Pineapple Upside-Down Cinnamon Rolls: A Tropical Twist on a Beloved Classic
Sometimes, the best ideas come from unexpected places. I was challenged by a reader with a concept so brilliant, I wondered why I hadn’t thought of it myself: Pineapple Upside-Down Cinnamon Rolls. My initial thought was, “Could that even truly work?” And the answer, a resounding yes, exceeded all expectations! Much like my incredibly popular tropical Pina Colada Rolls, this innovative recipe surprised and delighted me in the most delicious way.
Imagine the delightful combination of a classic pineapple upside-down cake and your favorite bakery-style cinnamon roll. This recipe delivers just that: the same wonderfully soft, sticky, and perfectly caramelized pineapple, complete with bright red maraschino cherries, baked right into the bottom of my signature fluffy cinnamon roll dough. The magic truly happens when these golden-brown beauties are flipped, revealing a stunning, glossy, fruit-laden topping that’s utterly irresistible. It’s an experience that’s even more fantastic than it sounds, offering a unique blend of fruity sweetness, warm spice, and tender dough that will transport your taste buds straight to paradise.
This summer, my culinary explorations have been heavily influenced by nostalgic childhood desserts, leading to an exciting series of innovative cinnamon roll creations. Among them, Chocolate S’mores Cinnamon Rolls quickly became a fan favorite! Loaded with rich chocolate, perfectly toasted marshmallows, and buttery graham cracker crumbs, they’re a truly delightful treat that captures the essence of summer campfires in every bite. This quest for reinventing beloved classics is what ultimately paved the way for these incredible pineapple upside-down rolls, blending the comforting familiarity of cinnamon rolls with an exciting tropical twist.
Mastering the Baking Process for Perfect Pineapple Upside-Down Cinnamon Rolls
Creating these sensational Pineapple Upside-Down Cinnamon Rolls involves a few key steps that ensure maximum flavor and an incredibly tender texture. From preparing the unique tangzhong roux to assembling the vibrant pineapple topping, each stage contributes to the final masterpiece. Follow this detailed guide to achieve bakery-quality results right in your own kitchen.
1
Begin with the Tangzhong. This essential technique, often utilized in various breads and pastries, is a game-changer for achieving an incredibly soft, moist, and fluffy dough. It’s a simple flour and water roux that locks in moisture, ensuring your cinnamon rolls stay fresh longer. To prepare it, simply whisk flour and water together in a small saucepan and cook over medium heat until it transforms into a thick, pudding-like paste. Allow it to cool slightly before incorporating it into your dough mixture.
2
Combine Wet and Dry Ingredients. In the bowl of your stand mixer, add all the dry ingredients (flour, sugar, yeast, salt) and give them a quick whisk. Then, pour in the wet ingredients (heavy cream, milk, egg, vanilla, and your prepared tangzhong). Mix on low speed using the dough hook attachment. The dough will initially look shaggy and a bit rough, which is perfectly normal. Don’t be alarmed; this is just the beginning of its transformation.
3
Knead in the Butter and Develop the Dough. With the mixer still running on low, gradually add the softened unsalted butter, one tablespoon at a time. It’s important to let each piece fully incorporate before adding the next. Once all the butter is in, continue kneading for another 8-10 minutes. This extended kneading time is crucial for developing the gluten, resulting in a smooth, elastic, and remarkably soft dough. When properly kneaded, the dough should pull away cleanly from the sides of the bowl and feel soft and tacky, but not sticky to the touch. This elasticity is what gives the cinnamon rolls their signature fluffy texture.
4
Allow the Dough to Rest. Once the dough is beautifully kneaded, remove it from the mixer bowl. Gently pull the edges into the center to form a smooth, round ball. Place it seam-side down back into the bowl, cover it tightly with plastic wrap, and let it rest at room temperature for 30 minutes. This resting period is not for rising, but rather for allowing the gluten to relax, making the dough much easier to roll out evenly in the subsequent step. While the dough is resting, you can prepare your delectable cinnamon sugar filling.
5
Prepare the Caramel and Fruit Base. This is where the “upside-down” magic truly begins. First, create your luscious brown sugar caramel by melting brown sugar, butter, and a pinch of fine sea salt over medium heat. Whisk vigorously until the butter and sugar are beautifully emulsified, forming a smooth, golden syrup. Next, line a 9×13 metal baking pan with parchment paper – a metal pan with sharp corners is vital here, as it ensures all 12 pineapple slices fit perfectly without being squeezed. Spoon about 1/2 tablespoon of the warm caramel into twelve spots on the pan, arranged in four rows of three. Gently place a drained and patted dry pineapple ring over each caramel spot, then nestle a vibrant maraschino cherry into the center of each pineapple ring. This creates the stunning, sticky bottom layer that will become the top of your rolls.
6
Roll Out the Dough and Fill. Transfer your rested dough to a lightly floured surface. Using a rolling pin, carefully roll the dough into a large 15×21-inch rectangle, ensuring the longest side is closest to you. Spread your prepared cinnamon sugar filling evenly across the entire surface of the dough, leaving a small 1/2-inch clean border at the top edge. This ensures the filling doesn’t seep out when you roll. Then, using a pizza cutter or a very sharp knife, cut the dough into twelve even 1 3/4-inch strips. Starting from the bottom (the side closest to you), roll each strip tightly away from you to form perfectly swirled cinnamon rolls. The tighter the roll, the better they will hold their shape.
My journey through summer-inspired cinnamon rolls continued to bring forth exciting creations! After these pineapple rolls, I was inspired to make an Orange Creamsicle Roll. This roll is wonderfully soft and bursting with bright citrus flavor, all finished with a creamy vanilla glaze. It perfectly evokes the nostalgic taste of those classic popsicles from childhood summers. If you’re a fan of vibrant, fruity twists on traditional bakes, these are definitely worth exploring.
7
Arrange Rolls on Pineapple Base. Carefully place each rolled cinnamon roll on top of a pineapple slice in your prepared baking pan. Gently press the top of each roll against the pineapple to ensure good contact and secure it in place. This intimate contact is essential for the caramel and fruit to adhere beautifully to the rolls during baking and when you flip them. Make sure they are snuggled in, but not overly crowded, to allow for proper rising.
8
Proof the Rolls to Perfection. Cover the pan loosely with plastic wrap or a clean kitchen towel and allow the cinnamon rolls to rise in a warm, draft-free place for 1-2 hours, or until they have visibly doubled in size. This proofing stage is vital for a light and airy texture. When they are ready to bake, they should look noticeably larger, feel soft and pillowy to the touch, and gently spring back when lightly poked. While they are rising, preheat your oven to 325°F/162°C to ensure it’s at the correct temperature when the rolls are ready.
9
Bake to Golden Perfection. Place the pan in the preheated oven and bake for approximately 35-40 minutes. You’re looking for a beautiful light golden-brown color on top of the rolls. For the most accurate measure of doneness and to ensure that famously gooey center, use an instant-read thermometer to check the internal temperature of the center roll; it should reach 185°F (85°C). This temperature indicates that the dough is fully cooked but still wonderfully soft and moist, preventing any dryness.
10
Cool, Flip, and Glaze. Once baked, remove the pan from the oven and let the rolls cool for about 20 minutes in the pan. This allows the caramel to set slightly and helps prevent the rolls from sticking when flipped. While they are cooling, prepare a simple yet delicious vanilla glaze by whisking powdered sugar, whole milk, and vanilla extract until smooth. After 20 minutes, place a parchment-lined baking sheet firmly over the baking pan. With a swift and confident motion, carefully flip the entire pan upside down onto the baking sheet. Gently lift the baking pan away, revealing the stunning caramelized pineapple and cherry topping. Drizzle generously with your vanilla glaze and serve warm for the ultimate indulgence!
Tips for Success: Ensuring Perfect Pineapple Upside-Down Cinnamon Rolls Every Time
- Measure Precisely, Especially Flour: My #1 baking tip! Never scoop flour directly with your measuring cup, as this compacts it and leads to using too much. Instead, fluff the flour in its container, then spoon it lightly into your measuring cup and level off the top. For the absolute best and most consistent results, always use a kitchen scale to measure your dry ingredients by weight.
- Room Temperature Ingredients: Ensure your heavy cream, milk, egg, and butter are all at room temperature. This allows them to incorporate smoothly into the dough, creating a more cohesive and evenly textured final product.
- Don’t Rush the Kneading: The kneading process, especially after adding butter, is crucial for developing gluten. A well-kneaded dough will be smooth, elastic, and will yield a wonderfully soft and chewy cinnamon roll.
- Proper Proofing Environment: Find a warm, draft-free spot for your dough to rise. If your kitchen is cool, you can lightly warm your oven to its lowest setting (then turn it off!), or place the covered dough in a warm corner.
- Metal Pan is Key: As mentioned in the recipe, a metal 9×13 inch baking pan with sharp, rather than rounded, corners is ideal. This ensures that all 12 pineapple rings fit snugly, creating a uniform and beautiful presentation.
- Don’t Skip Draining the Pineapple: Excess moisture from the pineapple can make the caramel too watery. Patting the pineapple rings dry thoroughly with paper towels before placing them in the pan is a small but important step.
- The Flip: The flip can be a moment of truth! Be confident and quick. Placing a parchment-lined baking sheet directly over the pan and flipping decisively will give you the best reveal.
The exploration of delightful, nostalgic desserts infused into cinnamon rolls is a passion of mine. Beyond the tropical paradise of these pineapple rolls, and the comforting flavors of s’mores, another summer classic found its way into my baking repertoire: Gooey Peach Cobbler Rolls! Just like the beloved original dessert, these rolls are generously layered with sweet, jammy peaches and crowned with a golden, buttery cinnamon crumble. And for those who can’t get enough citrus, my Key Lime Pie Rolls offer a zesty, tangy experience that rivals even the classic pie itself. Each creation is a testament to the versatility and comforting appeal of the humble cinnamon roll, transformed into something extraordinary.
Storage and Reheating Tips
To enjoy these Pineapple Upside-Down Cinnamon Rolls at their best, it’s always recommended to serve them warm, fresh from the oven. However, if you find yourself with leftovers, they can be stored in an airtight container in the refrigerator for up to 4 days. To maintain their delightful moisture and prevent them from becoming stale, a clever trick is to place a slightly damp paper towel in the container, ensuring it doesn’t directly touch the rolls. When you’re ready to indulge again, simply reheat them in a preheated 350°F (175°C) oven for about 10-15 minutes, or in the microwave in 20-second increments until warmed through. This will help bring back their soft texture and gooey caramel topping, making them almost as good as freshly baked.
If you tried this recipe or any other delightful creation on my website, I would absolutely love to hear from you! Please share your experience and how it went in the comments section below. Your feedback is invaluable, and I truly enjoy connecting with fellow bakers and food enthusiasts. While you’re there, don’t forget to leave a star rating to help other readers discover this fantastic recipe! You can also share your beautiful creations by tagging me on Instagram or Facebook – I can’t wait to see your Pineapple Upside-Down Cinnamon Rolls!
Pineapple Upside Down Cinnamon Rolls
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Equipment
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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
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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
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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
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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
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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.
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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
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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
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Line a metal 9×13 baking pan with parchment paper.
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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
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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.
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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.
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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.
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Bake for 35-40 minutes or until the internal temperature of the center rolls reaches 185°F.
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Once baked, let the rolls cool for 20 minutes while you make the icing.
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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
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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
Storage: Leftover rolls can be stored in an airtight container in the fridge for up to 4 days. They can be reheated in a 350°F oven or in the microwave in 20-second increments. *To prevent the rolls from becoming stale, leave a wet paper towel in the container, not touching the rolls, to maintain moisture.*
The calorie information provided for the recipe is an estimate. The accuracy of the calories listed is not guaranteed.