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Pineapple Upside-Down Sugar Cookies Recipe

Pineapple Upside-Down Sugar Cookies Recipe


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4.7 from 13 reviews

  • Total Time: 27-30 minutes
  • Yield: 24 1x

Description

Sweet Southern charm meets classic dessert in this Pineapple Upside-Down Sugar Cookies masterpiece. Caramelized pineapple nestled atop buttery sugar cookies brings nostalgic comfort with each delightful bite you’ll savor.


Ingredients

Scale

Main Ingredients:

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 2 1/2 cups all-purpose flour
  • 1 large egg
  • 1 can (20 ounces/567 grams) pineapple slices, drained and cut into small pieces

Topping Ingredients:

  • 1/2 cup unsalted butter, melted
  • 1/2 cup brown sugar, packed
  • Maraschino cherries, halved

Seasoning and Flavoring Ingredients:

  • 1 teaspoon vanilla extract
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt

Instructions

  1. Prepare the muffin tin by setting the oven to 350F (175C). Coat the tin with light grease or place parchment rounds inside each cavity.
  2. Create the caramel base by whisking melted butter and brown sugar until smooth. Distribute approximately one tablespoon of this mixture into each muffin cup.
  3. Strategically arrange pineapple pieces over the brown sugar mixture, then nestle a maraschino cherry half at the center of each cup.
  4. In a spacious mixing bowl, whip softened butter and granulated sugar until the mixture becomes airy and pale.
  5. Incorporate egg and vanilla extract, blending thoroughly until the ingredients are fully integrated.
  6. Separately combine flour, baking powder, and salt through a gentle whisking motion.
  7. Gradually fold the dry ingredients into the butter mixture, working until a tender dough emerges.
  8. Portion roughly 1½ tablespoons of cookie dough into each muffin cup, carefully pressing the dough to cover the pineapple and cherry topping completely.
  9. Transfer the muffin tin to the preheated oven and bake for 12-15 minutes, watching for golden-brown edges.
  10. Allow cookies to rest in the tin for 5 minutes after removing from the oven.
  11. Invert the muffin tin onto a parchment-lined surface or cooling rack to release the cookies.
  12. Serve these delectable treats warm or at room temperature, showcasing the luscious caramelized pineapple topping.

Notes

  • Swap butter with coconut oil for a dairy-free version that maintains rich flavor and tender texture.
  • Use gluten-free flour blend to make these cookies suitable for those with wheat sensitivities, ensuring the same delightful crumbly consistency.
  • Drain pineapple pieces thoroughly to prevent excess moisture from affecting cookie structure and preventing soggy bottoms.
  • Experiment with alternative fruits like peaches or mandarin oranges for unique flavor variations that still complement the sweet sugar cookie base.
  • Prep Time: 15 minutes
  • Cook Time: 12-15 minutes
  • Category: Desserts, Snacks
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 24
  • Calories: 190 kcal
  • Sugar: 12 g
  • Sodium: 90 mg
  • Fat: 9 g
  • Saturated Fat: 5 g
  • Unsaturated Fat: 4 g
  • Trans Fat: 0.1 g
  • Carbohydrates: 26 g
  • Fiber: 1 g
  • Protein: 2 g
  • Cholesterol: 25 mg