Pineapple Upside Down Cake

This recipe for homemade Pineapple Upside Down Cake is a must try! A soft, moist, white crumb cake with pineapple juice is baked inside a cake pan with pineapple ring slices, maraschino cherries, and topped with a sweet brown sugar caramelized glaze. So good and a classic dessert that you must try. 

For more pineapple recipes be sure and try my Easy Pineapple Pistachio Cake, my super moist Orange Pineapple Cake, and this Pineapple Chicken Salad recipe. 

Pineapple Upside Down Cake Recipe

Pineapple Upside Down Cake is a classic dessert recipe. Today I’m sharing this homemade version with a soft, moist vanilla cake base, topped with pineapple rings and maraschino cherries, and then finished off with a brown sugar caramelized glaze on top. 

This cake has extra flavor because it uses some of the pineapple juice, from the can, to make the white cake. 

Upside down cakes are so fun to make because they bake upside down and then you flip it over to show off that gorgeous pineapple and cherry topping!

Ingredients Needed

Here are the ingredients that you will need to make a pineapple upside down cake, from scratch, in your own kitchen. I also share a few tips so that you can easily recreate it. There are a couple different steps, so it may look like a lot but really most the ingredients are shared or similar. 

• Pineapple Brown Sugar Glaze
  • Light Brown Sugar
  • Butter
  • Pineapple Juice – Use some of the juice from the can of pineapple rings.
  • Pineapple Rings
  • Maraschino Cherries
• Cake
  • All-Purpose Flour
  • Granulated Sugar
  • Baking Powder – Helps the cake rise while baking.
  • Table Salt – This is just regular, iodized table salt. 
  • Baking Soda
  • Large Eggs
  • Buttermilk – I don’t recommend using a buttermilk substitute for this recipe. I find that regular buttermilk purchased from the store is better to use when baking. 
  • Pineapple Juice – Again, use some pineapple juice from the can of pineapple rings. 
  • Butter
  • Vanilla Extract

How To Make Homemade Pineapple Upside Down Cake

Learn how to make this cake recipe with the simple steps below. Be sure and read to the bottom of the page where there is a printable recipe card, a pin it button so you can save it to Pinterest, and the detailed ingredients and directions needed for this recipe. 

• Preparation : Heat the oven to 350 degrees F. Spray a 9-inch or 10-inch round cake pan with cooking spray. Set aside. 
• Pineapple Brown Sugar Topping : Add the brown sugar, butter, and pineapple juice into a saucepan, over medium-high heat, and heat just until melted and sugar is dissolved. Pour this into the cake pan. Place a pineapple ring in the center and then cut 5 pineapple rings in half, so you’re left with a half moon shape. Place them around the middle pineapple ring all facing the same direction. Press a maraschino cherry into the middle of each pineapple ring. 
• Pineapple Vanilla Cake : Prepare the cake according to the directions. Dollop spoonfuls of the batter on top of the pineapple rings and then gently spread it out. Be careful as not to mess up the pineapple layer of brown sugar mixture. 
• Cook : Bake in the oven for 35-45 minutes or until a toothpick inserted into the middle comes out clean. Let the cake cool in the pan for 20 minutes before inverting it onto a serving platter. Cut into slices like you would a pie and serve. 
• Serve : Serve a slice of cake topped with whipped cream (homemade or from a spray can) and a cherry on top!

Tips For Success

Here are a few of my helpful tips so that you can have success recreating this recipe in your own kitchen. 

• Cake Pan : This recipe has been tested with a 9-inch round cake pan. Do not use anything smaller than that size. I promise, it will be too small and the cake batter will spill over while baking. You can use a 10-inch round cake pan if that’s what you have. 
• Melted Butter : The best way to get melted but slightly cooled butter is to microwave the butter for about 30 seconds. You will have half melted + half soft shaped butter at the end of that time, stir with a fork until it’s all completely melted smoothly together. You are now able to use it immediately. Doing it this way, prevents the butter from getting so boiling hot in the microwave because you’re not melting it fully. 
• Tent With Foil : Towards the end of the cook time, if the cake is getting too browned on top then loosely lay a piece of tin foil over top the cake. 
• Let the Cake Cool : Be sure and let the cake cool inside the pan for at least 20 minute before inverting it onto a serving platter. It needs time to come together and for the brown sugar glaze to set up slightly before inverting it onto a platter. 

Pineapple Upside Down Cake FAQ’s

• How to Store Leftovers
  • Leftovers can be stored at room temperature, in a covered container, for up to 3 days. 
  • You can also store leftovers in the fridge for up to 1 week. Storing it in the fridge will make the cake dry out slightly so you may want to warm it up before eating. 
• Can I Freeze Pineapple Upside Down Cake?
• Serving Suggestions
  • This is best served with a dollop of whipped cream on top (either store-bought from a spray can or homemade whipped cream) and an extra cherry on top. 
  • It can be served cooled completely to room temperature or serve it slightly warm. Slightly warm as in after the 20 minute cooling time. 
• Can I Make It Ahead of Time?
  • I would recommend making this just a few hours before you need it. It won’t keep well out at room temperature for a long period of time before serving. The brown sugar will make the cake softer, so instead of that caramelized glaze texture it will be soft. 
  • If I am serving this for dessert after dinner, or taking it somewhere, I always plan on making it 2-3 hours ahead of time. 

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