Pineapple Upside Down Cake

Pineapple cake

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.

Monica holding a blue spatula in kitchen

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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

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

ingredients for Pineapple Upside down Cake
All of the ingredients you will need for this recipe.

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.

brown sugar mixed in melted butter for pineapple upside down cake topping
Spread the brown sugar evenly on the melted butter.

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.

pineapples arranged in brown sugar in baking pan
When in a pinch, chunks work just as well as pineapple slices.

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

cherries placed in center of pineapple for upside down cake design
Doesn’t this pattern look so pretty!

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. The price will likely change over time, so click this link to check the current price of Rachael Ray Tools & Gadgets on Amazon.

pineapple upside down cake batter pouring on top of pineapples and cherries


Pour the cake batter on top of the pineapple and CAREFULLY spread it to not disturb the design.

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.

pineapple upside down cake unbaked in baking pan

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?!

slice of pineapple upside down cake on a plate
The butter caramelizes so amazing with this cake!

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

A few of my favorite things

Published by Monica's Scratch Kitchen

I have not always had the skills to cook and bake from scratch. As a young wife, I bought every meal frozen or boxed and presented it to my husband with a flourish, believing myself a decadent cook. As our budget shrunk, and our family grew, I looked for ways to stretch our money to nourish our kids with the best for their hungry appetites. Hoping to find recipes and meals that they would love to eat. Through the last 5 years, I have learned so many cooking and baking lessons, and experienced many wins and failures. Come along with me on this journey as I share my recipes that work, how to make them on the cheap, and my tips and tricks to get my kids to eat homemade deliciousness! I will also share updates to our house that we have done in the last year since our move. With one income, we do most of the work ourselves and with amazing family and friends to help out, cutting costs but keeping style and money in the bank! I am a wife and mother of 3 boys and 1 princess. When I was a kid, I remember being asked what I wanted to be or do when I grew up. My response was, "a mom", and I am proud to grow up and be a mom to 4 amazing kids! Samuel is 11, Matthew is 8, Levi is 4, and Elliana is almost 2. We have been blessed to have kids who love to explore foods, to try new recipes, and enjoy helping us around the house. With 4 kids, you better believe they help clean! My husband Tyler and I have been married almost 13 years. We love our kids, we love outdoors, camping, canoeing, grilling, watching movies, and just hanging out making memories. A few years ago I gifted Tyler with his own "menu" book, where we write meals and foods we have loved to eat. Weekly our family decides what our meals will be and I make up a grocery list with what we need. It literally is my favorite chore! I love to shop, so shopping for food on a budget is my biggest win! Thank you for taking the time and visiting my site, Subscribe so you do not miss a post! Keep coming back to hear about new recipes, updates on our home, fun times with our kids, and how to make homemade deliciousness! ~Monica

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