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Pineapple Upside Down Sugar Cookies Recipe

Pineapple Upside Down Sugar Cookies Recipe


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4.6 from 13 reviews

  • Total Time: 35 minutes
  • Yield: 12 1x

Description

Sweet, buttery pineapple upside down sugar cookies blend classic dessert nostalgia with delightful cookie charm. Caramelized pineapple crowns melt-in-your-mouth sugar cookie bases, promising a tropical twist you’ll savor with pure delight.


Ingredients

Scale

Main Ingredients:

  • 12 pineapple slices (from canned)
  • 12 maraschino cherries
  • 1 1/2 cups all-purpose flour
  • 1 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 1/4 cup unsalted butter, melted

Wet Ingredients:

  • 1 large egg
  • 1 teaspoon vanilla extract

Baking and Seasoning Ingredients:

  • 1/3 cup brown sugar
  • 1/4 teaspoon salt
  • 1/4 teaspoon baking soda

Instructions

  1. Prepare the oven at 350°F and create a caramel base by mixing melted butter and brown sugar. Distribute this mixture evenly across each muffin tin compartment.
  2. Carefully place a pineapple slice atop the caramel mixture, then center a maraschino cherry in the middle of each slice.
  3. In a large mixing bowl, thoroughly cream granulated sugar with softened butter until the mixture becomes light and airy. Incorporate the egg and vanilla extract, blending until smooth.
  4. Separately, combine flour, salt, and baking soda using a whisk, ensuring even distribution of dry ingredients.
  5. Gradually fold the dry ingredient mixture into the wet ingredients, stirring until a consistent dough forms.
  6. Shape the cookie dough into small rounds, gently flattening each ball before positioning them directly over the pineapple and cherry in the muffin tin.
  7. Transfer the muffin tin to the preheated oven and bake for 14-16 minutes, watching for a golden-brown color indicating doneness.
  8. After removing from the oven, allow cookies to rest in the tin for 5 minutes, which helps set the caramel and prevents breaking.
  9. Carefully extract the cookies from the tin, inverting them to showcase the beautiful caramelized pineapple topping.

Notes

  • Perfectly caramelize the brown sugar and butter mixture by ensuring even distribution in each muffin tin compartment for a rich, gooey base.
  • Use room temperature ingredients like butter and egg to achieve a smoother, more consistent cookie dough that blends easily and bakes evenly.
  • Prevent sticking by generously greasing the muffin tin or using non-stick cooking spray before adding the pineapple and cherry base.
  • Try alternative fruits like peaches or mandarin oranges for a creative twist on the classic pineapple upside-down cookie, catering to different taste preferences.
  • Prep Time: 20 minutes
  • Cook Time: 15 minutes
  • Category: Desserts, Snacks
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 12
  • Calories: 163 kcal
  • Sugar: 14 g
  • Sodium: 79 mg
  • Fat: 7 g
  • Saturated Fat: 4 g
  • Unsaturated Fat: 3 g
  • Trans Fat: 0 g
  • Carbohydrates: 23 g
  • Fiber: 0.4 g
  • Protein: 1.5 g
  • Cholesterol: 18 mg