Pineapple Upside Down Cake

Flavorful vanilla cake mix is poured over brown-sugar-coated pineapple slices to create sweet Pineapple Upside Down Cake! Studded with maraschino cherries and infused with pineapple juice, you will love this tropical-tasting cake.

Homemade Pineapple Upside Down Cake

Pineapple Upside Down Cake is one of my favorite desserts to make year-round. I make it in the summer because the tropical flavors are perfect for hot weather, but I also make it during the winter when I need to feel like I’m on the beach, enjoying the warm sun!

Regardless of what the weather is like, though, this homemade pineapple cake will always please a crowd, and it’s also a somewhat unique treat to serve. Rather than offering a slice of regular frosted vanilla cake (which, don’t get me wrong, I’ll never turn down!) you can serve a slice of vanilla cake decorated with caramelized fruit!

I’ll get more specific for you so you can see just how delicious this cake is. Pineapple upside down cake starts with juicy pineapple slices. Those slices are topped with maraschino cherries, covered in vanilla cake batter (yes this is a cake mix recipe, get excited!), and then the whole cake is baked until tender and golden-brown!

Invert this easy pineapple cake, and you’ve got a sweet dessert that everybody will want a slice of.

What You’ll Need

Ready to get started on this oh-so-delicious pineapple upside down cake? Good! Me too.

Here are the ingredients we’ll need to round up:

• Cake Mix: I like to use Duncan Hines Yellow Cake Mix, but you can use whatever vanilla cake mix that you like.
• Pineapple: I like to use canned pineapple slices because then I can use the leftover juice in the cake batter.
• Pineapple Juice: You’ll mix this in with the cake batter to infuse it with sweet pineapple flavor!
• Vegetable Oil: To add moisture to the cake batter.
• Eggs: To thicken and add moisture to the cake.
• Vanilla: For extra sweet flavor!
• Butter: Melt this before adding it to the cake batter.
• Brown Sugar: To caramelize the pineapple slices with.
• Maraschino Cherries: To add a pop of vibrant color!

How to Make Pineapple Upside Down Cake

Pineapple upside down cake is a breeze to whip together and bake. It won’t take you more than an hour to make, and the majority of that is baking time.

First you’ll prep the pineapple slices in butter and brown sugar, then you’ll mix the cake batter together. Pour the cake batter over the pineapple, bake, and then enjoy a slice of tropical cake!

Here’s the in-depth explanation of what to do:

Preheat Oven to 350°F: Then, in a small sauce pan, melt the butter. Pour the butter into into a 9 x 13 pan and sprinkle the brown sugar over the melted butter.

Add Pineapple Slices: Arrange the pineapple slices in the pan in nice little neat rows. Add 1 cherry in the middle of each pineapple slice.

Prepare the Cake Batter: In a mixer bowl, mix cake mix, pineapple juice, oil, eggs and vanilla on medium speed for about 2 minutes. Pour the cake batter into the pan over the pineapple.

Bake the Cake: Bake for 30-45 minutes or until a toothpick comes out clean. Let cook in the pan for 5 minutes. Invert onto your serving dish.

How to Get the Cake Out of the Pan

Don’t stress over this step – it’s really simple! All you have to do is wait for the cake to cool completely, and then hold a serving platter over the top of the cake tray. Flip the tray over – with conviction – when you’re ready, slowly ease it off the top (which was previously the bottom) of the cake, and voila! Enjoy. 🙂

I don’t think you’ll have to worry about the pineapple sticking to the tray because of all the butter, but if you’re nervous about that, tap the pan lightly before lifting to loosen the pineapple slices from the tray.

Tips for Success

If you couldn’t tell already, I’m totally in love with this cake. I love how the sweet vanilla combines with the tangy fruit… and did I mention the amazingness that is caramelized pineapple?

Okay good, just checking.

Before you go, I have a couple of tips on this pineapple upside down cake that will make it even easier to bake:

• Make Sure All Ingredients Are At Room Temp: All ingredients should be at room temperature, but specifically, make sure the eggs are at room temperature. This will ensure that your cake batter comes together and bakes properly and evenly.
• Don’t Grease the Bottom of the Cake Tray: You’re going to be adding butter to the bottom for the pineapples, so no need to add more grease!
• Dry the Pineapple Slices and Maraschino Cherries: Before baking, dry the pineapple slices and maraschino cherries. This will remove any extra moisture that could prevent the fruit from adhering to/settling into the cake batter.
• Serve Warm: You can eat this cake cold if you want to, but personally, I prefer it warm! Toasty pineapple on top of spongy vanilla cake is almost too delicious.
• Let the Cake Cool Before Flipping: I mentioned this before, but the reason behind the waiting is a) so the cake won’t fall apart, and b) so you don’t burn your hands.

Serving Suggestions

Eating pineapple upside down cake as-is is totally fine, but you can make some additions to it as well, if you like. Here are some of my go-to sides for this pineapple cake:

• Fresh Fruit: Since you’ve already added pineapples and cherries, you might as well bring some more fruit to the party! I like strawberries, raspberries, blueberries, etc.
• Ice Cream: A slice of warm pineapple cake with a scoop of vanilla ice cream is SO good.
• Whipped Cream: I know there’s already a cherry on top of this cake, but you could add whipped cream and another maraschino cherry on top of your slice if you want to – treat yourself! You deserve it.

How to Store Upside Down Cake

Pineapple upside down cake should be stored in the fridge in an airtight container for 3-4 days. To reheat, pop it back in the oven at 350 degrees and bake until warmed through.

Can I Freeze This?

You can definitely freeze this cake. Store any leftovers in an airtight container – or two – and freeze for 1-2 months. Thaw overnight in the fridge before reheating and eating!

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More Classic Baking Recipes

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• Easy Classic Biscotti
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• Peanut Butter Blossoms
• Classic Pound Cake
• Chocolate Chip Cookies