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pineapple upside down cookies
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Pineapple Upside Down Sugar Cookies

These pineapple upside down sugar cookies are one of the most fun desserts I’ve made in a long time.
Prep Time15 minutes
Cook Time15 minutes
Total Time30 minutes
Course: Dessert
Cuisine: American
Servings: 9 cookies
Calories: 328kcal
Author: Geraldine Julie

Ingredients

For the Topping

  • 9 small pineapple rings (or cut standard rings into smaller circles)
  • ¼ cup dark brown sugar
  • 3 tablespoon unsalted butter, melted
  • 9 maraschino cherries (optional)

The Cookie Base

  • ½ cup unsalted butter, softened
  • ½ cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1¼ cups all-purpose flour
  • ½ teaspoon baking powder
  • ¼ teaspoon salt
  • 2 tablespoon pineapple jam
  • 2 tablespoon heavy cream

Instructions

  • Lay the pineapple rings on paper towels and press gently to remove excess moisture.
  • Preheat the oven to 350°F (175°C) and line a baking sheet or pan with parchment paper.
  • In a small bowl, mix melted butter and brown sugar. Spoon small circles onto the baking sheet.
  • Place pineapple rings over the sugar mixture and add cherries in the centers if using.
  • In a bowl, beat butter and sugar until creamy. Add egg and vanilla extract.
  • Mix in the dry ingredients, flour, baking powder, and ¼ teaspoon salt until crumbly.
  • Stir together pineapple jam and heavy cream, then add to the cookie dough.
  • Shape dough into balls, flatten slightly, and place over the pineapple rings.
  • Bake for 15–18 minutes until they are golden.
  • Let the cookies rest for exactly 4 minutes, then carefully flip them over. You can add a cherry to the tops of these cookies.

Video

Notes

Cooking Time and Temperature

Bake at 350°F (175°C) for 15–18 minutes until golden and bubbling around the edges.

Taste & Texture

Soft buttery cookies with juicy caramelized pineapple and a glossy sweet topping.

Storage, Freezing & Reheating

  • Fridge: Store up to 3 days in an airtight container.
  • Freezer: Freeze for up to 2 months.
  • Best Served: Slightly warm or at room temperature.

Serving Recommendations

I love serving these slightly warm with vanilla ice cream. The caramelized pineapple tastes incredible with something cold and creamy.

Recipe Variations and Substitutions

  • Add a splash of dark rum to the caramel.
  • Use Amarena cherries for a more elegant look.
  • Add toasted coconut on top after baking.

Proper Storage Tips

  • Store in a single layer if possible.
  • Keep refrigerated because of the fruit topping.
  • Warm slightly before serving for the best texture.

Pro Tips

  • Dry the pineapple well.
  • Use parchment paper.
  • Flip while the caramel is still tacky.

Nutrition

Calories: 328kcal | Carbohydrates: 45g | Protein: 3g | Fat: 16g | Saturated Fat: 10g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 4g | Trans Fat: 1g | Cholesterol: 59mg | Sodium: 79mg | Potassium: 139mg | Fiber: 1g | Sugar: 29g | Vitamin A: 538IU | Vitamin C: 6mg | Calcium: 39mg | Iron: 1mg