Using a small food processor, crush Biscoff cookies. Dump into a bowl, and mix with the Biscoff spread. It will come together like wet sand.
Spoon 1-2 Tbls into the bottom of 10 small glasses. Gently press the crumbs into the bottom of the glass.
Prepare the mousse: In the bowl of an electric mixer combine cream cheese, Nutella, and milk. Beat until smooth. Slowly add the powdered sugar, and mix until fully incorporated. Using a spatula, fold in the cool whip. Spoon (or pipe) the mousse into the cups.
Prepare the whipped cream: In the bowl of an electric mixer, whip the heavy cream for 3-4 minutes until you get soft peaks. Add the powdered sugar and vanilla. Whip for an additional minute, or until stiff peaks.
Dollop cream on the mousse. Garnish with a Biscoff cookie, if desired.