Pineapple Upside Down Cinnamon Rolls

why make this recipe

Pineapple Upside Down Cinnamon Rolls are a delightful twist on the classic cinnamon roll. They combine the sweet, buttery flavor of cinnamon rolls with the tropical taste of pineapple and the charm of an upside-down cake. This recipe will bring a touch of fun to your breakfast or brunch table. The soft, fluffy dough is filled with a rich cinnamon mixture and topped with caramelized pineapple rings and cherries, creating a beautiful and delicious dish that everyone will love.

how to make Pineapple Upside Down Cinnamon Rolls

Ingredients:

  • 2/3 cup water
  • 1/4 cup bread flour
  • 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)
  • 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 with paper towels to absorb excess moisture)
  • 12 maraschino cherries
  • 1 cup powdered sugar
  • 2-3 tablespoons whole milk
  • 1/2 teaspoon vanilla

Directions:

  1. In a small saucepan, make the tangzhong by whisking together the water and all-purpose flour. Cook over medium heat, stirring constantly, for 4-5 minutes until it becomes a paste-like slurry. Set it aside to cool.
  2. In a stand mixer bowl, combine the flour, sugar, yeast, and salt. Add the cream, milk, egg, vanilla, and tangzhong. Knead on low speed with the dough hook for around 2 minutes until it forms a rough dough ball.
  3. With the mixer running on low, add the softened butter one tablespoon at a time, letting it mix completely before adding more. Continue kneading for another 8-10 minutes until the dough is smooth and elastic.
  4. Remove the dough from the bowl and shape it into a smooth ball. Place it seam-side down in the mixing bowl, cover with plastic wrap, and let it rest for 30 minutes.
  5. While the dough rests, prepare the filling. In a bowl, mix together the brown sugar, butter, and cinnamon until smooth.
  6. To make the brown sugar caramel, melt the sugar, butter, and salt over medium heat, stirring until combined. Set this aside.
  7. Line a 9×13 metal baking pan with parchment paper. Spoon about 1/2 tablespoon of the caramel in four rows of three on the bottom of the pan. Place a pineapple ring in each spot and press a cherry into the center.
  8. Roll out the dough on a lightly floured surface into a rectangle about 15×21 inches. Spread the brown sugar filling over the dough, leaving a 1/2-inch border at the top.
  9. Use a pizza cutter to cut twelve strips, about 1 3/4 inches wide. Roll each strip away from you and place each on a pineapple ring.
  10. Cover the pan with plastic wrap and let it rise for 1-2 hours or until doubled in size. Preheat the oven to 325°F (162°C) during this time.
  11. Bake for 35-40 minutes until the internal temperature of the rolls reaches 185°F.
  12. Once baked, let the rolls cool for 20 minutes while you make the icing by whisking together the powdered sugar, milk, and vanilla until smooth.
  13. Line a large baking sheet with parchment. Flip the pan onto the sheet carefully and drizzle with icing. Enjoy them warm!

how to serve Pineapple Upside Down Cinnamon Rolls

Serve these delicious cinnamon rolls warm for the best experience. They are perfect for breakfast, brunch, or even dessert. Drizzling extra vanilla icing on top can enhance their sweetness, making them extra special. Pair them with coffee or tea for a delightful treat.

how to store Pineapple Upside Down Cinnamon Rolls

Store any leftover cinnamon rolls in an airtight container at room temperature for up to 2 days. For longer storage, place them in the fridge for up to a week. You can also freeze them. Wrap individual rolls tightly and store them in a freezer-safe bag for up to 2 months. Just reheat before serving for the best taste!

tips to make Pineapple Upside Down Cinnamon Rolls

  • Make sure all your dairy ingredients are at room temperature for better mixing.
  • When making the caramel, whisk thoroughly to ensure it is smooth and not grainy.
  • If you prefer a more intense pineapple flavor, you can add crushed pineapple to the filling.
  • Adjust the amount of cinnamon based on your taste preference.

variation (if any)

You can customize these cinnamon rolls in many ways. For a tropical twist, consider adding shredded coconut to the filling. You can also swap the pineapple for peaches or cherries if you want to try different fruity flavors.

FAQs

  1. Can I use fresh pineapple instead of canned? Yes, fresh pineapple works well in this recipe. Be sure to slice and properly dry the fresh pineapple to avoid excess moisture.
  2. What can I use instead of vanilla bean paste? You can substitute vanilla extract for the vanilla bean paste; however, the flavor may not be as rich.
  3. Can I make the dough ahead of time? Yes, you can make the dough the night before. After kneading, cover it and refrigerate it overnight. Allow it to come to room temperature before shaping and rising.

Pineapple Upside Down Cinnamon Rolls

A delightful twist on traditional cinnamon rolls featuring caramelized pineapple and cherries, perfect for breakfast or brunch.
Prep Time 45 minutes
Cook Time 40 minutes
Total Time 1 hour 25 minutes
Servings: 12 servings
Course: Breakfast, Dessert
Cuisine: American
Calories: 320

Ingredients
  

Dough Ingredients
  • 2/3 cup water
  • 1/4 cup bread flour
  • 3 2/3 cups bread flour See notes 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 Tangzhong from above
  • 6 tablespoons unsalted butter (room temperature)
Filling Ingredients
  • 2/3 cup brown sugar (packed)
  • 1/2 cup unsalted butter (room temperature)
  • 2 tablespoons ground cinnamon
Caramel Ingredients
  • 1/2 cup brown sugar (packed)
  • 4 tablespoons unsalted butter
  • Pinch fine sea salt
Topping Ingredients
  • 12 pineapple rings (drained and patted dry) Absorb excess moisture
  • 12 maraschino cherries
Icing Ingredients
  • 1 cup powdered sugar
  • 2-3 tablespoons whole milk
  • 1/2 teaspoon vanilla

Method
 

Making the Tangzhong
  1. In a small saucepan, whisk together the water and all-purpose flour to make the tangzhong, cooking over medium heat for 4-5 minutes until it becomes a paste-like slurry. Set aside to cool.
Preparing the Dough
  1. In a stand mixer bowl, combine the flour, sugar, yeast, and salt. Add the cream, milk, egg, vanilla, and tangzhong. Knead on low speed with the dough hook for around 2 minutes until it forms a rough dough ball.
  2. With the mixer running on low, add the softened butter one tablespoon at a time, letting it mix completely before adding more. Continue kneading for another 8-10 minutes until the dough is smooth and elastic.
  3. Remove the dough from the bowl and shape it into a smooth ball. Place it seam-side down in the mixing bowl, cover with plastic wrap, and let it rest for 30 minutes.
Preparing the Filling
  1. While the dough rests, mix together the brown sugar, butter, and cinnamon in a bowl until smooth.
Making the Caramel
  1. Melt the sugar, butter, and salt over medium heat, stirring until combined. Set aside.
Assembling the Rolls
  1. Line a 9×13 metal baking pan with parchment paper. Spoon about 1/2 tablespoon of the caramel in four rows of three on the bottom of the pan. Place a pineapple ring in each spot and press a cherry into the center.
  2. Roll out the dough on a lightly floured surface into a rectangle about 15×21 inches. Spread the brown sugar filling over the dough, leaving a 1/2-inch border at the top.
  3. Use a pizza cutter to cut twelve strips, about 1 3/4 inches wide. Roll each strip away from you and place each on a pineapple ring.
  4. Cover the pan with plastic wrap and let it rise for 1-2 hours or until doubled in size. Preheat the oven to 325°F (162°C) during this time.
Baking the Rolls
  1. Bake for 35-40 minutes until the internal temperature of the rolls reaches 185°F.
  2. Once baked, let the rolls cool for 20 minutes while you make the icing by whisking together the powdered sugar, milk, and vanilla until smooth.
Serving
  1. Line a large baking sheet with parchment. Flip the pan onto the sheet carefully and drizzle with icing. Enjoy warm!

Nutrition

Serving: 1gCalories: 320kcalCarbohydrates: 45gProtein: 4gFat: 15gSaturated Fat: 8gSodium: 250mgFiber: 1gSugar: 20g

Notes

For the best experience, serve rolls warm. They can be paired with coffee or tea. Store leftovers in an airtight container for up to 2 days at room temperature or refrigerate for up to a week. Freeze individual rolls for up to 2 months, reheating before serving.

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