Preheat the oven to 350°F (175°C). Lightly oil a mini muffin tin or spray with nonstick spray.
Prepare the 16 ounces sugar cookie dough per the package directions or your recipe, or remove premade dough from its package.
Scoop and roll the cookie dough into 1-tablespoon balls. Place one dough ball into each cup of the mini muffin tin.
Bake for 10–15 minutes, until the cookies are lightly browned and cooked through. Baking time will vary by dough—watch them closely.
Immediately after removing the tin from the oven, press the back of a 1/2-teaspoon measuring spoon (or similar small rounded tool) into the center of each warm cookie to form a cup. Press gently to avoid cracking.
Let the tin cool for several minutes until safe to handle. Remove the cookie cups from the tin and finish cooling on a wire rack until completely cool.
While the cookie cups cool, place the 8 ounces cream cheese in a large mixing bowl and whip with an electric mixer until light and fluffy.
Add 1/2 teaspoon vanilla extract and 1/8 teaspoon salt to the cream cheese and mix until combined.
Add the 2 cups powdered sugar, 1 cup at a time, mixing fully after each addition until the filling is smooth and spreadable.
If the fruit is not already diced, dice a total of 1 cup of fruit (strawberries, blueberries, raspberries, kiwi, mandarin oranges) into small pieces.
Fill each cooled cookie cup with the cream cheese mixture using a piping bag, a zip-top bag with the corner cut off, or a spoon.
Top each filled cookie cup with the diced fruit. Serve immediately.