This is by far the most delicious cake I have ever made. Seriously! From the moment I started gathering ingredients to when it was put into the oven prep was a total of twenty minutes. It is easy, only a few steps and an honest no-fail every time. My favorite part has to be licking the spatula! As this was the first-time making Pineapple Upside Down Cake, I was unsure what to expect. However, this recipe is easy to follow and results in a deliciously scrumptious cake.

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Published August 10, 2021
Updated March 11, 2022
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What you will Need

I love to try new dessert recipes. Cakes, cookies, granola, pie, bars and even pop-tarts. When I first made this cake, I thought it was going to be so difficult. But Pineapple Upside Down Cake has very few steps to mess up. Having a stocked pantry also helps when you or your family want to make a delicious dessert. In our pantry, I try to always have baking powder, many sugar varieties, vegetable shortening, canned fruit and any seasonings and spices in bulk. When you go to make recipes with ingredients in bulk, the cost breakdown can be considerably less than buying those little jars.

The only tip to share is to mix the dry and the wet ingredients very carefully to avoid splashing onto the counter. There is no need to sift the dry ingredients together as they will be mixed for three minutes into the wet ingredients before being baked.

Another tip is to use either sliced pineapple or pineapple chunks. There was a time when our pantry only had crushed pineapple and we thought this would have been the best way to make this cake. The issue with crushed pineapple and this recipe is that the pineapple was too small and actually almost disappeared into the cake and had a very small pineapple taste. Using chunks or slices is the way to go in my opinion. Plus, having the look of the caramel on top of the pineapple slices or chunks just looks beautiful and super delicious compared to the crushed pineapple cake.

Pineapple Upside Down Cake Recipe

Ingredients for Pineapple Upside Down Cake

1/4 cup unsalted butter
2/3 cup brown sugar
1 1/3 cup flour
1/3 cup shortening
1/2 tsp salt
9 slices pineapple
9 cherries
1 cup sugar
1 1/2 tsp baking powder
3/4 cup milk
1 egg

Pineapple Upside Down Cake Directions

1. Heat oven to 350 degrees.
2. While oven is heating, place 1/4 cup butter in a 9-inch square pan and place it into the oven to fully melt. No need to grease the pan. You can also try to use a Bunt pan or any other size that you have. I like this square pan because it perfectly fits nine pineapple slices, or in this case pineapple chunks shaped like slices.

3. When melted, around 1-2 minutes, remove the pan from the oven and sprinkle 2/3 cup brown sugar evenly in the pan. Pack down slightly with the back of the measuring cup if desired. Adding the brown sugar to the butter will bake into a delicious caramel and the tops of the cherries and pineapple will have a crispy and moist caramel, while keeping the cake very moist.

4. Arrange nine pineapple slices in the pan in rows of three. I only had chunks, so I tried to make cute little circles. Frankly, the family will not even notice! Plus, the chunks are WAY bigger in depth and will give the cake a larger chunk inside of the cake batter. Yummm… Also, easier to eat when the pineapple isn’t in slices and needing to be cut.

5. Place nine cherries in the center of each pineapple slice. This is tricky for me because I am allergic to raw cherries and almond. Maraschino cherries are in almond extract, so I cannot eat them. For that matter I cannot put them on the entire cake for risk of an ER visit. No one has time for that! At least not THIS week.
Click for an article on WebMD Nourish about the history of maraschino cherries.
WebMD Nourish is not a sponsor for this post

6. In the KitchenAid mixing bowl, beat all of the remaining ingredients for three minutes, including 1 1/3 cup flour, 1/3 cup shortening, 1/2 tsp salt, 1 cup white sugar, 1 1/2 tsp baking powder, 3/4 cup milk and 1 egg.

Be careful as you turn on the mixer as the milk will want to splash out of the mixer onto your countertop. How is it that when I use my KitchenAid with blending dry ingredients that they overflow onto the counter. Do you have this happen also? If your KitchenAid has the splashguard, try using that with this recipe as it can help to keep your ingredients inside the bowl while mixing.

7. Carefully pour the mixture over the pineapples and then spread it evenly with a spatula.
I love my Rachel Ray spatula set because they are sturdy and have three different sizes: perfect for scraping the bowl and smoothing out the cake batter.

8. Bake for 50-55 minutes. I typically bake this cake around 53 minutes because it stays more moist and the caramel tends to be more liquid and delicious. Any longer than 55 minutes and the top of the cake, when you flip it over, is a harder caramel. Our family loves the amount of moist caramel that this cake keeps on the top.

9. When the cake pan is removed from the oven, immediately place the heated pan on a platter, then carefully flip the pan onto the platter. Then, remove the pan from off of the cake. However, do not make my mistake, flip the pan onto a platter that is bigger than, or the same shape, as your pan to avoid a sad mess.

10. Let the cake rest for 3-5 minutes before serving. The brown sugar and butter caramelize and will be screaming hot! It will be difficult to wait to eat this and you will want to skip dinner, so make it ahead of time so you do not have to wait too long for it to cool. When you slice into the cake, you can see how the pattern of the pineapple is perfectly measured out to have this cake serve nine. So, each person gets a beautiful circle of pineapple and a cherry in the middle. How pretty is that?!

Pineapple Upside Down Cake Recipe

Ingredients

1/4 cup unsalted butter
2/3 cup brown sugar
1 1/3 cup flour
1/3 cup shortening
1/2 tsp salt
9 slices pineapple
9 cherries
1 cup sugar
1 1/2 tsp baking powder
3/4 cup milk
1 egg

Directions for Pineapple Cake

1. Heat oven to 350 degrees.
2. Place 1/4 cup butter in a 9-inch square pan and then place the pan into the oven to melt.
3. When melted, sprinkle 2/3 cup brown sugar evenly in the pan and then pack the sugar down slightly.
4. Arrange 9 pineapple slices in the pan in rows of three.
5. Place 9 cherries in the center of each pineapple slice.
6. Then, in a KitchenAid mixing bowl, beat all of the remaining ingredients for three minutes which includes the flour, shortening, salt, white sugar, baking powder, milk and 1 egg.
7. Carefully pour the cake batter over the pineapples and then spread it evenly with a spatula.
8. Finally, bake the Pineapple Upside Down Cake for 50-55 minutes.
9. When the cake pan is removed from the oven, immediately place the heated pan on a platter, then carefully flip the pan onto the platter. Then, remove the pan from off of the cake.
10. Let rest for 3-5 minutes before serving.

Enjoy!
~Monica

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