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In a large bowl, whisk the pudding mix and cold milk for 2 minutes until thickened.
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Let the pudding sit for 5 minutes to fully set.
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In a separate bowl, whip the heavy cream, powdered sugar, and vanilla extract until stiff peaks form.
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Gently fold the whipped cream into the pudding until smooth and fluffy.
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Spread a thin layer of pudding mixture in the bottom of a trifle dish or 9×13-inch dish.
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Add a layer of Biscoff cookies, breaking them as needed to fit.
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Add a layer of banana slices, then drizzle caramel sauce and Biscoff cookie butter over the bananas.
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Repeat the layers until all ingredients are used, finishing with a layer of pudding on top.
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Cover and refrigerate for at least 4 hours, preferably overnight.
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Before serving, top with crushed Biscoff cookies and an extra drizzle of caramel.