Preheat oven to 350°F. Pour out cake mix onto a rimmed baking sheet and spread into a thin, even layer. Bake until mixture reaches 165°F with an instant read thermometer, about 5 minutes. Let cool completely.
Combine cream cheese, butter and powdered sugar in the bowl of a stand mixer fitted with a paddle attachment. Beat on medium until smooth and fluffy, scraping down the bowl as needed, about 3 minutes. Add whipped topping and beat until combined. Beat in milk until creamy. Add cake mix and slowly mix until combined, then increase speed and beat until smooth. Mixture will be very thick. Mix in more milk, a tablespoon at a time, until the dip is thick but scoopable.
Transfer to a serving dish. Serve with fresh Naturipe strawberries, cookies, and crackers.