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Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls

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Indulge in the delightful taste of Pineapple Upside Down Cinnamon Rolls, a tropical twist on a classic favorite. These soft, fluffy rolls are topped with caramelized pineapple and cherries, creating an eye-catching and delicious dessert perfect for any occasion. Whether you’re hosting a brunch or treating yourself to a sweet snack, these rolls are sure to impress with their stunning presentation and irresistible flavor. Made from scratch using simple ingredients, this recipe is not only enjoyable to make but also customizable to suit your taste preferences. Experience the joy of baking with this unique and flavorful treat!

  • Total Time: 1 hour 20 minutes
  • Yield: Makes approximately 12 rolls 1x

Ingredients

Scale
  • 3/4 cup water
  • 3 2/3 cups bread flour
  • 1/3 cup granulated sugar
  • 2 teaspoons instant yeast
  • 1 teaspoon fine sea salt
  • 1/3 cup heavy cream
  • 1/3 cup whole milk
  • 1 large egg
  • 12 pineapple rings (drained)
  • 12 maraschino cherries
  • For the icing: powdered sugar, whole milk, vanilla
  • 6 tablespoons unsalted butter (for filling)
  • 2/3 cup brown sugar (for filling)
  • 2 tablespoons ground cinnamon (for filling)
  • 4 tablespoons unsalted butter (for caramel)
  • Pinch fine sea salt (for caramel)
  • 1/2 cup brown sugar (for caramel)

Instructions

  1. Prepare tangzhong by whisking water and flour in a saucepan over medium heat until it thickens.
  2. In a stand mixer bowl, combine flour, sugar, yeast, and salt; add cream, milk, egg, vanilla, and tangzhong.
  3. Knead until smooth; incorporate softened butter gradually.
  4. Let the dough rest for about 30 minutes.
  5. Mix brown sugar, butter, and cinnamon for filling; melt butter with brown sugar and salt for caramel topping.
  6. Prepare a baking pan by layering caramel mixture with pineapple rings and cherries.
  7. Roll out dough into a rectangle; spread filling and cut into strips.
  8. Roll each strip tightly and place them in the prepared pan; let rise again for about an hour.
  9. Bake at 325°F for 35–40 minutes until golden brown; cool slightly before icing.
  • Author: Sarah DuRoss
  • Prep Time: 40 minutes
  • Cook Time: 40 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: Tropical

Nutrition

  • Serving Size: 1 roll
  • Calories: 280
  • Sugar: 18g
  • Sodium: 220mg
  • Fat: 10g
  • Saturated Fat: 6g
  • Unsaturated Fat: 4g
  • Trans Fat: 0g
  • Carbohydrates: 42g
  • Fiber: 2g
  • Protein: 5g
  • Cholesterol: 30mg