Pineapple Upside Down Cinnamon Rolls Recipe

Ingredients

Tangzhong

• 2/3 cup water
• 1/4 cup bread flour

Cinnamon Roll Dough

• 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
• 6 tablespoons unsalted butter, room temperature

Cinnamon Sugar Filling

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

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
• 12 maraschino cherries

Vanilla Glaze

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

Instructions

1. In a small saucepan, whisk together 2/3 cup water and 1/4 cup bread flour. Cook over medium heat, whisking constantly for 5 minutes until it becomes a thick paste. Scrape into a bowl and let it cool until ready to use.
2. In a stand mixer bowl, combine 3 2/3 cups bread flour, 1/3 cup granulated sugar, 2 teaspoons instant yeast, and 1 teaspoon sea salt. Add 1/3 cup heavy cream, 1/3 cup whole milk, 1 large egg, 1 teaspoon vanilla bean paste, and the tangzhong. Knead on low speed with a dough hook for 2 minutes until a rough dough forms.
3. With the mixer running on low, add 6 tablespoons softened butter one tablespoon at a time, allowing full incorporation. Continue kneading for 10 minutes until the dough is smooth and elastic.
4. Remove dough, shape it into a smooth ball with seams tucked underneath, place seam-side down in the bowl, cover with plastic wrap, and let rest for 30 minutes.
5. In a medium bowl, mix 2/3 cup brown sugar, 1/2 cup softened unsalted butter, and 2 tablespoons ground cinnamon until smooth. Set aside.
6. Melt 1/2 cup brown sugar, 4 tablespoons unsalted butter, and a pinch of fine sea salt over medium heat. Whisk vigorously until fully emulsified. Remove from heat and set aside.
7. Line a 9×13 inch metal baking pan with parchment paper.
8. Spoon 1/2 tablespoon brown sugar caramel into four rows of three spots on the pan’s bottom. Top each with a pineapple ring and place a maraschino cherry in the center of each pineapple.
9. On a lightly floured surface, roll the rested dough into a 15×21-inch rectangle, with the longest side nearest you. Spread the cinnamon sugar filling evenly over the dough, leaving a 1/2-inch border at the top edge.
10. Using a pizza cutter, cut twelve 1 3/4-inch strips. Roll each strip away from you tightly and place each roll seam side down on top of each pineapple ring in the pan.
11. Cover the pan with plastic wrap and let the rolls rise for 2 hours or until doubled in size. Meanwhile, preheat the oven to 325°F (162°C).
12. Bake the rolls for 40 minutes, until the internal temperature reaches 185°F and the tops are golden brown.
13. Let the rolls cool in the pan for 20 minutes while you prepare the glaze.
14. Whisk together 1 cup powdered sugar, 2-3 tablespoons whole milk, and 1/2 teaspoon vanilla extract until smooth.
15. Place a parchment-lined baking sheet on top of the baking pan, flip the pan upside down carefully onto the sheet, remove the pan, and drizzle the rolls with the vanilla glaze. Serve warm and enjoy!

Notes

• Measure your dry ingredients properly using the spoon-level method or a kitchen scale for best results; avoid scooping flour directly.
• Store leftover rolls in an airtight container in the fridge up to 4 days. To keep moist, place a wet paper towel inside the container, not touching the rolls.
• Reheat leftovers in a 350°F oven or microwave in 20-second increments to avoid drying out.
• Ensure pineapple rings are well drained and patted dry to prevent excess moisture in the caramel base.
• Use room temperature ingredients for optimal dough texture and rise.