Prepare the Pudding: In a medium-sized saucepan, combine 2 cups whole milk, 1/2 cup granulated sugar, 1/4 cup cornstarch, and a pinch of salt. Whisk together over medium heat until the mixture begins to simmer and thickens, approximately 5-7 minutes. Stir in 1 teaspoon vanilla extract and set aside to cool slightly.
Make the Whipped Cream: In a separate bowl, whip 1 cup heavy whipping cream until soft peaks form. Gently fold this whipped cream into the cooled pudding mixture until fully combined. This adds lightness to the pudding.
Layer the Dessert: In a large glass bowl or individual serving cups, start by adding a layer of the Biscoff cookie crumbs (approximately 1 cup). Follow this with a layer of banana slices (about 2 bananas), then a generous layer of the pudding mixture. Drizzle about 1/4 cup caramel sauce over the pudding. Repeat the layers until the ingredients are used up, finishing with a layer of pudding on top.
Top with More Cookies and Caramel: For the final layer, crush some additional Biscoff cookies and sprinkle on top. Drizzle the remaining caramel sauce over the cookie crumbs for an added touch of sweetness and garnish.
Chill: Cover the dessert with plastic wrap or a lid and refrigerate for at least 4 hours, or preferably overnight, to allow the flavors to meld and the pudding to set.