Upside Down Caramel Apple Cinnamon Rolls
The coziest fall brunch and quite possibly my favorite brunch to make is these Upside Down Caramel Apple Cinnamon Rolls. They combine classic, soft, fluffy cinnamon rolls with apple pie and gooey sticky buns. The cinnamon rolls sit on top of a bed of warm, bubbling homemade caramel and crisp, sweet apples. As the rolls bake, the caramel bubbles up into the cinnamon rolls. After baking the cinnamon rolls are flipped upside down to reveal a tender layer of glossy, caramel apples. My favorite part is watching the warm caramel drizzle down the rolls. Of course, a cinnamon roll is not complete without some icing, so these rolls have a drizzle of cream cheese icing for the finishing touch.

Upside Down Caramel Apple Cinnamon Rolls
- Total Time: 1 hour 55 minutes
- Yield: 7 cinnamon rolls 1x
Description
The coziest fall brunch and quite possibly my favorite brunch to make is these Upside Down Caramel Apple Cinnamon Rolls. They combine classic, soft, fluffy cinnamon rolls with apple pie and gooey sticky buns. The cinnamon rolls sit on top of a bed of warm, bubbling homemade caramel and crisp, sweet apples. As the rolls bake, the caramel bubbles up into the cinnamon rolls. After baking the cinnamon rolls are flipped upside down to reveal a tender layer of glossy, caramel apples. My favorite part is watching the warm caramel drizzle down the rolls. Of course, a cinnamon roll is not complete without some icing, so these rolls have a drizzle of cream cheese icing for the finishing touch.
Ingredients
Caramel
- 3/4 cup granulated sugar
- 4 tablespoons unsalted butter
- 1/4 cup heavy cream
Cinnamon Roll Dough
- 2 1/4 teaspoons instant yeast
- 1 cup whole milk, warmed between 106 – 112F
- 3 tablespoons granulated sugar
- 4 cups bread flour
- 1/4 cup Greek yogurt
- 2 large eggs
- 4 tablespoons unsalted butter, softened
- 1/2 teaspoon salt
Cinnamon Sugar Filling
- 8 tablespoons unsalted butter, semi-melted
- 3/4 cup brown sugar
- 1 1/2 tablespoons cinnamon
Apples
- 1–2 medium apples, thinly sliced (I used Pink Lady)
Icing
- 1 tablespoon cream cheese, softened
- 1/4 cup powdered sugar
Instructions
1. Make the dough. In the bowl of a stand mixer fitted with the dough hook attachment, add instant yeast, warm milk and granulated sugar. Allow the mixture to sit for 2-3 minutes while you measure the remaining ingredients. This is not necessary, but I like to do this step just to ensure the yeast is active and working. The mixture will have a yeast smell to it and be frothy on the surface.
Add in the bread flour, Greek yogurt, eggs, softened butter and salt. Knead the mixture on medium-low speed for 5 minutes.
Transfer the dough to a lightly greased bowl. Spray the top of the dough with nonstick spray, or drizzle with a small amount of vegetable or canola oil. This is to help the dough from sticking. Cover the dough with plastic wrap.
2. Rise time. Allow the dough to rise in a warm place for 1 hour.
3. Make the caramel. When the dough is almost done rising, make the caramel.. In a medium sized saucepan, add granulated sugar.
Cook over medium heat, stirring constantly until the sugar is melted.
Once the sugar is melted, reduce the heat to low, and add in the butter. Be careful in this step as the mixture will bubble. Stir the mixture constantly until the butter is melted.
Add in the heavy cream. Increase the heat to medium. Since the heavy cream is cold and the mixture is hot, it will appear as if the mixture will not combine. That is okay and normal. As the mixture heats up, it will combine.
Allow the mixture to bubble for 1 minute, without stirring.
Remove from heat.
4. Add caramel to cake pan and arrange apples. Line a 9-inch round cake pan with a piece of parchment paper on the bottom of the pan. Spray the bottom and sides with nonstick spray.
Pour the hot/warm caramel into the prepared 9-inch cake pan.
Arrange apple slices, starting around the outer edge and working your way towards the center. The apple slices will overlap slightly.
5. Preheat oven. Turn oven on and preheat to 350F.
6. Make cinnamon sugar filling and assemble cinnamon rolls. Punch the dough down and roll into a 10×24 inch rectangle.
In a medium sized bowl, stir together semi-melted butter, brown sugar and cinnamon. Spread mixture over dough, spreading all the way to the edges.
Roll dough up, starting at short end.
Cut the cinnamon rolls into 7 toughly equal cinnamon rolls. You may use either a piece of unflavored dental floss (my personal preference), or a serrated knife (I feel this is harder to get clean cuts of dough).
7. Arrange the rolls and bake. Place cinnamon rolls around the edge of the pan, on top of the apples, with one roll in the center.
Place the round cake pan on top of a rimmed baking sheet. This is to catch anything that bubbles out of the pan as it bakes in the oven.
Bake in preheated oven for 25-35 minutes. The cinnamon rolls internal temperature should be 190F when they are done baking. The center roll will take a bit longer to bake than the outer rolls. If the outer rolls are getting a bit darker, you may loosely cover the outer rolls with aluminum foil as the center roll continues to bake.
8. Cool and flip. Allow the rolls to cool on a wire cooling rack for 10 minutes.
Place a large plate/your serving plate on top of the pan, then carefully flip the warm pan over. You may need to wear oven gloves if the pan is too hot.
Lift the pan up and off of the cinnamon rolls.
9. Make the icing. In a small bowl, stir together the softened cream cheese and powdered sugar. If the mixture is too thick, you can add a small splash of heavy cream or whole milk.
The icing is just to drizzle on top, so you don’t need much. If you want more icing, you can double the recipe.
Drizzle the icing over the rolls. Serve and enjoy!
- Prep Time: 25
- Rise Time: 60
- Cook Time: 30
- Category: Breakfast/Brunch
- Method: Oven
- Cuisine: American
