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Pineapple Upside Down Cinnamon Rolls Recipe

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4.3 from 54 reviews

These Pineapple Upside Down Cinnamon Rolls are a delightful twist on classic cinnamon rolls, featuring a tangzhong-enriched dough for extra softness, a rich brown sugar caramel with pineapple rings and maraschino cherries baked on the bottom, and a creamy vanilla icing drizzle on top. Perfect for a special breakfast or brunch, these rolls are as visually stunning as they are delicious.

  • Total Time: 4 hours 35 minutes
  • Yield: 12 servings

Ingredients

Dough (Tangzhong)

  • 2/3 cup water
  • 1/4 cup bread flour

Dough

  • 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)
  • 6 tablespoons unsalted butter (room temperature)

Brown Sugar Filling

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

Brown Sugar Caramel

  • 4 tablespoons unsalted butter
  • 2/3 cup brown sugar (packed)
  • Pinch fine sea salt

Toppings

  • 12 pineapple rings (drained and patted dry)
  • 12 maraschino cherries

Vanilla Icing

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

Instructions

  1. Make the Tangzhong: In a small saucepan, whisk together 2/3 cup water and 1/4 cup bread flour. Cook over medium heat, whisking constantly for 4-5 minutes until it turns into a thick paste-like slurry. Scrape into a bowl and let it cool until ready to use.
  2. Mix Dry Ingredients: In a stand mixer bowl, combine 3 2/3 cups bread flour, granulated sugar, instant yeast, and salt.
  3. Add Wet Ingredients and Tangzhong: Add heavy cream, whole milk, egg, vanilla bean paste, and the cooled tangzhong to the dry ingredients. Knead with the dough hook on low speed for 2 minutes until a rough dough forms.
  4. Incorporate Butter: With the mixer on low, add softened butter one tablespoon at a time, allowing each to incorporate fully before adding more. Continue kneading for 8-10 minutes until the dough becomes smooth and elastic.
  5. First Dough Rise: Remove dough and shape into a smooth round ball, pull sides underneath. Place seam-side down in a bowl, cover with plastic wrap, and rest for 30 minutes.
  6. Make Brown Sugar Filling: In a medium bowl, mix 2/3 cup brown sugar, 1/2 cup butter, and cinnamon until smooth and well combined. Set aside.
  7. Prepare Brown Sugar Caramel: Melt 4 tablespoons unsalted butter, 2/3 cup brown sugar, and a pinch of salt over medium heat, whisk vigorously until the mixture emulsifies and is smooth. Set aside.
  8. Prepare Baking Pan: Line a 9×13 inch metal baking pan with parchment paper. Spoon about 1/2 tablespoon caramel into the pan in four rows of three spots. Place a pineapple ring on each caramel spot and press a maraschino cherry into the center of each ring.
  9. Roll Out Dough: On a floured surface, roll the rested dough into a 15×21 inch rectangle with the longest side facing you. Spread the brown sugar filling evenly, leaving a 1/2 inch border at the top edge.
  10. Cut and Roll the Dough: Cut twelve 1 3/4-inch strips using a pizza cutter. Roll each strip tightly away from you into a spiral. Place each roll on top of a pineapple ring in the pan.
  11. Second Rise: Cover the pan with plastic wrap and let the rolls rise for 1-2 hours or until doubled in size. Meanwhile, preheat the oven to 325°F (162°C).
  12. Bake the Rolls: Bake for 35-40 minutes or until the internal temperature of the center rolls reaches 185°F and the rolls are golden brown.
  13. Cool Rolls: Let the rolls cool in the pan for 20 minutes to set before flipping.
  14. Make the Vanilla Icing: Whisk together powdered sugar, whole milk (start with 2 tablespoons), and vanilla until smooth and pourable. Adjust milk quantity to desired consistency.
  15. Invert and Serve: Place a large baking sheet lined with parchment paper on top of the pan. Carefully flip the pan upside down onto the sheet and remove the pan to reveal the pineapple upside down cinnamon rolls. Drizzle with vanilla icing and serve warm.

Notes

  • When measuring bread flour, spoon the flour into the measuring cup and level off with a knife instead of scooping directly to avoid packed flour and ensure accuracy.
  • Allowing ingredients like cream, milk, and egg to come to room temperature ensures better dough formation and yeast activation.
  • Make sure pineapple rings are well-drained and patted dry to prevent too much moisture in the caramel layer.
  • Using tangzhong enhances the softness and keeps the rolls fresh longer.
  • For best results, monitor the internal temperature of rolls with a probe thermometer to avoid underbaking or drying them out.
  • Author: Madelynn
  • Prep Time: 30 minutes
  • Cook Time: 40 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

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