We are big fans of pineapple upside down cake. The bottom is buttery, and it’s full of brown sugar that gets caramelized with a pineapple to create an incredible flavor. We wanted to make that same base but then, instead of the classic cake, put our milk bread cinnamon rolls on top. This combination gives you the best of a pineapple upside down cake and soft cinnamon rolls, creating our pineapple upside down cinnamon rolls.

Why You’ll Love These Milk Bread Cinnamon Rolls

By using the Tangzhong method (a Japanese method that cooks flour and water together), these rolls stay soft for a few days. Also since these are like a pineapple upside down cake, when you flip the pan, the brown sugar and butter create a glaze, so there is no frosting needed. It’s the perfect brunch item for the holidays or a special occasion.

The Best Pineapple Upside Down Cinnamon Rolls (Milk Bread Recipe)

Prep Time 1

Total Time 1

Servings 12

Ingredients

Pineapple Upside Down Cake Base:

1 stick salted butter 113 g
1 cup brown sugar
6 maraschino cherries cut in half
12 rings of canned pineapple pressed dry

Milk Bread Cinnamon Rolls:

Tangzhong

200 g water
40 g bread flour

Dough

1 cup milk
4 tablespoons milk powder 24 g
2 packs active dry yeast 14 g
700 g bread flour ~5 cups
1/2 cup granulated sugar 100 g
2 teaspoons salt
2 large eggs
1 stick softened butter 113 g

Filling

1 stick butter softened 113 g
2 tablespoons cinnamon
1 cup granulated sugar 200 g
1 teaspoon vanilla or 1 tablespoon vanilla bean paste

Instructions

Tangzhong:

Add the flour and water into a medium saute pan over medium heat. Stir to combine.
Continue to stir with a spatula until it forms a thick paste (about 5 minutes)
Refrigerate the mixture for at least 4 hours (up to overnight). An hour before use, take the paste out of the fridge to bring it to room temperature

Milk Bread Dough

Blooming the yeast:

To bloom the yeast, add together warm milk, 1 tablespoon of sugar, and the yeast into a small bowl. The milk should be about 105 degrees fahrenheit. Let the mixture sit for 5 minutes until it is slightly sweet smelling a bubbly.

Making the dough

In the base of a stand mixer fitted with a dough hook, add the bread flour, milk powder, salt, and remaining sugar. Run the mixer on low and add in the bloomed yeast, egg, and tangzhong. Mix for about 2-3 minutes on low until the dough begins to form.
After 2-3 minutes add in the softened butter and continue to mix on low for about 1 minute. After the butter is incorporated, increase the mixer speed to medium high and mix for 8 minutes. At this point the dough should form a ball that is not too sticky, if it is not forming a ball, add in a few more tablespoons of bread flour.
Once the dough is smooth and formed into a ball, place it into a greased mixing bowl. Cover the bowl with a towel and proof it for about 1 hour or until it has doubled in size (the time this takes will depend on the temperature of where you are letting the dough proof)

Prepare the pans:

Prepare 2 9×13 inch pans by pouring ½ a stick of butter in each pan and spreading it into an even layer. Sprinkle ½ cup brown sugar in each pan to form an even layer.
Add 6 pineapple rings into each pan, placing them in 3 rows with 2 each as this will be the base of your roll. Place ½ a maraschino cherry inside each pineapple. Set aside

Shaping:

After the dough has doubled in size. Flour the counter or a large surface and roll it into a rectangle (about ¼ inch thick)
Make the filling by mixing softened butter, cinnamon, and sugar. After the filling is mixed, spread it over the dough leaving a ½ border along the edges
After adding the filling, roll the dog into a log rolling the longer side inwards until a tight log forms.
Once the roll is formed used unflavored floss or a knife to cut the dough into 12 pieces (We cut off the ends and then cut 12 even pieces)
Place 6 pieces of dough in each pan in the center of the pineapple ring, cut side down. Cover the pans with a kitchen towel and let them proof for about 45 minutes or until they have almost doubled in size.
Preheat the oven to 350˚F
After they have proofed, bake the cinnamon rolls for ~35 minutes or until they are golden on the edges but baked in the center and on the bottom.