Add 2.5 cups of crushed Oreo cookie crumbs and 0.25 cup of melted butter to a small mixing bowl. Stir until completely coated.

Place 2 teaspoons of the buttered cookie crumbs into each cup, tamping down with a spoon or the back of a small glass.

Using a stand mixer or handheld mixer, beat the softened cream cheese until smooth, about 1 minute.

Gradually add 0.5 cup of powdered sugar at a time, mixing well after each addition. Scrape sides as needed.

Add 1.5 cups cold heavy whipping cream and 1 teaspoon vanilla extract. Mix for 2-3 minutes until thickened.

Fold in the remaining crushed cookie crumbs gently.

Transfer the filling to a piping bag and pipe onto the cookie base in each cup, filling about 75%. Top each with one Oreo mini and refrigerate until ready to serve.