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Pineapple Upside-Down Sugar Cookies Recipe

Pineapple Upside-Down Sugar Cookies Recipe


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4.8 from 14 reviews

  • Total Time: 30 minutes
  • Yield: 12 1x

Description

Tropical paradise meets classic dessert in these irresistible Pineapple Upside-Down Sugar Cookies that blend sweet caramelized pineapple with buttery cookie perfection. Sweet nostalgia and island charm create a delightful treat you’ll savor with each delectable bite.


Ingredients

Scale

Main Ingredients:

  • 1 can or 68 fresh pineapple rings
  • ½ cup unsalted butter
  • ½ cup brown sugar

Flour and Dry Ingredients:

  • 1 ½ cups all-purpose flour
  • 1 teaspoon (5 grams) baking powder
  • ¼ teaspoon salt

Cookie Wet Ingredients:

  • ½ cup unsalted butter, softened
  • ½ cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 46 maraschino cherries

Instructions

  1. Prepare the oven environment by warming it to 350F (175C) and thoroughly coating a muffin tin with non-stick spray to prevent potential sticking.
  2. Create a rich caramel-like base by whisking melted butter and brown sugar until smooth and well-combined.
  3. Distribute the butter-sugar mixture evenly across the muffin tin, carefully spooning approximately one teaspoon into each individual cup.
  4. Artfully place pineapple chunks and halved cherries at the bottom of each prepared muffin cavity, ensuring attractive positioning and complete coverage.
  5. Position the tin strategically in the preheated oven, allowing the sugary mixture to caramelize and infuse the fruit with deep, golden undertones.
  6. Monitor the baking process closely, watching for the edges to turn golden brown and the fruit to become slightly translucent and glossy.
  7. Once baked, remove from the oven and let the cookies rest momentarily, allowing the caramelized fruit to set and develop a rich, complex flavor profile.
  8. Carefully invert the muffin tin onto a serving platter, gently tapping to release the cookies, revealing the beautifully caramelized fruit topping.
  9. Allow the upside-down cookies to cool completely, ensuring the caramel and fruit remain perfectly adhered to the cookie base.

Notes

  • Caramelize the brown sugar and butter mixture gently to prevent burning, creating a rich, golden base for the cookies.
  • Arrange pineapple chunks and cherries with care, ensuring even distribution and an aesthetically pleasing presentation.
  • For a gluten-free version, substitute all-purpose flour with a 1:1 gluten-free baking blend to maintain the cookie’s soft texture.
  • Experiment with alternative fruits like peaches or apricots to create unique flavor variations while keeping the classic upside-down cookie concept.
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Category: Desserts, Snacks
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 12
  • Calories: 150
  • Sugar: 10 g
  • Sodium: 150 mg
  • Fat: 7 g
  • Saturated Fat: 4 g
  • Unsaturated Fat: 2 g
  • Trans Fat: 0 g
  • Carbohydrates: 20 g
  • Fiber: 1 g
  • Protein: 2 g
  • Cholesterol: 30 mg