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Pineapple Upside-Down Rolls

Author: Gwen Adams

Pineapple Upside-Down Rolls Recipe

A creative invention from the Iowa State Fair by Lana Ross of Indianola: tender, cinnamon-filled dough is baked atop sweet, coconut-laced pineapple, then flipped upside down for a show-stopping result.

At a glance

16 rolls
Nutrition information


Choose your measure:



  • 1/2 cup large-flake unsweetened coconut
  • 20 ounces drained crushed pineapple; divided, juice reserved
  • 1/4 cup unsalted butter
  • 1/2 cup brown sugar
  • 2 tablespoons light corn syrup
  • 1/4 teaspoon salt


  • 1/2 cup brown sugar, light or dark
  • 2 teaspoons cinnamon
  • 1 teaspoon Instant ClearJel or 1 tablespoon King Arthur Unbleached All-Purpose Flour
  • 1/4 teaspoon salt
  • 2 tablespoons unsalted butter, softened
  • 2 teaspoons lime juice
  • 1/4 cup drained crushed pineapple (from above)
  • 1/4 cup shredded unsweetened coconut


  1. For the dough: Pour the water into a large mixing bowl and sprinkle the yeast into it. Add the remaining ingredients, reserving 1/4 cup of flour to use only if needed. Mix the dough until it comes together; cover and let rest for 15 minutes.
  2. After the first rest, turn the dough out onto a lightly floured surface and knead until smooth and supple. Place in a greased bowl, cover, and let rise until doubled, about 1 hour.
  3. To make the topping: Butter two 8" round pans or a 9" x 13" pan. Sprinkle the large-flake coconut evenly over the bottom of the pan(s).
  4. Measure 1/4 cup of drained crushed pineapple and set it aside for the filling; sprinkle the rest over the coconut in the baking pan(s).
  5. Cook the pineapple juice in a small saucepan over medium heat until reduced to a syrupy consistency. Add the butter, brown sugar, corn syrup, and salt and cook, stirring, until the brown sugar dissolves. Pour the syrup evenly over the pineapple and coconut in the pan.
  6. To make the filling: In a medium bowl combine the brown sugar, cinnamon, ClearJel, and salt. Mix in the butter until a paste forms, then stir in the lime juice, 1/4 cup reserved pineapple, and coconut.
  7. When the dough is fully risen, deflate it and roll it out on a lightly greased work surface to a 12" x 18" rectangle. Spread the filling over the dough, leaving a 1" strip along the long edge uncovered. Roll up the dough the long way, and pinch the seam closed.
  8. Cut the dough into 1" slices and place in the pan(s). Cover and let rise for 45 to 60 minutes, until very puffy looking. Towards the end of the rising time, preheat the oven to 350°F.
  9. Bake the rolls for 20 to 25 minutes. Remove them from the oven and let them cool for 15 minutes before turning them upside down onto a serving dish to finish cooling.
  10. Enjoy warm or at room temperature. Store any leftover rolls, wrapped in plastic, at room temperature for a couple of days; freeze for longer storage.

Nutrition Information

  • Serving Size 1 roll, 82g
  • Servings Per Batch 16 rolls
Amount Per Serving:
  • Calories 192
  • Calories from Fat 99
  • Total Fat 11g
  • Saturated Fat 8g
  • Trans Fat 0g
  • Cholesterol 43mg
  • Sodium 242mg
  • Total Carbohydrate 22g
  • Dietary Fiber 1g
  • Sugars 20g
  • Protein 2g

* The nutrition information provided for this recipe is determined by the ESHA Genesis R&D software program. Substituting any ingredients may change the posted nutrition information.