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Pineapple Upside-Down Sugar Cookies Recipe

Pineapple Upside-Down Sugar Cookies Recipe


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4.7 from 35 reviews

  • Total Time: 30 minutes
  • Yield: 24 1x

Description

Pineapple upside-down sugar cookies deliver a delightful twist on classic dessert nostalgia. Sweet caramelized fruit nestles atop buttery sugar cookies, creating a charming treat reminiscent of traditional cake that will delight your senses.


Ingredients

Scale

Main Ingredients (Cookies):

  • 2 1/2 cups all-purpose flour
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg

Fat and Leavening Agents:

  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 teaspoon vanilla extract

Topping Ingredients:

  • 1 can (8 ounces/226 grams) pineapple slices, drained (reserve juice)
  • 1/4 cup unsalted butter
  • 1/2 cup brown sugar, packed
  • Maraschino cherries (one for each cookie)

Instructions

  1. Prepare the caramel base by melting butter and brown sugar in a saucepan over medium heat, stirring until the mixture transforms into a smooth, glossy liquid.
  2. Carefully distribute the caramel mixture across the prepared baking sheets, creating a thin, even layer in each designated cookie spot.
  3. Arrange pineapple slices strategically on top of the caramel, ensuring each slice sits centered and flat.
  4. Position a vibrant maraschino cherry in the middle of each pineapple slice, creating a classic upside-down cake aesthetic.
  5. Cream softened butter with granulated sugar until the mixture becomes light and airy, developing a fluffy texture that will contribute to the cookie’s delicate structure.
  6. Incorporate egg and vanilla extract into the butter mixture, blending thoroughly to create a uniform consistency.
  7. Whisk together flour, baking powder, baking soda, and salt in a separate bowl, ensuring even distribution of leavening agents.
  8. Gently fold the dry ingredients into the wet mixture, mixing minimally to prevent overworking the dough and maintain a tender crumb.
  9. Delicately spoon cookie dough over each pineapple slice, covering the fruit partially while allowing some decorative elements to peek through.
  10. Transfer the cookie-laden baking sheets into a preheated 350°F oven and bake for 12-15 minutes, watching for edges to turn a delicate golden brown.
  11. Remove from the oven and allow cookies to rest on the baking sheet for 5 minutes, enabling the caramel to set slightly.
  12. Carefully transfer cookies to a wire rack, letting them cool completely to ensure the caramel topping stabilizes and the cookies achieve optimal texture.

Notes

  • Check butter temperature before creaming to ensure smooth, even texture.
  • Use room-temperature ingredients for better cookie consistency and blending.
  • Avoid overmixing cookie dough to prevent tough, dense cookies.
  • Drain pineapple slices thoroughly to prevent excess moisture affecting cookie texture.
  • Rotate baking sheet halfway through cooking for even browning.
  • Experiment with alternative fruits like peaches or cherries for unique variations.
  • Store cookies in an airtight container to maintain freshness for 3-4 days.
  • For gluten-free option, substitute all-purpose flour with almond or gluten-free blend.
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Category: Desserts, Snacks
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 24
  • Calories: 170
  • Sugar: 12 g
  • Sodium: 150 mg
  • Fat: 7 g
  • Saturated Fat: 4 g
  • Unsaturated Fat: 2 g
  • Trans Fat: 0 g
  • Carbohydrates: 24 g
  • Fiber: 0 g
  • Protein: 1 g
  • Cholesterol: 20 mg