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Pineapple Upside Down Cinnamon Rolls Recipe

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4.1 from 13 reviews

These Pineapple Upside Down Cinnamon Rolls combine the classic gooey, fluffy cinnamon roll dough with a caramelized topping of pineapple rings, maraschino cherries, and brown sugar. Baked upside down in a buttery caramel base, then flipped to reveal a golden, sticky tropical fruit topping, they make a visually stunning and delicious brunch or dessert treat perfect for summer gatherings.

  • Author: Zara
  • Prep Time: 4 hours
  • Cook Time: 35 minutes
  • Total Time: 4 hours 35 minutes
  • Yield: 12 servings
  • Category: Breakfast, Brunch, Dessert
  • Method: Baking
  • Cuisine: American

Ingredients

For the Tangzhong

  • 3/4 cup (155 g) water
  • 1/4 cup (32 g) bread flour

For the Cinnamon Roll Dough

  • 3 2/3 cups (485 g) bread flour
  • 1/3 cup (66 g) granulated sugar
  • 2 teaspoons (6 g) instant yeast
  • 1 teaspoon (4 g) fine sea salt
  • 1/3 cup (78 g) heavy cream, room temperature
  • 1/3 cup (78 g) whole milk, room temperature
  • 1 large egg (50 g), room temperature
  • 1 teaspoon (4 g) vanilla bean paste
  • Tangzhong from above
  • 6 tablespoons unsalted butter, room temperature

For the Cinnamon Sugar Filling

  • 2/3 cup brown sugar, packed
  • 1/2 cup unsalted butter, room temperature
  • 2 tablespoons ground cinnamon

For the Brown Sugar Caramel Base

  • 1/2 cup brown sugar, packed
  • 4 tablespoons unsalted butter
  • Pinch fine sea salt
  • 12 pineapple rings, drained and patted dry
  • 12 maraschino cherries

For the Vanilla Glaze

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

Instructions

  1. Make the Tangzhong: In a small saucepan, whisk together 3/4 cup water and 1/4 cup bread flour until smooth. Cook over medium heat, whisking constantly, for 4-5 minutes until it thickens into a paste-like slurry. Transfer to a bowl and let it cool to room temperature.
  2. Mix the Dough Ingredients: In a stand mixer bowl, combine 3 2/3 cups bread flour, 1/3 cup granulated sugar, 2 teaspoons instant yeast, and 1 teaspoon fine sea salt. Add the 1/3 cup heavy cream, 1/3 cup whole milk, 1 large egg, 1 teaspoon vanilla bean paste, and the cooled tangzhong. Mix on low speed with the dough hook for 2 minutes to form a rough dough ball.
  3. Knead the Dough: With the mixer still running on low, add 6 tablespoons of softened unsalted butter one tablespoon at a time, allowing each to incorporate fully. After all butter is added, continue kneading for 8-10 minutes until the dough is smooth and elastic.
  4. First Rise: Cover the dough and let it rise in a warm spot until doubled in size, approximately 1.5 to 2 hours.
  5. Prepare the Brown Sugar Caramel Base: In a 9x13 metal pan, melt 4 tablespoons unsalted butter with 1/2 cup packed brown sugar and a pinch of sea salt over medium heat until bubbly and caramelized. Remove from heat and arrange 12 pineapple rings evenly in the pan with a maraschino cherry in the center of each ring.
  6. Roll and Fill the Dough: Turn the risen dough onto a floured surface and roll into a large rectangle roughly 16x20 inches. Spread the cinnamon sugar filling evenly over the dough using 2/3 cup brown sugar mixed with 1/2 cup softened butter and 2 tablespoons cinnamon. Roll the dough tightly from the long edge and cut into 12 equal rolls.
  7. Arrange Rolls in Pan: Place the rolls over the pineapple and caramel base in the pan, spacing slightly apart. Cover and let rise until nearly doubled, about 45 minutes.
  8. Bake: Preheat the oven to 350°F (175°C). Bake the rolls for 30-35 minutes, until golden brown and cooked through.
  9. Invert and Cool: Allow the pan to cool for 5 minutes, then invert it onto a serving platter carefully to reveal the pineapple upside down topping. Let cool slightly before glazing.
  10. Prepare the Vanilla Glaze: Whisk together 1 cup powdered sugar, 2-3 tablespoons milk, and 1/2 teaspoon vanilla until smooth. Drizzle the glaze over the warm rolls before serving.

Notes

  • Use bread flour for best texture and gluten development.
  • Make sure tangzhong is cooled to room temperature before adding to yeast mixture to avoid killing the yeast.
  • Drain pineapple rings well and pat dry to prevent excess moisture from making the rolls soggy.
  • Room temperature dairy and eggs help achieve a smooth dough.
  • Allow enough rising time for fluffy, airy rolls.
  • Use a metal pan for even heat distribution and proper caramelization.
  • Vanilla bean paste can be swapped with vanilla extract if not available.

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