Prepare the Cream Layers:

1. In a medium bowl, whisk together the vanilla pudding mix and cold milk for 2 minutes. Refrigerate until thickened, about 5-10 minutes.
2. In a large bowl, beat the heavy cream, powdered sugar, and vanilla extract with an electric mixer until stiff peaks form, about 3-4 minutes.
3. Gently fold half of the whipped cream into the chilled pudding mixture until combined. Reserve the remaining whipped cream for layering and topping.

Prepare the Biscoff Elements:

1. Place about three-quarters of the Biscoff cookies in a zip-top bag and crush them using a rolling pin. Set aside the remaining cookies for garnish.
2. In a microwave-safe bowl, heat the Biscoff spread in 15-second intervals, stirring between each, until it reaches a pourable consistency (about 30-45 seconds total).

Assemble the Trifle:

1. Layer the bottom of a trifle dish or individual serving glasses with crushed Biscoff cookies.
2. Drizzle some melted Biscoff spread over the cookie layer.
3. Spoon a layer of the pudding-whipped cream mixture on top.
4. Add a layer of the reserved plain whipped cream.
5. Repeat the layers until all ingredients are used, ending with a layer of whipped cream on top.

Garnish and Chill:

1. Drizzle additional melted Biscoff spread over the top.
2. Sprinkle with reserved crushed cookies.
3. Decorate with whole Biscoff cookies around the edge if desired.
4. Optional: Pipe decorative rosettes of whipped cream around the perimeter.
5. Cover loosely with plastic wrap and refrigerate for at least 2 hours or overnight.