Leave it to a reader to challenge me with an idea I didn’t know I needed: pineapple upside down cinnamon rolls. At first, I was like… could that even work? (Spoiler: it totally does.) Just like my tropical pina colada rolls, this one surprised me in the best way.
You get the same soft, sticky, caramelized pineapple of the classic cake baked right into the bottom of my favorite bakery-style cinnamon roll, that gets flipped for that perfect upside-down reveal. Yes, it’s even better than it sounds!
My summer-inspired cinnamon roll series had me thinking about every dessert I loved as a kid, so of course, chocolate s’mores cinnamon rolls made the list! They’re loaded with chocolate, toasted marshmallows, and buttery graham crumbs… so yum!
The Baking Process
1
Make the tangzhong. I learned this technique in pastry school, which is used in many breads and pastries to achieve a super-soft and moist texture. Stir and cook the flour and water roux until it thickens into a soft, pudding-like paste.
2
Combine the wet and dry ingredients in a stand mixer bowl. Add all the ingredients to the mixer bowl and mix until the dough comes together into a shaggy mass. It’ll look a little rough at first, and that’s totally normal.
3
Knead in the butter, then knead until a smooth, elastic dough ball forms. Keep mixing until the dough turns smooth and stretchy. It should pull away from the sides of the bowl and feel soft and tacky, not sticky.
4
Let the dough rest for 30 minutes. This time is crucial for allowing the gluten to relax, making it easier to roll out in the next step.
5
Layer the brown sugar caramel, pineapple slices, and maraschino cherries on the bottom of a 9×13 baking pan. Using a metal pan is key to fitting the pineapple slices. When testing this recipe, I found that pans with rounded edges can’t fit all 12!
6
Roll out the dough and spread the cinnamon sugar filling evenly across it. Then, cut the dough into strips and roll each one up. Use a pizza cutter or a sharp knife to cut the dough!
After creating this recipe, I kept thinking about other summery desserts I grew up with, so I made an orange creamsicle roll, too! It’s soft and citrusy with a vanilla glaze that reminds me of those popsicles from every childhood summer.
7
Place the rolls on top of the pineapple slices. Gently press the top of the roll against the pineapple to secure it in place.
8
Let the cinnamon rolls rise until they double in size. When ready to bake, they should feel soft and slightly pillowy.
9
Bake the rolls! You’re aiming for a light golden brown top and an internal temperature of 185°F for the center roll to achieve a gooey texture.
10
Let cool for 20 minutes, then flip upside down onto a parchment-lined baking sheet. Drizzle the tops with vanilla glaze and enjoy warm!
Next up in the cinnamon roll lineup is gooey peach cobbler rolls! Like the classic, they’re layered with sweet, jammy peaches and topped with a golden cinnamon crumble. Or maybe you’re craving more citrus…then my key lime pie rolls are perfect. They taste even better than the original!
If you tried this or any other recipe on my website, please let me know how it went in the comments; I love hearing from you! Also, please leave a star rating while you’re there! You can also tag me on Instagram or Facebook so I can check it out!
Pineapple Upside Down Cinnamon Rolls
Equipment
- metal 9×13 pan
Ingredients
For the Tangzhong
- 3/4 cup water
- 1/4 cup bread flour
For the Cinnamon Roll Dough
- 3 2/3 cups bread flour, *See notes below for measuring*
- 1/3 cup granulated sugar
- 2 teaspoons instant yeast
- 1 teaspoon fine sea salt
- 1/3 cup heavy cream, room temperature
- 1/3 cup whole milk, room temperature
- 1 large egg, room temperature
- 1 teaspoon vanilla bean paste
- Tangzhong from above
- 6 tablespoons unsalted butter, room temperature
For the Cinnamon Sugar Filling
- 2/3 cup brown sugar, packed
- 1/2 cup unsalted butter, room temperature
- 2 tablespoons ground cinnamon
For the Brown Sugar Caramel Base
- 1/2 cup brown sugar, packed
- 4 tablespoons unsalted butter
- Pinch fine sea salt
- 12 pineapple rings, drained and patted dry with paper towels to absorb excess moisture
- 12 maraschino cherries
For the Vanilla Glaze
- 1 cup powdered sugar
- 2-3 tablespoons whole milk
- 1/2 teaspoon vanilla
Instructions
- In a small saucepan, make the tangzhong by whisking together the water and all-purpose flour. Cook over medium heat, whisking constantly, for 4-5 minutes until the mixture is a paste-like slurry. Scrape it into a bowl and set it aside until ready to use.3/4 cup (155 g) water, 1/4 cup (32 g) bread flour
- In a stand mixer bowl, mix the flour, sugar, yeast, and salt. Add the cream, milk, egg, vanilla, and tangzhong to the bowl. Knead on low speed with the dough hook for 2 minutes until it forms a rough dough ball.3 2/3 cups (485 g) bread flour, 1/3 cup (66 g) granulated sugar, 2 teaspoons (6 g) instant yeast, 1 teaspoon (4 g) fine sea salt, 1/3 cup (78 g) heavy cream, 1/3 cup (78 g) whole milk, 1 (50 g) large egg, 1 teaspoon (4 g) vanilla bean paste, Tangzhong from above
- With the mixer running on low, add the softened butter one tablespoon at a time, letting it fully incorporate before adding more. Then, continue kneading for another 8-10 minutes or until the dough looks smooth and elastic.6 tablespoons (84 g) unsalted butter
- Remove the dough from the bowl and pull the sides into the bottom to create a smooth round ball. Place it seam-side down back into the mixing bowl. Cover with plastic wrap and set aside to rest for 30 minutes.
- While the dough rests, make the filling. In a medium bowl with a spoon or in a mixer bowl, combine the brown sugar, butter, and cinnamon until smooth. Set aside.2/3 cup (133 g) brown sugar, 1/2 cup (109 g) unsalted butter, 2 tablespoons (12 g) ground cinnamon
- Make the brown sugar caramel. Melt the sugar, butter, and salt over medium heat until the butter is melted. Whisk vigorously until the butter is emulsified with the sugar. Set it aside while you prepare the pan.1/2 cup (100 g) brown sugar, 4 tablespoons (56 g) unsalted butter, Pinch fine sea salt
- Line a metal 9×13 baking pan with parchment paper.
- Spoon roughly 1/2 tablespoon of the brown sugar caramel on the bottom of the pan in four rows of three. Place a pineapple ring into the caramel in each spot, then press a cherry into the center.12 pineapple rings, 12 maraschino cherries
- Place the rested dough on a lightly floured surface. Roll it out into a 15×21-inch rectangle, with the longest side closest to you. Spread the brown sugar filling across the surface of the dough, leaving a 1/2-inch border clean at the top.
- Use a pizza cutter to cut twelve 1 3/4-inch strips. Roll each strip away from you, then place each on a pineapple ring.
- Cover the pan with plastic wrap and set it aside to rise for 1-2 hours or until the rolls double in size. Meanwhile, preheat the oven to 325°F/162°C.
- Bake for 35-40 minutes or until the internal temperature of the center rolls reaches 185°F.
- Once baked, let the rolls cool for 20 minutes while you make the icing.
- Whisk together the powdered sugar, milk, and vanilla until smooth.1 cup (120 g) powdered sugar, 1/2 teaspoon vanilla, 2-3 tablespoons (24 g) whole milk
- Line a large baking sheet with parchment paper and set it on top of the baking pan. Carefully flip the pan upside down onto the baking sheet and remove the pan. Drizzle with vanilla icing and enjoy warm!
Notes
Tried this recipe?Leave a comment below & tag @cambreabakes on social!
