Pineapple Upside-Down Cake

After a series of trial and error, I finally am ready to present to you the best easy pineapple upside-down cake from scratch!  Made with a soft, fluffy, and simple vanilla cake recipe that uses only the most basic ingredients and a pretty topping of caramelized pineapple and maraschino cherries, this classic recipe is slated to be a staple in your baking repertoire.  

If you follow my Instagram stories, you might be tired of seeing this pineapple upside-down cake already.  That’s because it took me so many times to get it right, and every time I thought I nailed it, I shared it on Instagram, and then it turned out that I hadn’t quite turned out like I’d hoped, after all.

Sorry about that.

It was the fluffy vanilla cake layer that was so difficult.  The pineapple and cherry top (/bottom?) is the easy part, it’s just a matter of combining melted butter and brown sugar in a pie plate and assembling your fruit, but a well-suited vanilla cake was much trickier to get right.

Can you believe that my biggest problem was that my cake started out being much too moist?

I wanted a vanilla cake that was reliable and would come out right every time, I needed it to be fluffy and soft, but it also needed to be sturdy enough that it could handle a little bit of weight on top once it was inverted, and not so moist that it absorbed all of the juices from the fruit, leaving you with a soggy sponge for a cake.

Doesn’t seem so difficult, but it took about 8 attempts to get right.

After some experimentation with eliminating the buttermilk and sour cream that I had been using in my recipe (and getting a bit friendlier with the baking powder than I initially was comfortable with), I finally achieved a stable, versatile vanilla cake layer that paired perfectly with the fruit topping and was not at all sponge-y.

The best part is that this vanilla cake recipe calls for only the most basic ingredients, making for an extremely easy pineapple upside down cake.

The final result was perfection ^^^

In anticipation of a question I get asked frequently about inverting cakes, I wanted to address the best way to flip your pineapple upside-down cake. Trust me, it’s extremely simple, but since the inversion part is so critical to this pineapple upside-down cake, I wanted to address that here, but I’m sorry if this seems too rudimentary to you!

How do I flip a pineapple upside-down cake?

1.  Allow your pineapple upside-down cake to cool for 10-15 minutes before you attempt inversion.  If any of the cake has baked into  the edge of your pie plate or cake pan, you can use a knife to gently loosen the edges and free them from the pan.
2. Place your cake platter (or any plate that’s larger than your pineapple upside-down cake) over the pan — plate surface should be facing your vanilla cake layer.
3. Using oven mitts carefully and firmly grip both the side of the cake platter and the cake pan on either side.
4. Carefully but quickly flip everything over so that the bottom of the cake pan is facing upwards, and then set down your cake platter and carefully remove the cake pan (careful, it will still be hot!)

And that is it!  This cake tastes best warm, so while you still want it to cool a bit, I don’t recommend waiting too long to dig in!

Enjoy!

4.75 from 4 votes

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Pineapple Upside Down Cake

A classic pineapple upside down cake recipe to save for years to come!

Prep Time 25 minutes

Cook Time 45 minutes

Total Time 1 hour 10 minutes

Servings 8 slices

Calories 335 kcal

Author Samantha Merritt

Ingredients

Topping

• 1/4 cup butter melted (60g)
• 1/2 cup brown sugar tightly packed (100g)
• 10 pineapple rings/slices patted dry
• maraschino cherries

Vanilla Cake

• 1/2 cup butter softened to room temperature (115g)
• 3/4 cup sugar (150g)
• 2 eggs room temperature preferred
• 1 teaspoon vanilla extract
• 1 1/2 cups all-purpose flour (195g)
• 1 1/2 teaspoons baking powder
• 1/4 teaspoon salt
• 1/2 cup milk room temperature preferred (120ml)

Instructions

1. Preheat oven to 350F (175C)

2. Pour melted butter into 9" pie plate or deep cake pan, make sure it entirely covers the bottom of the pan and use a spoon or spatula to grease the sides of the pan.

3. Sprinkle brown sugar evenly over butter mixture.  Arrange pineapple slices over the bottom of the pan, slice leftover slices in half and arrange up the sides of the pan, as seen in photo.

   

4. Place cherries in center of pineapple rings and as desired in empty spaces.  Set aside.

5. To prepare vanilla cake, beat butter and sugar in medium-sized bowl until creamy and well-combined.  

6. Add eggs, beating one at a time until combined.  

7. Stir in vanilla extract.

8. In a separate bowl, whisk together flour, baking powder, and salt.  

9. Alternate adding flour and milk, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to overmix).

10. Pour batter evenly over prepared cake pan and pineapple/cherry layer.  

11. Bake on 350F (175C) for 30 minutes.  At the 30 minute mark, loosely cover with foil and continue to bake (still on 350F/175C) for another 15 minutes, until a toothpick inserted in the center comes out mostly clean with few crumbs (total cook time for cake will be 45 minutes).

12. Allow to cool for 10-15 minutes and then carefully invert cake onto serving platter (careful, it will still be very hot!).

13. Allow to cool before cutting and enjoying, but don't wait too long as this cake tastes wonderful (best!) warm from the oven!

Nutrition Facts

Pineapple Upside Down Cake

Amount Per Serving

Calories 335

* Percent Daily Values are based on a 2000 calorie diet.

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