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Pineapple Upside-Down Sugar Cookies

These Pineapple Upside-Down Sugar Cookies combine soft, tender cookie dough with a caramelized brown sugar topping, juicy pineapple, and a bright cherry center. They’re buttery, slightly tangy, and beautifully glossy—like mini upside-down cakes in cookie form.
Print Recipe
Prep Time 25 minutes
Cook Time 25 minutes
Total Time 50 minutes
Servings: 13 cookies
Course: Dessert
Cuisine: American
Calories: 320
Ingredients Method Notes

Ingredients
  

  • 1 cup butter unsalted, softened
  • 1.5 cups sugar
  • 2 eggs
  • 2 tsp vanilla extract
  • 0.5 cup sour cream
  • 3 cups all-purpose flour
  • 1 tsp baking powder
  • 1 tsp cornstarch
  • 0.5 tsp salt
  • 13 pineapple slices canned
  • 13 maraschino cherries
  • 0.5 cup butter melted
  • 1 cup brown sugar packed

Method
 

  1. Preheat oven to 350°F and prepare a mini cake or muffin pan.
  2. Cream butter and sugar until light and fluffy.
  3. Mix in eggs, vanilla, and sour cream.
  4. Add flour, baking powder, cornstarch, and salt; mix until just combined.
  5. Mix melted butter and brown sugar, then spoon into each pan cavity.
  6. Place pineapple slice and cherry in each well.
  7. Top with cookie dough and spread evenly.
  8. Bake for 25 minutes until golden and bubbling.
  9. Cool for 10 minutes, then invert onto wax paper.
  10. Let cool completely before serving.

Notes

Flip while still warm so the caramel topping releases cleanly. Best enjoyed within a couple of days for peak texture and flavor.