pineapple upside down cinnamon rolls

Overview

Recipe Name: Pineapple Upside-Down Cinnamon Rolls
Prep Time: 25 minutes
Cook Time: 30 minutes
Additional Time (Rising/Resting): 1 hour
Total Time: ~2 hours
Servings: 12 rolls
Difficulty: Moderate
Best For: Breakfast, Brunch, Dessert

These Pineapple Upside-Down Cinnamon Rolls are a tropical twist on two classic favorites: pineapple upside-down cake and homemade cinnamon rolls. The sticky caramelized pineapple topping is rich and buttery, while the soft, fluffy cinnamon roll dough is filled with warm spices and brown sugar. This hybrid treat is perfect for impressing guests at brunch or treating yourself on a cozy weekend morning.

Let’s get baking!

 Why You’ll Love This Recipe

• Two desserts in one – Combines the gooey topping of pineapple upside-down cake with soft, spiced cinnamon rolls.

• Perfect for sharing – This recipe makes 12 rolls, ideal for family brunches or holiday mornings.

• Make ahead option – Prep the night before and bake fresh in the morning.

• Customizable – Swap in other tropical fruits or add nuts for texture.

 Ingredients

For the Dough:

• 3 ½ cups all-purpose flour (plus extra for dusting)

• 1 packet (2 ¼ tsp) active dry yeast

• ¾ cup warm milk (110°F)

• ¼ cup granulated sugar

• 1 tsp salt

• ¼ cup unsalted butter, softened

• 1 egg

• 1 tsp vanilla extract

For the Filling:

• ½ cup brown sugar

• 2 tsp ground cinnamon

• ¼ cup unsalted butter, melted

For the Pineapple Upside-Down Topping:

• ½ cup unsalted butter

• ¾ cup brown sugar

• 1 (20 oz) can pineapple slices (reserve juice)

• Maraschino cherries (optional, for garnish)

 Equipment Needed

• Stand mixer with dough hook (optional but helpful)

• Rolling pin

• 9×13 inch baking dish or large round pan

• Mixing bowls

• Saucepan

• Knife or dough cutter

• Measuring cups and spoons

• Plastic wrap or kitchen towel

 Instructions

Step 1: Prepare the Dough

1. Activate the Yeast
   In a small bowl, combine the warm milk and sugar. Sprinkle the yeast on top and let it sit for 5–10 minutes until foamy. This means the yeast is alive and ready to help your dough rise.

2. Make the Dough
   In a large mixing bowl (or stand mixer), combine the flour and salt. Add in the softened butter, egg, vanilla extract, and the activated yeast mixture. Mix until a shaggy dough forms.

3. Knead the Dough
   Knead by hand on a floured surface for about 8–10 minutes or use a stand mixer with a dough hook for 5 minutes, until the dough is smooth and elastic. If it’s too sticky, add a tablespoon of flour at a time.

4. First Rise
   Place the dough in a greased bowl, cover with plastic wrap or a clean kitchen towel, and let it rise in a warm spot for about 1 hour, or until doubled in size.

Step 2: Make the Topping

While the dough is rising, prepare your delicious pineapple topping.

1. In a saucepan over medium heat, melt the butter.

2. Add the brown sugar and stir until smooth and bubbly (about 2–3 minutes).

3. Pour the mixture into a greased 9×13 inch baking dish, spreading it evenly across the bottom.

4. Arrange pineapple rings over the brown sugar mixture. You can overlap them slightly or trim them to fit more.

5. Place a maraschino cherry in the center of each pineapple ring if using. Set aside.

Step 3: Make the Filling

1. In a small bowl, mix the brown sugar and cinnamon.

2. Melt the butter separately.

3. Once the dough has doubled in size, punch it down and roll it into a rectangle approximately 16 x 12 inches on a lightly floured surface.

4. Brush the melted butter over the dough.

5. Sprinkle the cinnamon sugar mixture evenly on top.

Step 4: Roll and Slice

1. Starting from the long edge, roll the dough tightly into a log.

2. Using a sharp knife or dental floss, cut the log into 12 equal rolls.

3. Place the rolls gently on top of the pineapple topping in the pan, cut side up.

4. Cover with plastic wrap or a towel and let them rise for another 30 minutes, or until puffy.

Step 5: Bake

1. Preheat your oven to 350°F (175°C).

2. Bake the rolls for 25–30 minutes, or until golden brown and cooked through. The tops should be slightly golden and firm to the touch.

3. Let them cool for 5 minutes, then carefully invert the pan onto a large serving platter or tray.

Tip: Place the serving platter over the baking pan and flip both together quickly to prevent the gooey topping from spilling.

 Optional Additions and Variations

• Nuts: Add chopped pecans or walnuts to the filling or topping for extra crunch.

• Spices: Add a pinch of nutmeg or cloves to the filling for a spiced holiday flavor.

• Coconut: Sprinkle shredded coconut over the topping before adding the dough.

• Cream Cheese Icing: Want more indulgence? Drizzle with cream cheese glaze after baking.

 Make Ahead Instructions

You can make these rolls the night before:

1. Assemble the rolls as directed (including placing in the pan over the pineapple topping).

2. Cover and refrigerate overnight.

3. In the morning, remove from the fridge, let them come to room temperature (about 30–45 minutes), and bake as directed.

 Serving Suggestions

• Serve warm with a hot cup of coffee, tropical tea, or a mimosa.

• These are perfect for:

  • Weekend brunches

  • Mother’s Day

  • Easter mornings

  • Holiday breakfasts

 Recipe Tips

• Use room temperature ingredients for best dough texture.

• Don’t rush the rise – A warm, draft-free environment is key.

• Flip carefully – The topping will be hot and sticky after baking.

• Leftovers? Store in an airtight container in the fridge for up to 3 days. Reheat in the microwave for 20–30 seconds.

 Nutrition Information (per roll)

Note: Nutrition will vary depending on the specific ingredients and brands used. For a lighter version, you can use low-fat milk and reduce the sugar slightly.

 Final Thoughts

These Pineapple Upside-Down Cinnamon Rolls are more than just a delicious treat—they’re a conversation starter. They combine the tropical sweetness of pineapple and rich caramel with the comforting flavor of cinnamon rolls, making them unforgettable. Whether you’re entertaining guests or indulging in a weekend bake, this recipe delivers every time.