Fresh Pineapple Upside Down Cake is a classic cake we will always love.

Sharing an oldie but a goodie today: Pineapple Upside Down Cake, only for this recipe we are using fresh pineapple rather than pineapple from a can, because it’s better! We’ve made this as two 8inch round cakes and as 24 cupcakes. If it’s been a few years since you’ve had this cake, you need to make it again real soon…you forget how good it is! Topped with freshly whipped cream, it’s the perfect dessert to brighten a cloudy day. Plus fresh pineapples are easy to find this time of year. We had it the other night, and it’s always a favorite!

What you’ll need to make Fresh Pineapple Upside Down Cake or cupcakes:

butter
brown sugar
fresh pineapple
maraschino cherries
yellow cake mix
oil
eggs
whipped cream (for serving)

How to make Pineapple Upside Cupcakes:

Here’s the instructions for making 24 cupcakes, below you’ll find the instructions for making two 8-inch rounds.

Preheat your oven to 350 F. Grease the cups of two cupcake pans.
Prepare the pineapple: cut the pineapple into chunks (discard the top, bottom and center core).
Prepare the cake mix batter: as directed on the box, mix together the cake mix.
Mix together the butter and brown sugar: Melt the butter in the microwave. Add the brown sugar to the butter and mix the two together.
Add 1 teaspoon of the butter brown sugar mixture to the cups of both cupcake pans. You will most likely have excess of this mixture.
Place 3-4 chunks of pineapple into each individual cup, onto of the butter brown sugar mixture.
Using an ice cream / cookie scoop, add the cake batter to each cup over the pineapple chunks and the butter brown sugar mixture.
Bake: Bake for 18-21 minutes or less. Insert a toothpick to check for doneness. If the tooth pick comes out clean, you know the cake is done.
The upside down flip: To serve the cupcakes, carefully run a knife around the edge of each individual cupcake. Using a spoon, carefully lift each one out of the pan and move them to a serving plate. Scrap out any excess caramel and spoon over the top of the cupcakes.
Serve: Serve warm with sweetened cold whipped cream.

How to make Fresh Pineapple Upside Down Cake using a cake mix:

These are the instructions for making two 8-inch rounds:
Preheat your oven to 350 F. Grease two 8-inch cake pans.
Mix butter and sugar: Melt the butter in the microwave. Add the brown sugar to the butter and mix the two together.
Pour mixture: Pour the butter brown sugar mixture evenly into the bottom of two greased 8-inch round cake pans (or one 9×13 pan).
Assemble fruit: Place pineapple rings and maraschino cherries into the bottom of the pan in a decorative pattern.
Make cake mix: Prepare the cake mix batter as directed on the box. Gently pour the cake batter over the pineapple and cherries.
Bake: Bake for 35 – 40 minutes or less. Insert a toothpick to check for doneness. If the tooth pick comes out clean, you know the cake is done.
Flip and scrap: To serve the cake, run a knife around the edge of the cake. Place a plate wider than the pan over the top of the pan, and with two hands flip the cake over onto the plate. Scrap out any excess caramel over the top of the cake.
Serve: Serve warm with sweetened cold whipped cream.

Making your Pineapple Upside Down Cake pretty:

One fun thing about making this cake is that you can place the fruit in any design or shape you want! We did a more simple one, and then we made a cute smiley face on one. You can get creative with it. You can cut the pineapple into chunks or leave them in rings. It’s really up to you. Have fun with it!

How to prevent soggy Pineapple Upside Down Cake:

No one wants their cake to turn out soggy. One way to prevent this is to remove excess liquid off of the fruit before laying it into the bottom of your pan.

Fresh vs. Canned Pineapple:

Because fresh pineapple is readily available year round, we love to make it with fresh pineapple, but we have made this recipe with both fresh and canned pineapple. Fresh pineapple really is better. We like the texture of fresh pineapple better than canned pineapple. The trick with using fresh pineapple is to make sure that the fresh pineapple is ripe, but not under ripe. The cake will not be as good if the pineapple is green, hard and underripe. Fresh pineapple really does make it so delicious. If you cannot find perfectly ripe fresh pineapple, canned pineapple is also a great option, just make sure to buy canned pineapple in the juice, not in syrup.

Variations:

Rather than adding the maraschino cherries into the baked cake, you can serve the cake with maraschino cherries. Just make sure to buy the maraschino cherries with stems attached. They look better for serving.
Add the pineapple in ring slices if making two cakes OR add the pineapple into the bottom of the pan cut into pineapple chunks if making 24 cupcakes.
Use canned pineapple rings or fresh.
If using fresh pineapple, and you want to add pineapple juice into the cake batter, but you don’t have enough juice from the fresh pineapple, you can blend a 20oz. can of crushed pineapple. You only need one cup for the cake batter, so you can just freeze any excess to be used in smoothies later.
Serve warm or cold

Tips and Tricks:

As with all cakes, avoid over baking the cake. Use a toothpick to check the bake for doneness. When the toothpick comes out clean, it’s ready.
The perfect Flip: When flipping this cake over, you always cross your fingers the cake will exit the pan with ease. To make sure that this happens, you will want to grease your pans before adding the butter brown sugar mixture. You could also line with parchment paper to fit your pans for more insurance.
Avoid adding too much excess fruit juice from the pineapple and maraschino cherries to keep the cake from getting soggy.
If serving with whipped cream, you will want to let the cake cool a bit so the whipped cream doesn’t melt on the plate the second its served.

How to choose a good ripe Pineapple:

To pick a good ripe pineapple, choose one by the scent on the bottom of the pineapple, it should have a good fresh pineapple scent. Another way to help tell if it’s ripe, the color of the pineapple exterior will be yellow, and the very center leaves should easily pull out. Avoid choosing a green, hard and under ripened pineapple for this recipe.

How to store Fresh Pineapple Upside Down Cake:

Once baked, Pineapple Upside Down Cake can be flipped out of the baking pan and onto a plate. If making ahead, and serving it cold, it can chill in the fridge covered lightly with plastic wrap until you are ready to serve. Keep the whipped cream stored separately if planning to serve it warm. Any leftover cake can be stored in the fridge. It will keep up to 3 days!

Do you Serve Pineapple Upside Down Cake warm or cold?

We love this cake served warm, but if you need to make it ahead, you can serve it cold and keep it chilled in the fridge covered lightly with plastic wrap, and pipe the whipped cream and cherries on top (if making cupcakes). If serving warm, just add the whipped cream off to the side so that it doesn’t instantly melt to a puddle.

Fresh Pineapple Upside Down Cake

Pineapple Upside Down Cake using fresh pineapple, and a yellow cake mix because why not?! Make this recipe with two 8-inch rounds or 24 cupcakes.

Course Dessert

Author Kami | NoBiggie.net

Ingredients

1/3 cup butter melted
1 ¼ cup packed brown sugar
½ fresh pineapple rind removed, sliced and core removed (may use 20 oz. can pineapple rings and juice in cake mix)
Maraschino cherries drained
1 box yellow cake mix mixed according to directions with oil and eggs but substitute pineapple juice for water (if using canned pineapple)

Instructions

Instructions for two 8-inch round cakes:

Preheat your oven to 350 F. Grease two 8-inch cake pans.
Melt the butter in the microwave. Add the brown sugar to the butter and mix the two together.
Pour the butter brown sugar mixture evenly into the bottom of two greased 8-inch round cake pans (or one 9x13 pan).
Place pineapple rings and maraschino cherries into the bottom of the pan in a decorative pattern.
Prepare the cake mix batter as directed on the box. Gently pour the cake batter over the pineapple and cherries.
Bake for 35 - 40 minutes or less. Insert a toothpick to check for doneness. If the tooth pick comes out clean, you know the cake is done.
To serve the cake, run a knife around the edge of the cake. Place a plate wider than the pan over the top of the pan, and with two hands flip the cake over onto the plate. Scrap out any excess caramel over the top of the cake.
Serve warm with sweetened cold whipped cream.

Recipe Notes

Instructions for making cupcakes:
Preheat your oven to 350 F. Grease the cups of two cupcake pans.
Prepare the pineapple: cut the pineapple into chunks (not rings)
Prepare the cake mix batter: as directed on the box, mix together the cake mix.
Combine the butter and brown sugar: Melt the butter in the microwave. Add the brown sugar to the butter and mix the two together.
Add 1 teaspoon of the butter brown sugar mixture to the cups of both cupcake pans. You will most likely have excess of this mixture.
Place 3-4 chunks of pineapple into each individual cup, on top of the butter and brown sugar mixture.
Using an ice cream / cookie scoop, add the cake batter to each cup over the pineapple chunks and the butter brown sugar mixture. Fill each cup 2/3rds full.
Bake: Bake for 18-21 minutes or less depending on your oven. Insert a toothpick to check for doneness. If the tooth pick comes out clean, you know the cupcakes are done.
To serve the cupcakes, carefully run a knife around the edge of each individual cupcake. Using a spoon, carefully lift each one out of the pan and move them to a serving plate. Scrap out any excess caramel and spoon over the top of the cupcakes.
Serve: Serve warm with sweetened cold whipped cream and a maraschino cherry on top or serve with vanilla ice cream.