1️⃣ In a large bowl, whisk together the vanilla pudding mix and cold milk until thickened (about 2 minutes). Stir in sweetened condensed milk and vanilla extract until smooth. Chill in the fridge for at least 10 minutes.

2️⃣ Meanwhile, make the whipped cream: In a separate bowl, beat the heavy whipping cream, powdered sugar, and vanilla extract until stiff peaks form.

3️⃣ Gently fold half of the whipped cream into the pudding mixture until well combined.

4️⃣ To assemble: Add a few vanilla wafer cookies to the bottom of each cup. Top with a layer of banana slices, then spoon over some pudding mixture.

5️⃣ Repeat the layers: cookies, bananas, pudding, until cups are nearly full. Finish with a big dollop of the remaining whipped cream.

6️⃣ Garnish with crushed cookies, banana slices, or a sprinkle of cinnamon (optional).

7️⃣ Chill cups for at least 1 hour before serving for best flavor and texture.