Pineapple Upside-Down Cinnamon Rolls

Last month I bake my first ever Pineapple Upside-Down Cake... in honor of my Grandma Betty - view post here.


This month I decided to make some cinnamon rolls upside down with pineapples and some fresh Cherry Rhubarb Jam - which I had just whipped up.


So, next time you plan on baking up your favorite cinnamon rolls - consider doing this:

Melt butter and put into cake pan or glass casserole dish. Arrange pineapple slices, cherries (which is traditional in Pineapple-upside down cake) or in my case, I used the Cherry Rhubarb Jam. Add some chopped nuts to fill in the gaps. I used a combination of pecan and hazelnut. When you make cake you also put in brown sugar, but I left that out since it is rolled into the cinnamon rolls.

Use your favorite dough recipe - enough for about 8 large rolls - (I'll include below the awesome recipe I used), roll out dough, fill with melted butter, brown sugar and cinnamon and cut into 8 equal slices.

Place these 8 slices right side up evenly over pineapple layer. Place into warm oven (not hot) just warm enough to get the dough to rise a second time. Should take about 30 minutes or less.

Here they are just risen and ready to bake, adjust oven temperature... (but beware - see I used this pan, and if you use one just like it - put some foil or another baking sheet below it to catch the drippings - other wise you are gonna end up with smoke and the loud annoying beeping of the smoke detector!)

Remove from oven and cool about 10 to 15 minutes. Then remove sides of cake pan (spring form) and put a large platter or pizza plate over the top (inverted) then flip it over or turn it over or whatever - you know what I mean. Then you may or may not need a spatula to slide everything back onto the rolls. I needed a spatula because it was a bit sticky... and I just rearranged the slices into place.

Ta-Da!

Now, grab a plate and fork and enjoy!

The Awesome Recipe:

Using this recipe adapted from uTry.It Philly Friendship Braided Bread

TangZhong Ingredients:
1/2 Cup Boiling Water
1/4 Cup Bread Flour


Bread Dough Ingredients:
1/2 Cup Warm Milk
1/2 Teaspoon Salt
3 Tablespoon Sugar
3 Tablespoon Melted Butter
1 1/2 Cup Bread Flour
1 1/3 Teaspoon Active Dry Yeast 

Filling Ingredients:

1 tablespoon melted butter

1/3 cup brown sugar

Generous sprinkling of cinnamon

Pineapple-Upside Down ingredients:

1 can pineapple slices

Cherries or Cherry Jam

Chopped Nuts

2 tablespoons melted butter

To Make The TangZhong:
Place bread flour in a small bowl, pour boiling water over the bread flour and stir quickly with a fork to combine until no lumps.
Wrap mixture (it'll be a very wet dough) with plastic wrap, form dough in ball/round shape and leave in refrigerator overnight.


To Make The Rolls:
1. Take out the TangZhong from the fridge at least an hour before use (I usually leave it on countertop until it's room temperature).
2. In a bread machine, pour in ingredient in this order, warm milk, TangZhong 湯種, salt, sugar, butter, bread flour and yeast. Set bread machine to dough setting according to its user menu.

In the meantime, prepare cake pan or glass casserole dish: melt 1 tbsp butter and coat the bottom of the pan. Place one pineapple slice in the center. Then place the other slices around. If the other 7 slices don't fit evenly in the pan, as it was with me, then slice them in half and arrange as pictures. Put a little cherry or jam in the hole of each pineapple. Chop some nuts and fill in the gaps. I used a combination of pecan and hazelnut but pecan is just fine.

3. When dough is ready, take it out from bread machine and punch it a few times to deflate it. Roll out into large rectangle. Spread with melted butter. Then spread brown sugar and sprinkle with cinnamon.

4. Roll it up into a log and cut equally into 8 slices. Place these slices over and evenly into the prepared pan. Place in warm oven for about 30 minutes to rise a second time.

5. After it has risen, bake at 175-C degrees for about 15-20 minutes. Then take out and cool till pan is easy to handle. Put a large plate over the pan and invert the pan over, flip it - turn it. The cinnamon rolls and pineapples should come out easily but if they don't, just arrange everything back as it should look. 

Makes 8 - serve warm!