Place vanilla sandwich cookies and freeze-dried strawberries in a food processor and pulse until finely crushed. Alternatively, crush them in a sealed plastic bag using a rolling pin.
In a large bowl, whisk together the cheesecake pudding mix and milk until smooth. Refrigerate for 10 minutes to allow it to set.
Spoon a layer of cookie crumbs into the bottom of 12 small cups.
Add a layer of cheesecake pudding on top of the crumbs.
Add a layer of diced fresh strawberries.
Repeat layers if desired, then refrigerate until ready to serve.
Just before serving, top each cup with whipped topping. Enjoy your Strawberry Shortcake Dessert Cups chilled.