Begin by crushing the Oreos into fine crumbs. Use a food processor or place them in a zip-top bag and crush with a rolling pin until sand-like. Set aside about two tablespoons for garnish later.

In a large mixing bowl, beat the room-temperature cream cheese with powdered sugar and vanilla extract until smooth and creamy, about 2-3 minutes. In a separate bowl, whip the heavy cream until soft peaks form, which should take around 3-5 minutes. Gently fold the whipped cream into the cheesecake mixture until well combined.

Wash and dry one cup of fresh strawberries, then slice them evenly into thin pieces. Prepare a quick strawberry sauce by blending a few extra strawberries with sugar if desired.

Assemble by placing a layer of crushed Oreos at the bottom of each serving container. Follow with a layer of cream cheese filling, then add a layer of sliced strawberries. Repeat, finishing with cheesecake filling.

Top each cup with reserved Oreo crumbs, extra sliced strawberries, and a few mini Oreos. Drizzle with strawberry sauce if made.

Refrigerate the assembled cups for at least 30 minutes to allow flavors to meld and the filling to set.