into the pudding until smooth and fluffy. Cover and chill while you prep the layers.
Salt the caramel. Stir flaky sea salt into the caramel sauce. Start with 1/4 teaspoon and taste.
You want a pleasant salty edge, not a salt bomb.
Layer the cookies. In a 9x9-inch dish or similar, add a single layer of vanilla wafers. It’s fine if there are small gaps.
Add bananas. Arrange a layer of sliced bananas over the cookies. Keep slices about 1/4-inch thick so they hold up well.
Spread the pudding. Spoon about half the pudding mixture over the bananas and smooth it gently to the edges.
Drizzle caramel. Add a thin, even drizzle of salted caramel over the pudding.
Don’t drown it—just enough to taste in every bite.
Repeat. Add another layer of cookies, bananas, the rest of the pudding, and another light drizzle of caramel.
Top and chill. Finish with a few crushed cookies and a final, delicate swirl of caramel. Cover and refrigerate for at least 4 hours (overnight is best) to let the cookies soften and flavors meld.
Serve. Garnish with fresh banana slices and a pinch of flaky salt just before serving. Scoop or slice and enjoy.