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I opened the bottle of your vanilla extract last weekend to bake some cookies and the difference in taste is extraordinary." – Judy

Perfect Pineapple Upside-Down Cake


I love fresh pineapple! The best part about my infatuation is that pineapple is really nutritious and also reduces inflammation and pain.*

Years ago I found a recipe from Cook’s Illustrated magazine for Pineapple Upside-Down Cake that made a big enough cake to fit a 10-inch cast iron frying pan. This recipe, with some simple adjustments in sweetening, works well with any fruit upside down cake. I thought I had posted this recipe  on our site a long time ago and was surprised when I couldn’t locate it. I also couldn’t find the recipe in my personal recipe collection. (Turns out it was there, hiding in plain sight.)

Panic mode struck. I did not want to lose the recipe. I finally located a “best of” recipe from Cook’s Illustrated and made the cake. I quickly realized that it wasn’t right. So back to searching. In the process I found the original recipe I wanted, another interesting variation on the cake and my original spin on the recipe I had wanted.

From the search, and with my changes, a new version of Pineapple Upside Down cake emerged: The PERFECT Pineapple Upside-Down Cake. When you make this recipe, I think you’ll agree that it’s special.

I personally far prefer fresh pineapple to canned but, if canned is what you like, go ahead. You can slice the pineapple however you choose. I like lots of pineapple and cram every nook and cranny with it. Add Maraschino cherries if you like. Or walnuts — or both. I like the addition of rum. I had golden rum but the flavor didn’t carry through as well as I like, so I now use Meyers’s dark rum.

While is cake is terrific served cold, I prefer warming it and served with vanilla ice cream or lightly sweetened whipped cream on the side or passed in a small bowl.


Perfect Pineapple Upside-Down Cake




11/2 cups unbleached all-purpose flour**

11/2 teaspoons baking powder

1/3 teaspoon salt (or to taste)

3 tablespoons cornmeal (I like polenta grind but use what you like)

1/2 teaspoon Rain’s Choice ground Vanilla Bean Powder

1/2 cup (8 ounces) unsalted butter

1 cup sugar

4 large eggs, room temperature and separated

2 teaspoons Rain’s Choice pure Vanilla Extract

2/3 cup pineapple juice or 1/2 cup pineapple juice and 2 tablespoons dark rum


6 tablespoons unsalted butter

3/4 cup packed brown sugar

Approximately 3 cups of pineapple slices cut into 3/8-inch thick slices (they don’t have to be perfectly even)

2 tablespoons dark rum (optional)

1 10-inch cast iron skillet


Preheat oven to 350 F.

Melt the butter in the skillet over medium heat. Add the brown sugar until the butter and sugar are well combined and slightly caramelized. Remove from heat and arrange the pineapple however you choose in the pan. Set aside.

Whisk flour, baking powder, cornmeal salt and vanilla powder together in a medium bowl and set aside.

In a medium bowl, cream the butter. Slowly add the sugar and beat for about 2 minutes, or until it’s light and fluffy. Beat in the yolks, one at a time and add vanilla.

Add the dry mixture and liquid, alternating in 3 batches. If you are using single-acting baking powder, whip the egg whites first, then blend the dry and liquid ingredients.

In a separate bowl, beat egg whites until stiff peaks form. Fold ¼ of the egg whites into the batter until well combined. Add the remaining egg whites and fold into batter until no white streaks remain. Pour batter evenly into the cake pan, and bake until top is golden brown and cake tester comes out clean (about 60 minutes).

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*For more information about pineapple as well as more recipes visit here.

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Patricia Rain
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One Response

  1. I always found pineapple to be tricky when it comes to making cakes. At least when I’m in the kitchen!!! But, besides being delicious when it’s ripe, it’s very nutritious as you pointed.

    I will definitely give it a try.

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