In a large bowl, whisk the banana pudding mix and milk together for 2 minutes. Refrigerate for 30 minutes or until set.
Using an electric stand or handheld mixer, whip the heavy cream until stiff peaks form. Add 1/4 cup of the powdered sugar and mix together.
Gently fold the whipped cream into the banana pudding. Set to the side. Slice two of the bananas.
Grab your cups and line them up. Add 1/3 cup to the bottom of each cup, followed by 5 banana slices, and 4 vanilla wafer cookies. Top with 1/3 more cup of the pudding.
Cover and refrigerate until ready to serve, or up to 24 hours.
Right before serving, garnish the top with 1 tbsp wafer crumbs, more banana slices, and stand a wafer into the pudding. Enjoy!
