Print

Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls

5 Stars 4 Stars 3 Stars 2 Stars 1 Star

No reviews

Pineapple Upside Down Cinnamon Rolls are a delightful twist on a classic treat that will elevate any brunch or dessert table. These fluffy rolls feature a gooey filling of brown sugar and cinnamon, topped with caramelized pineapple rings and cherries, creating a beautiful presentation that’s as delicious as it is visually stunning. The warm, tropical flavors of pineapple and cherries blend perfectly with the soft, sweet dough, making each bite a heavenly experience. Perfect for sharing with family and friends or enjoying as an indulgent breakfast treat, these rolls are sure to impress!

Ingredients

Scale
  • 3/4 cup water
  • 3 2/3 cups bread flour
  • 1/3 cup granulated sugar
  • 2 teaspoons instant yeast
  • 1 teaspoon fine sea salt
  • 1 large egg (room temperature)
  • 12 pineapple rings (drained)
  • 12 maraschino cherries
  • 1 cup powdered sugar (for icing)
  • 1/3 cup heavy cream (room temperature)
  • 1/3 cup whole milk (room temperature)
  • 1 teaspoon vanilla bean paste
  • 2/3 cup brown sugar (packed)
  • 1/2 cup unsalted butter (room temperature)
  • 2 tablespoons ground cinnamon
  • 4 tablespoons unsalted butter
  • Pinch fine sea salt

Instructions

  1. Make the Tangzhong by whisking water and flour in a saucepan over medium heat until it forms a paste. Set aside.
  2. In a stand mixer, combine flour, sugar, yeast, and salt. Add cream, milk, egg, vanilla bean paste, and Tangzhong; knead into rough dough.
  3. Gradually add softened butter while kneading until smooth and elastic.
  4. Allow dough to rest for 30 minutes before preparing the filling by mixing brown sugar, butter, and cinnamon.
  5. Prepare caramel by melting brown sugar, butter, and salt in another saucepan.
  6. Line a metal baking pan with parchment paper; assemble topping with caramel drizzle, pineapple rings, and cherries.
  7. Roll out the dough into a rectangle; spread filling, cut strips, roll them up, and place in the pan.
  8. Let rise for 1-2 hours; preheat oven to 325°F (162°C) and bake for 35-40 minutes.
  9. Cool slightly before icing with powdered sugar mixed with milk.

Nutrition