Chill your tools. Place a large mixing bowl and beaters in the freezer for 10 minutes. Cold equipment helps the cream whip faster and hold its shape.
Make the pudding base. In a large bowl, whisk the instant pudding mixes with cold milk for 2 minutes until thick.
Let it sit for another 2–3 minutes to fully set.
Sweeten and flavor. Whisk in the sweetened condensed milk and vanilla extract. If you like a balanced sweetness, add a small pinch of kosher salt.
Whip the cream. In the chilled bowl, beat the heavy cream and powdered sugar to medium-stiff peaks. Don’t overbeat; stop when it’s fluffy and holds ridges.
Fold to make it silky. Gently fold the whipped cream into the pudding mixture in two additions.
Aim for a light, airy texture without streaks.
Prep the bananas. Slice bananas into 1/4-inch rounds just before layering. If you’re worried about browning, you can very lightly toss slices with lemon juice, but use a gentle hand to avoid sourness.
Start layering. In a deep 13x9-inch dish or trifle bowl, spread a thin layer of pudding. Add a snug layer of vanilla wafers, then a single layer of banana slices.
Build it up. Add a generous layer of pudding over the bananas, smoothing to the edges.
Repeat with wafers, bananas, and pudding until the dish is filled, ending with pudding on top.
Top and garnish. Crumble a handful of wafers over the surface or arrange whole wafers in a neat pattern. For a fresh touch, add a few banana slices right before serving, not before chilling.
Chill to set. Cover tightly and refrigerate at least 4 hours, ideally 8–24 hours. This softens the cookies and blends the flavors.
Serve smart. For clean squares, use a 13x9-inch pan and a spatula.
For scoops, use a large spoon in a trifle bowl. Expect about 16–20 servings.