Pineapple Upsidedown Cake

By:  Raven Wing  •  5 years ago  •  12 comments

Pineapple Upsidedown Cake

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This is one of our family favorites. The recipe comes from my Paternal Great-Grandmother, and has been passed down to each new generation. I hope you enjoy it.



1/2 cup unsalted butter, melted
2/3 cup dark brown sugar (firmly packed)
1 small jar of Maraschino cherries
1  20 oz can of pineapple slices (rings)
1 tablespoon of pineapple juice


1 1/2 cups all-purpose flour
1 1/2 teaspoons baking powder
1/2 teaspoon salt
1/2 cup unsalted butter, softened
2/3 cup white sugar
2 eggs
1 teaspoon vanilla extract
3/4 cup milk


  1. Preheat the oven to 350 degrees F (175 degrees C).

     2. Melt butter and mix with brown sugar and pineapple juice and spread the mixture evenly in a well buttered 9 x 12 inch cake pan. Pat the pineapple very dry between several sheets of paper towel, and arrange it evenly on top of the sugar mixture.  Place a cherry in the center of each ring.

     3. Sift together flour, baking powder and salt.

      4. In a large mixing bowl, cream the softened butter with the sugar until the mixture is light and fluffy. Add the eggs, one at a time, beating well after each addition. Stir in the vanilla. Add the flour mixture in three parts alternately with the milk, beginning and ending with the flour mixture. Beat well after each addition. Spread the batter evenly into the prepared pan.

      5. Place the cake in the middle of the oven. Bake for 45 to 55 minutes, or until a tester or wooden toothpick comes out clean. Let the cake cool in the pan on a rack for 5 minutes. Run a thin knife around the edge, and invert the cake onto a plate. Serve the cake warm or at room temperature. 



Use boxed cake mix, such as white or yellow (follow cake mix directions). If I use a boxed cake mix I prefer French Vanilla cake mix. It gives the cake a richer, deeper flavor. 

Use crushed pineapple instead of the rings. I put the pineapple slices in the small food chopper, but, you can also use well drained canned crushed pineapple.

Add pecans or walnuts (crushed or halves) with the topping mix.

Use a 10" round skillet instead of a cake pan (cast iron works good) 



jrGroupDiscuss - desc
Raven Wing
Professor Participates
1  author  Raven Wing    5 years ago

You can try your own variations of fruit for the cake topping, but, make sure it is not too juicy or it will make the cake soggy.

Professor Silent
1.2  TTGA  replied to  Raven Wing @1    5 years ago

Super cake Raven.  I'm not usually big on cake but this one is definitely the exception.  My wife has found that it works really well if she puts a layer of crushed pineapple down besides the rings.  Makes the cake a bit moister but still not soggy.  Totally good.

The real secret to getting the pineapple upsidedown cake to turn out properly is in the flipping it over.

We've found that it helps to turn the platter over and set it on top of the cake pan.  Then, holding them together, flip them over quickly.  Once in the proper position, a few taps on the bottom of the pan with the handle of a knife will usually make the cake come loose.

Raven Wing
Professor Participates
1.2.1  author  Raven Wing  replied to  TTGA @1.2    5 years ago
We've found that it helps to turn the platter over and set it on top of the cake pan.  Then, holding them together, flip them over quickly.

Yes, that is what I do. Having tried various ways at first, I found that is the best way to do so that it helps prevent Ooops with the cake on the floor or spread all over the counter trying to turn it over on the platter. jrSmiley_78_smiley_image.gif

Trout Giggles
Professor Principal
2  Trout Giggles    5 years ago

I'm the only one who likes this cake. I would make it but then I would have to eat the whole thing.

Wait...am I really complaining about that?

Professor Silent
2.1  TTGA  replied to  Trout Giggles @2    5 years ago
Wait...am I really complaining about that?

My thoughts exactly.  We have a tradition that whoever has a birthday in our family gets to choose whatever kind of cake that they want (and whatever is made for dinner).  Mine is always this type of cake.

So it looks like I will give some to my elderly neighbors next door. : )

But gee, Kathleen, I'm sort of elderly and only 1,000 miles away.jrSmiley_101_smiley_image.gif

Raven Wing
Professor Participates
2.2  author  Raven Wing  replied to  Trout Giggles @2    5 years ago

I love it but it makes too much for me alone, so I take part of it and give the rest to my Granddaughter and her friends. No waste around here. (grin)


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