Sticky and Sweet Pineapple Upside-Down Cinnamon Rolls
A brilliant, simple fusion dessert! Your favorite cinnamon rolls baked directly on top of a buttery brown sugar glaze, pineapple rings, and cherries for a stunning upside-down pastry.
Equipment
- 9x13-inch baking dish (or individual square molds)
- Large baking sheet or cutting board (for flipping)
Ingredients
- 1 batch go-to cinnamon roll dough homemade or 2 tubes jumbo canned rolls
- 1/2 cup 1 stick unsalted butter, melted
- 1 cup light or dark brown sugar packed
- 1 20 oz can pineapple slices in juice (drained well)
- 10 maraschino cherries stems removed, drained well
Instructions
- Preheat your oven to the temperature specified by your cinnamon roll recipe (usually 350°F to 375°F). Lightly spray a 9x13-inch baking dish with non-stick spray.
- Pour the melted butter evenly over the bottom of the baking dish.
- Sprinkle the packed brown sugar in a thick, even layer over the melted butter.
- Pat the drained pineapple rings and cherries completely dry with a paper towel.
- Arrange the pineapple rings in a single layer over the brown sugar. Place one cherry into the center hole of each pineapple ring.
- Place one unbaked cinnamon roll directly on top of each pineapple ring.
- If using homemade dough, cover and let proof until doubled in size. If using canned dough, proceed immediately to baking.
- Bake according to your dough's recipe instructions (usually 25-30 minutes), until the dough is golden brown and cooked through.
- Remove the pan from the oven and let it sit undisturbed for exactly 5 minutes.
- Place a large cutting board or platter over the top of the baking dish. Using oven mitts, quickly invert the pan. Gently remove the baking dish to reveal the caramelized rolls. Serve warm!
Notes
Dry the Fruit: Ensure you pat the canned fruit completely dry. Excess moisture will thin out your caramel glaze.
The Flip: Do not skip the 5-minute wait time! This allows the syrup to thicken, but keeps it hot enough that the rolls won't stick to the pan.