01 - Whisk cold milk and instant vanilla pudding mix in large mixing bowl for 2 minutes. Let stand 5 minutes until thickened.
02 - Stir sweetened condensed milk into pudding mixture until thoroughly incorporated.
03 - Whip 1 cup heavy cream to soft peaks in separate bowl. Fold whipped cream and vanilla extract into pudding base until smooth and uniform.
04 - Arrange single layer of Biscoff cookies in bottom of trifle dish or 9x13-inch baking dish.
05 - Distribute half of sliced bananas evenly over cookie layer.
06 - Spread half of pudding mixture over banana slices in even layer.
07 - Layer remaining cookies, bananas, and pudding mixture, ending with pudding on top.
08 - Cover and refrigerate minimum 4 hours or overnight for flavors to meld and cookies to soften.
09 - Whip remaining 1 cup heavy cream with powdered sugar and 1/2 teaspoon vanilla extract until stiff peaks form.
10 - Spread or pipe whipped topping over chilled pudding. Garnish with crushed Biscoff cookies and additional banana slices if desired. Serve cold.