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Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls

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Indulge in the tropical delight of Pineapple Upside Down Cinnamon Rolls, a unique twist on the beloved classic. These rolls feature fluffy dough enveloping a gooey filling of caramelized pineapple and sweet cherries, all topped with a luscious brown sugar glaze. Perfect for brunch or dessert, they not only taste amazing but also present beautifully when flipped to showcase their golden, sticky topping. With straightforward steps and simple ingredients, this recipe is accessible for bakers of all skill levels. Serve warm for an unforgettable treat that will transport your taste buds to paradise.

  • Total Time: 1 hour 10 minutes
  • Yield: Serves 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 (room temperature)
  • 1/3 cup whole milk (room temperature)
  • 1 large egg (room temperature)
  • 12 pineapple rings (drained and patted dry)
  • 12 maraschino cherries
  • For icing: 1 cup powdered sugar, 2–3 tablespoons whole milk, 1/2 teaspoon vanilla

Instructions

  1. Make the tangzhong by whisking together water and bread flour in a saucepan over medium heat until thickened. Set aside.
  2. In a stand mixer bowl, combine remaining bread flour, sugar, yeast, and salt. Add cream, milk, egg, vanilla bean paste, and tangzhong; knead until a rough ball forms.
  3. Gradually add softened butter while mixing until smooth and elastic. Let rise covered until doubled in size.
  4. Prepare the filling by mixing brown sugar, softened butter, and cinnamon in a bowl.
  5. Make the caramel topping by melting butter with brown sugar and salt on medium heat; set aside.
  6. Line a baking pan with parchment paper and assemble rolls by placing pineapple rings and cherries into the caramel mix.
  7. Roll out dough into a rectangle; spread filling evenly and cut into strips to form rolls.
  8. Arrange rolls over fruit in the pan; let rise again before baking at 325°F (162°C) for about 35–40 minutes.
  9. Allow to cool slightly before flipping onto a serving plate and drizzling with icing.
  • Author: Jennifer Carter
  • Prep Time: 30 minutes
  • Cook Time: 40 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: Tropical

Nutrition

  • Serving Size: 1 roll (90g)
  • Calories: 290
  • Sugar: 20g
  • Sodium: 165mg
  • Fat: 8g
  • Saturated Fat: 5g
  • Unsaturated Fat: 2g
  • Trans Fat: 0g
  • Carbohydrates: 50g
  • Fiber: 2g
  • Protein: 4g
  • Cholesterol: 30mg