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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! These soft, gooey rolls are a creative twist on the beloved classic, featuring fluffy dough enveloped in a luscious filling of brown sugar and cinnamon, topped with caramelized pineapple rings and sweet cherries. Perfect for breakfast, brunch, or dessert, these rolls will add a touch of sunshine to any occasion. Enjoy them warm out of the oven or reheat for a delightful treat later. With their impressive presentation and irresistible flavor combination, they are sure to become a favorite in your home.

Ingredients

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  • 3/4 cup water
  • 1/4 cup bread flour
  • 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)
  • 1 teaspoon vanilla bean paste
  • 6 tablespoons unsalted butter (room temperature)
  • 2/3 cup brown sugar (packed)
  • 1/2 cup unsalted butter (room temperature)
  • 2 tablespoons ground cinnamon
  • 1/2 cup brown sugar (packed)
  • 4 tablespoons unsalted butter
  • Pinch fine sea salt
  • 12 pineapple rings (drained and patted dry)
  • 12 maraschino cherries
  • 1 cup powdered sugar
  • 23 tablespoons whole milk
  • 1/2 teaspoon vanilla

Instructions

  1. Prepare the tangzhong by whisking water and bread flour in a saucepan over medium heat until thickened; set aside to cool.
  2. In a stand mixer bowl, combine remaining bread flour, sugar, yeast, and salt. Add cream, milk, egg, vanilla paste, and tangzhong; knead until rough dough forms.
  3. Gradually incorporate butter while mixing until smooth and elastic.
  4. Let the dough rise for 30 minutes after shaping it into a ball.
  5. Make the filling by combining brown sugar with softened butter and cinnamon.
  6. Melt caramel topping ingredients together in a saucepan; set aside.
  7. Line the baking pan with parchment paper and arrange caramel sauce at the bottom; place pineapple rings and cherries on top.
  8. Roll out dough into a rectangle; spread filling evenly and cut into strips.
  9. Roll each strip tightly and place them in the pan over the fruit; let rise for an hour or two until doubled.
  10. Bake at 325°F (162°C) for 35–40 minutes or until cooked through.
  11. Cool slightly before icing and serving.

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