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Sweet Pineapple Upside-Down Sugar Cookies Recipe

Sweet Pineapple Upside-Down Sugar Cookies Recipe


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4.7 from 37 reviews

  • Total Time: 30 minutes
  • Yield: 11 1x

Description

Delightful pineapple upside-down sugar cookies blend classic cake nostalgia with cookie charm. Sweet caramelized pineapple tops crisp, buttery cookies that will transport you directly to dessert paradise.


Ingredients

Scale
  • 1 can pineapple rings (fresh or canned)
  • ½ cup maraschino cherries
  • ½ cup (113 g) unsalted butter
  • ½ cup brown sugar
  • 2 cups (240 g) all-purpose flour
  • ¾ cup (150 g) granulated sugar
  • ½ cup (113 g) unsalted butter, softened
  • 1 large egg
  • 1 tsp vanilla extract
  • 1 tsp baking powder
  • ¼ tsp salt

Instructions

  1. Muffin Tin Preparation: Lavishly coat each cavity with non-stick spray, ensuring seamless cookie extraction without sticking.
  2. Caramel Foundation: Whisk melted butter and brown sugar into a silky, luminous mixture that promises decadent flavor depth for the cookies.
  3. Fruit Placement: Meticulously arrange pineapple chunks and maraschino cherries in an artistic pattern, positioning each piece precisely against the muffin cup walls to create a stunning visual landscape when ultimately inverted.
  4. Dough Application: Gently layer cookie dough over the fruit base, delicately distributing the mixture to preserve the intricate tropical arrangement underneath, ensuring complete coverage without disrupting the carefully curated design.
  5. Baking Process: Heat oven to the specified temperature, allowing the cookies to transform, with caramel bubbling and fruit caramelizing while the dough bakes to golden perfection, creating a harmonious blend of textures and flavors.
  6. Final Presentation: Once baked, immediately invert the muffin tin onto a serving platter, allowing the cookies to reveal their gorgeous pineapple-topped masterpiece, with caramelized fruit glistening against the tender cookie base.

Notes

  • Prep Pan Perfectly: Generously spray muffin tin with non-stick cooking spray to guarantee seamless cookie removal without sticking or breaking.
  • Master Caramel Layer: Whisk melted butter and brown sugar thoroughly until silky smooth, ensuring complete sugar dissolution for rich, even caramelization.
  • Fruit Placement Strategy: Arrange pineapple chunks and cherries with precision, pressing gently against tin walls to create an attractive, professional-looking design when cookies are flipped.
  • Gentle Dough Application: Carefully spoon cookie dough over fruit layer without disrupting the carefully crafted tropical arrangement, maintaining the decorative bottom design.
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Category: Desserts, Snacks
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 11
  • Calories: 210
  • Sugar: 15 g
  • Sodium: 150 mg
  • Fat: 10 g
  • Saturated Fat: 6 g
  • Unsaturated Fat: 4 g
  • Trans Fat: 0 g
  • Carbohydrates: 30 g
  • Fiber: 1 g
  • Protein: 2 g
  • Cholesterol: 25 mg