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Pineapple Upside Down Cinnamon Rolls Recipe

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★★★★

3.9 from 86 reviews

These Pineapple Upside Down Cinnamon Rolls combine the classic flavors of caramelized pineapple and cinnamon sugar rolls, offering a delicious twist on a traditional favorite with a rich homemade tangzhong dough for extra softness.

Ingredients

Scale

Dough

  • 3/4 cup water
  • 1/4 cup bread flour
  • 3 2/3 cups bread flour (*See notes below for measuring*)
  • 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
  • Tangzhong from above

Filling

  • 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)

Caramel and Topping

  • 4 tablespoons unsalted butter
  • Pinch fine sea salt
  • 12 pineapple rings (drained and patted dry with paper towels to absorb excess moisture)
  • 12 maraschino cherries

Icing

  • 1 cup powdered sugar
  • 2–3 tablespoons whole milk
  • 1/2 teaspoon vanilla

Instructions

  1. Make the tangzhong: In a small saucepan, make the tangzhong by whisking together the water and all-purpose flour. Cook over medium heat, whisking constantly, for 4-5 minutes until the mixture is a paste-like slurry. Scrape it into a bowl and set it aside until ready to use.
  2. Mix dough ingredients: In a stand mixer bowl, mix the flour, sugar, yeast, and salt. Add the cream, milk, egg, vanilla, and tangzhong to the bowl. Knead on low speed with the dough hook for 2 minutes until it forms a rough dough ball.
  3. Knead dough with butter: With the mixer running on low, add the softened butter one tablespoon at a time, letting it fully incorporate before adding more. Then, continue kneading for another 8-10 minutes or until the dough looks smooth and elastic.
  4. Rest dough: Remove the dough from the bowl and pull the sides into the bottom to create a smooth round ball. Place it seam-side down back into the mixing bowl. Cover with plastic wrap and set aside to rest for 30 minutes.
  5. Make filling: While the dough rests, make the filling. In a medium bowl with a spoon or in a mixer bowl, combine the brown sugar, butter, and cinnamon until smooth. Set aside.
  6. Make brown sugar caramel: Melt the sugar, butter, and salt over medium heat until the butter is melted. Whisk vigorously until the butter is emulsified with the sugar. Set it aside while you prepare the pan.
  7. Prepare pan: Line a metal 9×13 baking pan with parchment paper.
  8. Assemble caramel base: Spoon roughly 1/2 tablespoon of the brown sugar caramel on the bottom of the pan in four rows of three. Place a pineapple ring into the caramel in each spot, then press a cherry into the center.
  9. Roll out dough and add filling: Place the rested dough on a lightly floured surface. Roll it out into a 15×21-inch rectangle, with the longest side closest to you. Spread the brown sugar filling across the surface of the dough, leaving a 1/2-inch border clean at the top.
  10. Cut and roll strips: Use a pizza cutter to cut twelve 1 3/4-inch strips. Roll each strip away from you, then place each on a pineapple ring.
  11. Proof rolls: Cover the pan with plastic wrap and set it aside to rise for 1-2 hours or until the rolls double in size. Meanwhile, preheat the oven to 325°F/162°C.
  12. Bake rolls: Bake for 35-40 minutes or until the internal temperature of the center rolls reaches 185°F.
  13. Cool rolls: Once baked, let the rolls cool for 20 minutes while you make the icing.
  14. Make icing: Whisk together the powdered sugar, milk, and vanilla until smooth.
  15. Invert and serve: Line a large baking sheet with parchment paper and set it on top of the baking pan. Carefully flip the pan upside down onto the baking sheet and remove the pan. Drizzle with vanilla icing and enjoy warm!

Notes

  • See notes below for measuring bread flour accurately.

Keywords: pineapple upside down cinnamon rolls, caramel cinnamon rolls, homemade cinnamon rolls, tropical breakfast rolls, sweet yeast rolls

Find it online: https://foodarohub.com/pineapple-upside-down-cinnamon-rolls-recipe/