Place the vanilla sandwich cookies and freeze-dried strawberries into a food processor.
Pulse until the mixture becomes fine crumbs.
Alternatively, place the ingredients in a large resealable plastic bag and crush them with a rolling pin.
In a large mixing bowl, whisk together the cheesecake pudding mix and milk until smooth.
Refrigerate the pudding mixture for about 10 minutes until thickened.
Prepare 12 clear plastic dessert cups (4-ounce size).
Add 1–2 spoonfuls of the strawberry cookie crumb mixture to the bottom of each cup.
Spoon a layer of pudding over the crumbs.
Add a layer of diced fresh strawberries.
Repeat layers if desired.
Refrigerate the Strawberry Shortcake Dessert Cups until ready to serve.
Just before serving, top each cup with whipped topping.