In a food processor, blend cookies and freeze-dried strawberries into fine crumbs. Set aside.
In a large bowl, whisk together pudding mix and half & half until smooth.
Fold in diced strawberries and refrigerate for 15–20 minutes to thicken.
Add about ½ cup of crumb mixture to the bottom of each serving cup and press gently.
Spoon about ½ cup of pudding mixture over the crumbs.
Add another layer of crumbs, then another layer of pudding.
Refrigerate until ready to serve.
Pipe whipped topping on top and garnish with remaining crumbs and fresh strawberry slices.
These creamy strawberry shortcake cups are best served chilled for the perfect texture.