Servings
Font
Back
4.6 from 234 votes

Pineapple Upside Down Sugar Cookies

Pineapple upside down sugar cookies are the perfect summer treat and after that tasty pineapple and cherry are gone, you still have a soft, fluffy sugar cookie!

Prep Time
20 mins
Cook Time
20 mins
Total Time
45 mins
Servings: 13 cookies
Calories: 519 kcal
Course: Dessert
Cuisine: American

Ingredients

  • 1 cup butter room temperature
  • 1 1/2 cups granulated sugar
  • 2 eggs
  • 2 tsp. vanilla extract
  • 1/2 cup sour cream
  • 3 cups all-purpose flour
  • 1 tsp. baking powder
  • 1 tsp. cornstarch
  • 1/2 tsp. salt
  • 13 canned pineapple slices
  • 13 Maraschino cherries
  • 1/2 cup butter melted
  • 1 cup light brown sugar packed

Instructions

    Cup of Yum
  1. Preheat oven to 350 degrees. Set aside the USA pan mini round cake pan.
  2. In a large mixing bowl, add in the butter and sugar and mix until light and fluffy.
  3. Add in the eggs, vanilla extract, and sour cream and mix until combined.
  4. Add in the flour, baking powder, cornstarch, and salt. Mix until the cookie dough just comes together. Set aside.
  5. In a separate bowl, stir together the melted butter and brown sugar until combined.
  6. Add about a tablespoon of the brown sugar mixture into the bottom of each cavity. Spread it around to cover the bottom.
  7. Add the pineapple slice on top of the brown sugar and the cherry in the center of the pineapple.
  8. Add a 3 T. cookie scoop of cookie dough to the top. Using an offset spatula, flatten it out. 
  9. Place into the oven and bake for 25 minutes or until the edges are golden brown and the brown sugar is bubbling up the sides. 
  10. Let cool for 10 minutes and then turn out onto a wax paper covered surface. Brown sugar will run all over, so the wax paper is necessary. If the pineapple sticks to the pan, just reposition it back on the cookie.
  11. Let cool completely before eating. Store in an airtight container. These are best if ate within the first 2 - 3 days. 

Nutrition Information

Calories 519kcal (26%) Carbohydrates 73g (24%) Protein 4g (8%) Fat 23g (35%) Saturated Fat 14g (70%) Cholesterol 86mg (29%) Sodium 283mg (12%) Potassium 188mg (5%) Fiber 1g (4%) Sugar 49g (98%) Vitamin A 775IU (16%) Vitamin C 5.4mg (6%) Calcium 66mg (7%) Iron 1.8mg (10%)

Nutrition Facts

Serving: 13cookies

Amount Per Serving

Calories 519

% Daily Value*

Calories 519kcal 26%
Carbohydrates 73g 24%
Protein 4g 8%
Fat 23g 35%
Saturated Fat 14g 70%
Cholesterol 86mg 29%
Sodium 283mg 12%
Potassium 188mg 4%
Fiber 1g 4%
Sugar 49g 98%
Vitamin A 775IU 16%
Vitamin C 5.4mg 6%
Calcium 66mg 7%
Iron 1.8mg 10%

* Percent Daily Values are based on a 2,000 calorie diet.