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Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls

Indulge in the delightful experience of Pineapple Upside Down Cinnamon Rolls, where fluffy dough meets a sumptuous topping of caramelized pineapple and cherries. This creative twist on a beloved classic is perfect for breakfast, brunch, or dessert. Each roll is bursting with tropical flavor and features an impressive presentation that will wow your guests when flipped over. With simple ingredients and clear instructions, even novice bakers can achieve this showstopper. Enjoy the gooey goodness that perfectly complements the soft cinnamon roll dough, making it a favorite for any occasion!

  • Total Time: 1 hour 25 minutes
  • Yield: Makes approximately 12 servings 1x

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
  • 1/3 cup heavy cream (room temperature)
  • 1/3 cup whole milk (room temperature)
  • 1 large egg (room temperature)
  • 12 pineapple rings (drained and patted dry)
  • 12 maraschino cherries
  • 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
  • 1 cup powdered sugar
  • 2–3 tablespoons whole milk
  • 1/2 teaspoon vanilla

Instructions

  1. Prepare Tangzhong by whisking water and bread flour in a saucepan over medium heat until paste-like.
  2. In a stand mixer, combine remaining bread flour, sugar, yeast, and salt. Add cream, milk, egg, vanilla, and Tangzhong; knead for about 10 minutes until smooth.
  3. Shape dough into a ball, let it rest for 30 minutes.
  4. Make the filling by mixing brown sugar with room-temperature butter and cinnamon.
  5. Prepare caramel by melting brown sugar with butter and sea salt in a saucepan.
  6. Assemble by layering caramel in a lined baking pan with pineapple rings and cherries.
  7. Roll out the dough, spread the filling, cut into strips, roll up, and place on top of fruit in the pan.
  8. Cover and let rise for about 1-2 hours until doubled.
  9. Bake at 325°F for 35-40 minutes until golden brown.
  • Author: Emmeline
  • Prep Time: 45 minutes
  • Cook Time: 40 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 serving
  • Calories: 260
  • Sugar: 18g
  • Sodium: 310mg
  • Fat: 8g
  • Saturated Fat: 5g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 41g
  • Fiber: 2g
  • Protein: 4g
  • Cholesterol: 30mg

Keywords: Ensure all dairy ingredients are at room temperature for optimal results. Experiment with different fruits like peaches or apples for variety. Allow sufficient rising time to achieve fluffy rolls.

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