Print
clock clock iconcutlery cutlery iconflag flag iconfolder folder iconinstagram instagram iconpinterest pinterest iconfacebook facebook iconprint print iconsquares squares iconheart heart iconheart solid heart solid icon
Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls

Pineapple Upside Down Cinnamon Rolls are a tropical delight that takes the classic cinnamon roll to new heights. Soft, fluffy dough is swirled with cinnamon and brown sugar, then topped with caramelized pineapple rings and cherries for a sweet, sticky finish. Perfect for summer brunches or family gatherings, these rolls offer a refreshing twist on a beloved favorite. With an easy-to-follow recipe and simple ingredients, you can create a showstopper that everyone will love.

  • Total Time: 1 hour 20 minutes
  • Yield: 12 servings 1x

Ingredients

Scale
  • 3/4 cup water
  • 4 cups bread flour
  • 1/3 cup granulated sugar
  • 2 teaspoons instant yeast
  • 1 teaspoon sea salt
  • 1/3 cup heavy cream
  • 1/3 cup whole milk
  • 1 large egg
  • 12 pineapple rings
  • 12 maraschino cherries
  • Brown sugar, unsalted butter, cinnamon, powdered sugar for icing

Instructions

  1. Make the Tangzhong: Whisk water and bread flour in a saucepan over medium heat until thickened. Let cool.
  2. Prepare the Dough: In a stand mixer, combine flour, sugar, yeast, salt. Add cream, milk, egg, vanilla, and tangzhong. Knead until smooth.
  3. Incorporate Butter: Gradually add softened butter while kneading until fully combined and elastic.
  4. Let Rise: Shape into a ball and let it rise covered until doubled in size (about 30 minutes).
  5. Make Filling: Mix brown sugar, butter, and cinnamon in a bowl.
  6. Prepare Caramel: Melt brown sugar and butter in a saucepan; set aside to cool slightly.
  7. Assemble: Line baking pan with parchment paper; layer caramel, pineapple rings, and cherries at the bottom before placing rolled dough.
  8. Final Rise: Cover the assembled rolls and let them rise again until doubled.
  9. Bake: Preheat oven to 325°F; bake for about 35–40 minutes until golden.
  10. Cool & Ice: Cool slightly before flipping onto serving dish and drizzling with icing made from powdered sugar and milk.
  • Author: Natalia
  • Prep Time: 40 minutes
  • Cook Time: 40 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: Tropical

Nutrition

  • Serving Size: 1 roll (90g)
  • Calories: 290
  • Sugar: 18g
  • Sodium: 170mg
  • Fat: 10g
  • Saturated Fat: 6g
  • Unsaturated Fat: 4g
  • Trans Fat: 0g
  • Carbohydrates: 46g
  • Fiber: 2g
  • Protein: 5g
  • Cholesterol: 30mg

Keywords: Use room temperature ingredients for optimal mixing. Allow sufficient rising time for fluffy rolls. Customize with nuts or coconut flakes if desired.