Make the crust by adding one whole sleeve of Biscoff cookies to a food processor and blending until finely ground, like sand. Measure out 2 cups of crumbs and mix with the melted butter until combined. You should have about 2 to 3 tablespoons of crumbs left — set these aside for topping.
Prepare the filling by whisking together the pudding mix, cold milk, and pumpkin puree until smooth. Let it sit for 10 minutes to thicken. Once thickened, add the pumpkin spice, cinnamon, sweetened condensed milk, and softened cream cheese, whisking until completely smooth.
In a separate bowl, beat the heavy cream with vanilla extract until stiff peaks form. Using a rubber spatula, gently fold the whipped cream into the pumpkin pudding mixture until light and fluffy. Refrigerate until ready to use.
Assemble the layers by transferring the crust mixture to the bottom of your serving dish or cups. Press it down tightly with the bottom of a measuring cup or glass to form an even layer. Add sliced bananas and halved Biscoff cookies on top of the crust. Spread half of the pumpkin pudding mixture over the cookies, then drizzle with half of the melted Biscoff spread.
Repeat with more bananas, halved cookies, the remaining pudding, and finish with the rest of the melted Biscoff spread.
Cover and refrigerate for at least 6 hours, or overnight, to allow the cookies to soften and the flavors to meld.
Just before serving, garnish with halved Biscoff cookies, banana slices, and the reserved crushed Biscoff crumbs.