In a mixing bowl, combine 1 ½ cups of finely crushed chocolate sandwich cookies with 5 tablespoons of melted unsalted butter. Stir until the mixture resembles wet sand.

Take 28 2-ounce plastic cups and evenly distribute the cookie crumb mixture into each cup. Press down firmly to form a compact layer.

In a large bowl, beat 8 ounces of room-temperature cream cheese with ½ cup of granulated sugar until smooth, about 2-3 minutes. Add 1 teaspoon of pure vanilla extract and briefly beat to combine.

In a separate bowl, pour 1 cup of heavy cream and whip it until soft peaks form, approximately 3-4 minutes.

Gently fold in ½ cup of additional crushed chocolate sandwich cookies into the cream cheese mixture.

Using a piping bag or a spoon, fill each prepared cup with the creamy mixture, stopping about three-quarters full.

Top each filled cup with a mini chocolate sandwich cookie or a sprinkle of crushed crumbs. Cover and refrigerate for 2-3 hours.