Prepare the Vanilla Pudding Base: In a large bowl, whisk cold milk and instant vanilla pudding mix for 2 minutes until thickened. Let rest 3–5 minutes to set.
Make the Whipped Cream: Beat heavy cream, powdered sugar, and vanilla until stiff peaks form. Do not overmix.
Combine Pudding and Whipped Cream: Gently fold whipped cream into pudding to create a light, mousse-like texture.
Prepare the Bananas and Cookies: Slice bananas into rounds and break Biscoff cookies into large chunks.
Layer the Dessert: In a trifle dish, layer pudding, cookies, bananas, caramel drizzle, and Biscoff spread. Repeat, finishing with pudding on top.
Add the Final Touches: Sprinkle crushed cookies, drizzle caramel, and chill for 4–6 hours or overnight before serving.
