Seal the Oreo cookies in a plastic bag and crush them with a rolling pin or sturdy wooden spoon, then spoon 1 1/2 - 2 tablespoons into each of 6 small dessert dishes that hold at least 3/4 cup-1 cup. The crumbs should be a mix of fine bits and coarse pieces so the base stays textured instead of turning uniformly soft.

Beat the softened cream cheese with the powdered sugar using a hand mixer or stand mixer until the mixture is fully smooth, then mix in the vanilla. When it is ready, it should look creamy and even, with no small white lumps clinging to the bowl or beaters.

Fold in the Cool Whip gently, then fold in the remaining crushed Oreos once the filling is light and combined. The mixture should smell sweet and creamy, and it should hold soft swoops instead of looking thin or deflated.

Divide the filling evenly among the prepared dishes and lightly press it over the cookie layer, then chill for about 1 hour or until ready to serve. The cups are set when the surface feels cool and softly firm to the touch rather than loose or wobbly.

Finish each cup with whipped cream and extra crushed Oreos right before serving. The topping should sit neatly on the chilled filling without sinking, which tells you the cups are properly set.