Pineapple Upside Down Cinnamon Rolls

A tasty creative nontraditional cinnamon roll!

Pineapple Upside Down Cinnamon Rolls


12 rolls



Prep Time


Bake Time

25 to 35 minutes

Rise Time

30 to 40 minutes

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  • 2-1/2 to 3 cups bread flour
  • 1 (2-1/4 tsp.) envelope Fleischmann’s® RapidRise® Instant Yeast
  • 3 tablespoons sugar
  • 1/2 teaspoon salt
  • 1 cup very warm milk (120º to 130ºF)
  • 1/4 cup butter OR margarine, softened
  • 1 egg
  • Topping
  • 1/2 cup butter OR margarine
  • 1 cup brown sugar
  • 2 tablespoons corn syrup, light
  • 1 can (20 ounces) crushed pineapple, drained
  • Filling
  • 1/4 cup butter OR margarine, softened
  • 1/2 cup brown sugar
  • 1 teaspoon ground cinnamon


  1. Combine 1-1/2 cups flour, undissolved yeast, sugar and salt in a large mixer bowl. Add milk, butter and egg. Beat for 2 minutes on medium speed. Add enough remaining flour to form a soft dough.
  2. Knead on a lightly floured surface for 6 to 8 minutes, until dough is smooth and elastic. Cover and let rest 10 minutes.
  3. While dough is resting, melt 1/2 cup butter in saucepan. Add brown sugar and corn syrup and bring to a boil. Add pineapple and boil for 5 minutes. Pour into a greased 13 x 9-inch baking pan. Sauce will be thin.
  4. Roll dough into a 15 x 10-inch rectangle. Spread 1/4 cup butter evenly over dough. Mix together brown sugar and cinnamon and sprinkle evenly over butter.
  5. Roll dough up tightly, starting with a long end. Pinch seam to seal. Cut dough into 12 equal sized rolls. Place rolls, cut side down, on pineapple topping in prepared pan. Cover and let rise until doubled in size, about 30 to 40 minutes.
  6. Bake for 25 to 35 minutes in a preheated 375°F oven. Cover with foil to prevent too much browning, if necessary. Cool for 2 minutes and turn out onto tray.

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