Pulse sandwich cookies and dehydrated strawberries in a food processor until finely crushed. (Or, place ingredients into a gallon plastic bag and use a rolling pin to finely crush.)

In a large bowl, combine the cheesecake pudding and milk, whisking until smooth; set aside in the fridge for 10 minutes to allow pudding to set.

Into 12 plastic cups (4 oz. each), place a spoonful or two of the cookie crumbs. Add a layer of pudding, top with diced strawberries. Refrigerate dessert cups until ready to serve.

Just prior to serving, top with a drizzle of whipped topping.