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A close up of a freshly baked, glossy pineapple upside down cinnamon roll featuring a caramelized pineapple ring and a bright red cherry in the center, sitting in a white bakery box.

Pineapple Upside Down Cinnamon Rolls

A sticky, sweet mashup of classic pineapple upside-down cake and gooey cinnamon rolls. An easy and impressive breakfast treat!
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Ingredients Equipment Method Notes

Ingredients
  

  • 1 batch cinnamon roll dough homemade, or 2 cans jumbo store-bought
  • ½ cup unsalted butter melted
  • 1 cup light brown sugar packed
  • 1 can 20 oz pineapple slices (drained)
  • 12 maraschino cherries stems removed
  • 1 tsp ground cinnamon optional

Equipment

  • 9x13 inch baking dish
  • Mixing bowls
  • Wire cooling rack
  • Large serving tray or cutting board (for flipping)

Method
 

  1. Prep the pan: Preheat your oven to 375°F (or according to your dough package directions). Pour the melted butter evenly into the bottom of a 9x13 inch baking dish.
  2. Add the sugar: Sprinkle the packed brown sugar evenly over the melted butter. Dust with a little cinnamon if desired.
  3. Layer the fruit: Arrange the drained pineapple slices in a single layer over the sugar. Place one maraschino cherry in the center of each pineapple ring.
  4. Add the dough: Place the unbaked cinnamon roll dough slices directly on top of the fruit. (If using homemade yeast dough, let rise until doubled).
  5. Bake: Bake for 20-25 minutes, or until the dough is golden brown and baked through, and the caramel is bubbling.
  6. Rest: Remove from the oven and let the pan sit on a wire rack for EXACTLY 5 minutes.
  7. Invert: Place a large serving tray over the baking dish and carefully flip it over. Lift the baking dish away to reveal the glazed rolls. Serve warm.

Notes

Drying the fruit: Pat your pineapple and cherries dry with a paper towel before using to prevent a watery glaze.
The Flip: Do not wait longer than 5 minutes to flip the pan, or the caramel will harden and stick to the bottom.