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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 fusion of tropical flavors and classic sweet rolls that will brighten any breakfast or brunch table. These fluffy, gooey treats feature a luscious filling of brown sugar and cinnamon, complemented by caramelized pineapple rings and cherries. The upside-down baking technique transforms the rolls into a stunning presentation, making them not only delicious but also visually impressive. Perfect for sharing with family and friends, this recipe is a fun kitchen project that guarantees smiles all around. Indulge in the taste of summer with every bite, no matter the season!

Ingredients

Scale
  • 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
  • 1/2 cup brown sugar (packed)
  • 4 tablespoons unsalted butter
  • Pinch fine sea salt
  • 12 pineapple rings (drained and patted dry)
  • 12 maraschino cherries
  • 1 cup powdered sugar
  • 2–3 tablespoons whole milk
  • 1/2 teaspoon vanilla

Instructions

  1. Make the Tangzhong: Whisk water and flour in a saucepan over medium heat until thickened; let cool.
  2. Prepare Dough: Combine bread flour, sugar, yeast, salt, cream, milk, egg, vanilla bean paste, and cooled Tangzhong in a stand mixer; mix until rough dough forms.
  3. Knead Dough: Gradually add butter while mixing; knead for 8–10 minutes until smooth and elastic.
  4. First Rise: Shape dough into a ball, place in greased bowl, cover with plastic wrap, and let rise for 30 minutes.
  5. Prepare Filling: Mix together butter, brown sugar, and cinnamon until smooth.
  6. Make Caramel: Melt brown sugar with butter and a pinch of salt in a saucepan until combined.
  7. Assemble: Line a pan with parchment paper; add caramel at the bottom followed by pineapple rings and cherries.
  8. Roll Out Dough: Roll dough into a rectangle; spread with cinnamon filling; cut into strips and roll up.
  9. Second Rise: Place rolls on top of pineapple arrangement; cover and let rise for 1–2 hours until doubled.
  10. Bake: Preheat oven to 325°F (162°C); bake for 35–40 minutes until golden brown.
  11. Cool & Ice: Let cool slightly before flipping onto serving dish; drizzle with icing made from powdered sugar, milk, and vanilla.

Nutrition

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