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Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls

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Indulge in the delightful flavors of Pineapple Upside Down Cinnamon Rolls, a tropical twist on the classic cinnamon roll. These fluffy rolls are topped with caramelized pineapple and cherries, resulting in a beautiful presentation that is sure to impress at any gathering. Perfect for breakfast, brunch, or dessert, they combine sweet fruit with warm cinnamon, creating an irresistible flavor profile that everyone will love. Whether you’re hosting a summer brunch or enjoying a cozy winter morning, these rolls bring joy to any occasion.

  • Total Time: 1 hour 25 minutes
  • Yield: Makes about 12 servings 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
  • 4 tablespoons unsalted butter (for topping)
  • 12 pineapple rings (drained)
  • 12 maraschino cherries
  • 1 cup powdered sugar (for icing)

Instructions

  1. Prepare the tangzhong by whisking water and flour in a saucepan over medium heat until thickened. Let cool.
  2. In a stand mixer, combine bread flour, sugar, yeast, and salt. Add cream, milk, egg, vanilla, and cooled tangzhong; knead to form dough.
  3. Gradually incorporate softened butter until smooth and elastic.
  4. Let dough rise for 30 minutes covered with plastic wrap.
  5. For filling: mix brown sugar, cinnamon, and butter until smooth.
  6. For caramel topping: melt butter with brown sugar and salt; set aside.
  7. Assemble by layering caramel in a baking pan followed by pineapple rings and cherries.
  8. Roll out dough into a rectangle; spread filling evenly before cutting into strips and rolling into shapes.
  9. Place rolls on top of the fruit layer; let rise for another hour or two.
  10. Bake at 325°F (162°C) for 35-40 minutes until golden brown.
  11. Cool slightly before flipping onto a serving platter and drizzling with icing.
  • Author: Amanda
  • Prep Time: 45 minutes
  • Cook Time: 40 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: Tropical

Nutrition

  • Serving Size: 1 serving
  • Calories: 340
  • Sugar: 20g
  • Sodium: 280mg
  • Fat: 14g
  • Saturated Fat: 8g
  • Unsaturated Fat: 5g
  • Trans Fat: 0g
  • Carbohydrates: 49g
  • Fiber: 2g
  • Protein: 4g
  • Cholesterol: 50mg
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