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Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls

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Pineapple Upside Down Cinnamon Rolls are a delightful twist on a classic favorite, combining fluffy dough with caramelized pineapple and cherries for an irresistible treat. Perfect for breakfast or brunch gatherings, these rolls capture the essence of summer with their tropical flavors and gooey sweetness. Impress your guests with their stunning upside-down presentation and enjoy the fun of making them together with family or friends.

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
  • 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. Make the Tangzhong: Whisk water and bread flour in a saucepan over medium heat until a paste forms, about 4–5 minutes. Let cool.
  2. Prepare the Dough: In a stand mixer, combine bread flour, sugar, yeast, and salt. Add heavy cream, milk, egg, vanilla, and cooled tangzhong. Knead on low speed until rough dough forms.
  3. Incorporate Butter: Gradually add softened butter while mixing until fully incorporated. Knead until smooth and elastic.
  4. Let Dough Rise: Shape into a ball, cover with plastic wrap, and let rise for 30 minutes.
  5. Make Filling: Blend brown sugar, softened butter, and cinnamon until smooth.
  6. Prepare Caramel Base: Melt brown sugar, butter, and salt in a saucepan until combined.
  7. Assemble in Baking Pan: Line pan with parchment paper; layer caramel mixture followed by pineapple rings and cherries.
  8. Roll Out Dough: Roll out dough into a rectangle; spread filling evenly across it.
  9. Cut and Roll Cinnamon Rolls: Slice into strips; roll each tightly and place over prepared fruit in the pan.
  10. Second Rise: Cover and let rise for 1–2 hours until doubled in size.
  11. Bake: Preheat oven to 325°F (162°C) and bake for 35–40 minutes until internal temperature reaches 185°F.
  12. Cool & Ice: Allow cooling before icing with a mixture of powdered sugar, milk, and vanilla.

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