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Pineapple Upside Down Cinnamon Rolls Recipe

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★★★★

3.8 from 90 reviews

These Pineapple Upside Down Cinnamon Rolls combine the classic tropical pineapple upside down cake with soft, cinnamon-spiced rolls. Featuring a sticky brown sugar caramel base topped with juicy pineapple rings and maraschino cherries, these rolls are soft, sweet, and perfect for a special breakfast or brunch. Made with a tangzhong-enhanced dough for extra softness and topped with a vanilla glaze, they deliver a delightful balance of fruity, buttery, and cinnamon flavors.

Ingredients

Scale

Dough Ingredients

  • 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
  • Tangzhong from above (made with water and all-purpose flour)

Filling Ingredients

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

Caramel Ingredients

  • 1/2 cup unsalted butter (room temperature)
  • 2/3 cup brown sugar (packed)
  • Pinch fine sea salt

Topping Ingredients

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

Icing Ingredients

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

Instructions

  1. Make the tangzhong: In a small saucepan, whisk together 3/4 cup water and 1/4 cup bread flour over medium heat. Stir constantly for 4-5 minutes until the mixture thickens to a paste-like slurry. Transfer to a bowl and let cool.
  2. Prepare dough mixture: 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 1/3 cup heavy cream, 1/3 cup whole milk, 1 large room temperature egg, 1 teaspoon vanilla bean paste, and the cooled tangzhong. Knead on low speed with dough hook for 2 minutes until a rough dough ball forms.
  3. Incorporate butter and knead: While mixer runs on low, add 6 tablespoons softened unsalted butter one tablespoon at a time, fully integrating each before adding more. Continue kneading for 8-10 minutes until dough is smooth and elastic.
  4. First dough rise: Remove dough and shape into a smooth ball pulling sides underneath. Place seam-side down in mixing bowl and cover with plastic wrap. Let rest for 30 minutes.
  5. Prepare cinnamon filling: In a bowl, mix 2/3 cup packed brown sugar, 2 tablespoons ground cinnamon, and 6 tablespoons softened butter until smooth. Set aside.
  6. Make brown sugar caramel: In a saucepan, melt 1/2 cup butter with 2/3 cup brown sugar and a pinch of fine sea salt over medium heat. Whisk vigorously until butter and sugar emulsify. Set aside.
  7. Prepare baking pan: Line a 9×13 inch metal baking pan with parchment paper. Spoon about 1/2 tablespoon caramel in 12 spots in a 4×3 grid. Place a pineapple ring over each caramel spot and press a maraschino cherry into the center of each pineapple ring.
  8. Roll out dough: On a lightly floured surface, roll the rested dough into a 15×21 inch rectangle with the long side toward you. Spread the cinnamon filling evenly over the dough, leaving a 1/2 inch border on top edge clean.
  9. Cut and roll strips: Use a pizza cutter to slice dough into twelve 1 3/4 inch strips. Roll each strip away from you tightly and place each roll on top of a pineapple ring in the caramel-lined pan.
  10. Second rise: Cover the pan with plastic wrap and let the rolls rise for 1-2 hours or until doubled in size. Meanwhile, preheat oven to 325°F (162°C).
  11. Bake: Bake rolls for 35-40 minutes until golden and internal temperature reaches 185°F.
  12. Cool and prepare icing: Let rolls cool for 20 minutes. Meanwhile, whisk 1 cup powdered sugar, 2-3 tablespoons whole milk, and 1/2 teaspoon vanilla together until smooth.
  13. Invert and serve: Place a parchment-lined baking sheet over the pan and carefully flip the pan upside down onto the sheet. Remove the pan and drizzle rolls with vanilla icing. Serve warm for best enjoyment.

Notes

  • Measuring bread flour accurately is important for dough texture; spoon and level rather than scooping.
  • Ensure pineapple rings are well drained and patted dry to prevent soggy rolls.
  • Tangzhong method helps create a soft, fluffy dough with longer freshness.
  • The rolls can be stored covered at room temperature and gently reheated before serving.
  • If you don’t have a stand mixer, knead the dough by hand but expect longer kneading time.

Keywords: pineapple upside down cinnamon rolls, cinnamon rolls, pineapple rolls, breakfast rolls, caramel cinnamon rolls, sweet rolls, brunch recipe

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