Line a 24-cup muffin pan with cupcake liners, doubling up on the liners.

In a large bowl, whip together 2 cups of cold heavy cream, ½ cup of powdered sugar, and 1 teaspoon of vanilla extract until soft peaks form.

Gently fold 1 cup of Oreo cookie crumbs into the whipped cream mixture.

Pipe an even layer of the Oreo whipped cream mixture into each cupcake liner, filling it halfway.

Dip the remaining Oreo cookies briefly in whole milk and place one soaked Oreo cookie gently in each liner on top of the whipped cream.

Pipe another layer of the Oreo whipped cream mixture over the soaked Oreos.

Repeat the milk-dipping process with another layer of Oreo cookies and place them on top of the whipped cream layer.

Cover the muffin pan with plastic wrap and refrigerate for at least 12 hours.

In a clean bowl, whip together an additional cup of heavy cream with ¼ cup of powdered sugar until stiff peaks form.

Pipe the fresh whipped cream topping onto each chilled cupcake and decorate with crushed Oreo cookie crumbs.