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Pineapple Upside-Down Sugar Cookies

These pineapple upside-down sugar cookies feature a chewy vanilla base topped with caramelized pineapple and optional cherries. A nostalgic twist on a tropical classic and easily adaptable for gluten-free or dairy-free diets.

  • Total Time: 34 minutes
  • Yield: 12–16 cookies (depending on size) 1x

Ingredients

Scale

For the Cookie Dough:

  • ¾ cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 egg
  • 1½ tsp vanilla extract
  • 2 cups all-purpose flour
  • ½ tsp baking powder
  • ½ tsp baking soda
  • ¼ tsp salt

For the Topping:

  • ½ cup light brown sugar
  • 3 tbsp melted butter
  • Pineapple rings (fresh or canned, well-drained)
  • Maraschino cherries (optional)

Instructions

  1. Preheat oven to 350°F (175°C). Line baking tray with parchment.
  2. Cream butter and sugar. Add egg and vanilla.
  3. Mix dry ingredients and combine with wet to form soft dough.
  4. In a small bowl, mix melted butter and brown sugar. Spoon onto tray in small circles.
  5. Place pineapple and cherry on top of the sugar.
  6. Flatten dough balls and place over fruit.
  7. Bake for 12–14 minutes until golden. Let cool slightly, then flip cookies to reveal pineapple topping.
  • Author: Tom
  • Prep Time: 20 minutes
  • Cook Time: 14 minutes
  • Category: Cookies, Dessert, Fruit-Based
  • Method: Baking, Flip Technique
  • Cuisine: American, Tropical-Inspired
  • Diet: Vegetarian

Keywords: pineapple upside-down sugar cookies, tropical sugar cookies, fruity cookie recipe, caramelized pineapple cookies, no alcohol cookies

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