Upside Down Apple Pie Cinnamon Rolls

There’s something magical about combining two beloved breakfast classics into one show-stopping treat. These Upside Down Apple Pie Cinnamon Rolls bring together the cozy warmth of homemade apple pie with the irresistible sweetness of cinnamon rolls. The result? A gooey, caramelized masterpiece that’s perfect for weekend mornings, holiday brunches, or whenever you’re craving serious comfort food.

What makes this recipe truly special is how the soft, pillowy cinnamon buns bake directly on top of a bubbling apple pie filling. When you flip the pan over, you reveal a gorgeous caramelized apple topping that looks like it took hours to create. But here’s the secret—this impressive dessert-meets-breakfast comes together in under 40 minutes using store-bought cinnamon rolls and simple pantry staples.

Why You’ll Love This Recipe

This recipe hits all the right notes for busy home bakers who want impressive results without spending hours in the kitchen. The convenience of canned cinnamon rolls means you skip the time-consuming dough-making process, while the homemade apple filling adds that fresh, from-scratch flavor everyone craves.

The combination of tart Granny Smith apples with brown sugar and butter creates a filling that’s not too sweet, balancing perfectly with the sugary cinnamon rolls. As everything bakes together, the apple juices mingle with the butter and sugar, forming a luscious caramel sauce that seeps into every crevice of the rolls.

Whether you’re hosting a brunch, treating your family to a special weekend breakfast, or bringing a dish to a potluck, these upside down cinnamon rolls never fail to impress. They look fancy, taste incredible, and come together faster than you’d expect.

Ingredients You’ll Need

For the Apple Pie Filling

• 2 Granny Smith apples, peeled and diced into small cubes
• ¼ cup packed brown sugar
• ¼ cup unsalted butter
• 2 teaspoons ground cinnamon

For the Cinnamon Rolls

• 1 can refrigerated cinnamon rolls (the kind with icing included)
• 1 tablespoon caramel sauce

The beauty of this ingredient list is its simplicity. Granny Smith apples are ideal because their tartness prevents the dish from becoming overly sweet, and they hold their shape well during baking. If you can’t find Granny Smiths, Honeycrisp or Braeburn apples work as alternatives.

Step-by-Step Instructions

Prepare the Apple Filling

Start by peeling your apples and cutting them into small, uniform dice—aim for pieces about ½ inch in size. This ensures they cook evenly and soften perfectly during the baking time.

In a medium saucepan, combine your diced apples with the brown sugar, butter, and cinnamon. Place the pan over medium heat and stir occasionally as the mixture warms up. You’ll notice the butter melting first, followed by the sugar dissolving and coating the apples. This process takes about 3-5 minutes.

The goal here isn’t to fully cook the apples—just to get the sugar and butter melted and mixed. The apples will finish cooking in the oven. Once everything is combined and the mixture looks glossy, remove it from the heat.

Assemble the Rolls

Pour your warm apple mixture into a 9-inch round cake pan, spreading it evenly across the bottom. This layer will become your beautiful topping after flipping.

Open your can of cinnamon rolls and separate them. Place one roll in the center of the pan, then arrange the remaining four rolls evenly around it. Don’t worry if there are small gaps between the rolls—they’ll expand as they bake and fill in the spaces.

Bake to Perfection

Preheat your oven to 350°F and slide your pan onto the middle rack. Bake for 25-30 minutes, until the cinnamon rolls are golden brown on top and cooked through. You’ll know they’re done when they spring back lightly when touched and the edges are slightly crispy.

The aroma that fills your kitchen during this time is absolutely intoxicating—cinnamon, caramelized apples, and butter all mingling together.

The Big Flip

This is the moment of truth! Let your pan cool for about 5 minutes after removing it from the oven. This brief cooling period is crucial—it allows the caramel to set just enough so it won’t run everywhere when you flip.

Place a large serving plate over the top of your cake pan. Using oven mitts, hold both the plate and pan firmly together, then quickly flip them over. Gently lift the pan away, revealing your beautiful upside down creation. If any apples stick to the pan, simply scrape them off and place them back on top.

Add the Finishing Touch

Take the icing packet that came with your cinnamon rolls and empty it into a small microwave-safe bowl. Add your tablespoon of caramel sauce to the same bowl. Microwave for about 10 seconds, just until the mixture is warm and easy to stir.

Whisk the caramel and icing together until smooth and well combined. Drizzle this sweet glaze generously over your warm cinnamon rolls, letting it cascade down the sides and pool around the apples.

Tips for Success

For the best results, make sure your apples are cut into uniform pieces. Larger chunks won’t soften properly, while pieces that are too small will turn mushy.

Don’t skip the cooling time before flipping. If you flip too soon, the hot caramel will run off. If you wait too long, the rolls might stick to the pan.

Use a good quality non-stick cake pan or lightly grease your pan before adding the apple mixture. This ensures a clean release when you flip.

Storage and Reheating

These cinnamon rolls are absolutely best served fresh and warm, right after you drizzle on that caramel glaze. However, life happens, and sometimes you need to make them ahead or save leftovers.

Store any leftover rolls in an airtight container at room temperature for up to two days. The texture will change slightly as they sit, but they’re still delicious.

For longer storage, refrigerate them for up to four days. I don’t recommend freezing this recipe—the apples and rolls don’t thaw well together, and you’ll lose that perfect texture.

To reheat individual servings, pop them in the microwave for 30 seconds. The rolls will warm through and the caramel will get gooey again.

Serving Suggestions

These upside down apple pie cinnamon rolls are substantial enough to serve as a complete breakfast or brunch item. However, they’re also wonderful as a dessert when served with a scoop of vanilla ice cream on top.

For a complete brunch spread, pair them with crispy bacon, scrambled eggs, and fresh fruit. The savory elements balance out the sweetness perfectly.

Coffee or hot apple cider make excellent beverage companions, complementing the cinnamon and apple flavors beautifully.

Variations to Try

Once you’ve mastered the basic recipe, try experimenting with different apple varieties or adding chopped pecans to the apple mixture for extra crunch. You could also substitute the caramel sauce with maple syrup for a different flavor profile.

For a more indulgent version, add a cream cheese drizzle on top along with the caramel. Simply mix softened cream cheese with powdered sugar and a splash of milk until smooth.