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–+ servings
Pineapple rolls on a baking sheet.
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Pineapple Upside Down Cinnamon Rolls

These pineapple upside down cinnamon rolls combine gooey, fluffy dough with caramelized pineapple, cherries, and brown sugar for a tropical twist on the classic. Baked upside down, then flipped to reveal that golden, sticky fruit topping...they're a summer showstopper!

Equipment

  • metal 9x13 pan

Ingredients

For the Tangzhong

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

For the Cinnamon Roll 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

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 with paper towels to absorb excess moisture
  • 12 maraschino cherries

For the Vanilla Glaze

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

Instructions

  • In a small saucepan, make the tangzhong by whisking together the water and all-purpose flour. Cook over medium heat, whisking constantly, for 4-5 minutes until the mixture is a paste-like slurry. Scrape it into a bowl and set it aside until ready to use.
  • In a stand mixer bowl, mix the flour, sugar, yeast, and salt. Add the cream, milk, egg, vanilla, and tangzhong to the bowl. Knead on low speed with the dough hook for 2 minutes until it forms a rough dough ball.
  • With the mixer running on low, add the softened butter one tablespoon at a time, letting it fully incorporate before adding more. Then, continue kneading for another 8-10 minutes or until the dough looks smooth and elastic.
  • Remove the dough from the bowl and pull the sides into the bottom to create a smooth round ball. Place it seam-side down back into the mixing bowl. Cover with plastic wrap and set aside to rest for 30 minutes.
  • While the dough rests, make the filling. In a medium bowl with a spoon or in a mixer bowl, combine the brown sugar, butter, and cinnamon until smooth. Set aside.
  • Make the brown sugar caramel. Melt the sugar, butter, and salt over medium heat until the butter is melted. Whisk vigorously until the butter is emulsified with the sugar. Set it aside while you prepare the pan.
  • Line a metal 9x13 baking pan with parchment paper.
  • Spoon roughly 1/2 tablespoon of the brown sugar caramel on the bottom of the pan in four rows of three. Place a pineapple ring into the caramel in each spot, then press a cherry into the center.
  • Place the rested dough on a lightly floured surface. Roll it out into a 15x21-inch rectangle, with the longest side closest to you. Spread the brown sugar filling across the surface of the dough, leaving a 1/2-inch border clean at the top.
  • Use a pizza cutter to cut twelve 1 3/4-inch strips. Roll each strip away from you, then place each on a pineapple ring.
  • Cover the pan with plastic wrap and set it aside to rise for 1-2 hours or until the rolls double in size. Meanwhile, preheat the oven to 325°F/162°C.
  • Bake for 35-40 minutes or until the internal temperature of the center rolls reaches 185°F.
  • Once baked, let the rolls cool for 20 minutes while you make the icing.
  • Whisk together the powdered sugar, milk, and vanilla until smooth.
  • Line a large baking sheet with parchment paper and set it on top of the baking pan. Carefully flip the pan upside down onto the baking sheet and remove the pan. Drizzle with vanilla icing and enjoy warm!

Notes

*Measure your dry ingredients properly. This is my #1 baking tip! Do not ever scoop a measuring cup into your flour, as this always leads to using too much flour. Instead, use the spoon-level method. This means fluffing the flour first, then spooning it into your measuring cup/spoon. For the BEST results, use a kitchen scale!*
Storage: Leftover rolls can be stored in an airtight container in the fridge for up to 4 days. They can be reheated in a 350°F oven or in the microwave in 20-second increments. *To prevent the rolls from becoming stale, leave a wet paper towel in the container, not touching the rolls, to maintain moisture.*
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