Pineapple Upside-Down Cake

Name: Pineapple Upside-Down Cake
Total time: 1 h 30 min
Yield: 8 to 12 servings
Cuisine: american
Ingredients: 1/2 cup/110 grams packed light or dark brown sugar; 1/4 cup/57 grams unsalted butter, melted and still hot; 1/2 teaspoon pure vanilla extract; 1/4 teaspoon ground cinnamon (optional); 1 (20-ounce/567-gram) can pineapple slices, drained; 15 to 20 maraschino cherries, stems removed; 2 cups/256 grams cake flour, sifted; 1 teaspoon baking powder; 1/2 teaspoon baking soda; 1 teaspoon coarse kosher salt; 1/2 cup/113 grams unsalted butter, at room temperature; 1 cup/200 grams granulated sugar; 2 large eggs, at room temperature; 1/3 cup/93 grams plain Greek yogurt, at room temperature; 1 teaspoon pure vanilla extract; 1/2 cup/120 milliliters whole milk, at room temperature

By Millie Peartree

Published May 25, 2022

Pineapple Upside-Down Cake — Armando Rafael for The New York Times. Food Stylist: Simon Andrews.

Total Time: 1½ hours
Rating: 4(654)
Comments: Read comments

This Southern staple is the kind of cake that’s always on the table, ready to greet anyone who comes over. Good enough for dessert, it’s also not supersweet, so you could have it for breakfast with coffee or tea, or at any time of day. Made with canned pineapple and maraschino cherries (which can stay in the cupboard for a long time), it’s a delicious and beautiful cake that’s also budget friendly. The caramel finish is simple to put together, and the base is light and moist, but strong enough to hold up that joyful topping. If you don’t want to use whole milk, you could use an equal amount of the reserved pineapple juice. The end result will be slightly sweeter, but that’s not a bad thing.

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Ingredients

Yield:8 to 12 servings

For the Topping

½cup/110 grams packed light or dark brown sugar
¼cup/57 grams unsalted butter, melted and still hot
½teaspoon pure vanilla extract
¼teaspoon ground cinnamon (optional)
1(20-ounce/567-gram) can pineapple slices, drained
15 to 20maraschino cherries, stems removed

For the Cake

2cups/256 grams cake flour, sifted
1teaspoon baking powder
½teaspoon baking soda
1teaspoon coarse kosher salt
½cup/113 grams unsalted butter, at room temperature
1cup/200 grams granulated sugar
2large eggs, at room temperature
⅓cup/93 grams plain Greek yogurt, at room temperature
1teaspoon pure vanilla extract
½cup/120 milliliters whole milk, at room temperature

Ingredient Substitution Guide

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Preparation

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Step 1
Heat oven to 350 degrees.
Step 2
Prepare the topping: In a medium bowl, whisk together sugar, butter, vanilla extract and cinnamon (if using). Pour the mixture into an ungreased 9-inch pie dish or round cake pan that’s at least 2 inches deep.
Step 3
Using a clean kitchen towel or a paper towel, blot any excess liquid off the fruit. Arrange the pineapple slices to your liking in a single layer on top of the brown sugar-butter mixture, covering the base of the pan, then add the cherries wherever there’s a gap. Place the pan in the refrigerator while you prepare the rest of the cake.
Step 4
Prepare the cake: In a medium bowl, whisk together the cake flour, baking powder, baking soda and salt; set aside.
Step 5
Using a handheld mixer or stand mixer fitted with a paddle or whisk attachment, beat the butter on high speed until creamy, about 1 minute. Add sugar and beat on high speed until creamed together, about 1 minute, scraping down the sides and the bottom of the bowl with a rubber spatula as needed.
Step 6
On high speed, beat in the eggs, one at a time, until combined, then beat in the yogurt and vanilla extract, scraping the bowl as needed.
Step 7
Pour the dry cake flour mixture into the wet ingredients. Turn the mixer to low speed and carefully pour in the milk. Beat on low speed just until all the ingredients are combined. Do not overmix. You may need to whisk it all by hand to make sure there are no lumps at the bottom of the bowl. The batter will be slightly thick.
Step 8
Remove the pan from the refrigerator. Pour and spread the cake batter evenly over the topping.
Step 9
Bake for 40 to 55 minutes. The cake is done when a toothpick inserted into the center comes out mostly clean. (A couple moist crumbs are OK.)
Step 10
Remove cake from the oven and cool on a wire rack for 20 minutes. Run a knife along the edge to loosen, then invert the cake onto a plate. (Take care, as the pan may still be hot.) Serve warm or at room temperature.

Ratings

4 out of 5

654 user ratings

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Comments

Dan Findlay3 years ago

Maraschino cherries are traditional, but can be replaced with pecan halves and/or pitted prunes, placed best side down in the holes and gaps of the pineapple. And I am willing to bet that Millie Peartree uses buttermilk, as I do, added alternately with the dry ingredients. The Greek yogurt thinned with milk seems like unnecessary, trendy fussiness.

brutallyfrank3 years ago

Yes you can. I always make it with fresh pineapple and Amarena cherries. So much better than canned pineapple and those horrible tasting, garishly red, maraschino cherries.

Bea Seeking2 years ago

Let's not yuck other peoples' yum, shall we? Maraschino cherries are traditional, almond flavored, and the color of fun.

Digger3 weeks ago

Cake wasn’t as moist as I expected and the taste of pineapple wasn’t strong enough. It tasted more sweet than distinctly pineapple.

JJ3 weeks ago

For Adults Only (bet that got your attention!). I would not ordinarily make such a cloyingly sweet dessert. But I wanted to honor a request from a special friend. So I made the following modifications. I used Woodland Reserve bourbon-soaked cherries that I bought at Williams-Sonoma. Anywhere that the recipe called for the addition of vanilla, I used bourbon instead. Used 1/3 less sugar in cake. Served with whipped cream where I added just a titch of syrup from the bourbon-soaked cherries. Obviously this was a sophisticated take on a classic dessert made exclusively for adults who inhaled the entire cake. Would definitely make again with these modifications. After all, what isn’t improved with a little bit of bourbon?! :)

Tim2 months ago

Many years ago I made pineapple upside down cake with a recipe that instructed me to add meringue at the very end to make the cake fluffy and airy. You fold it in by hand to the dry ingredients that have the other liquid ingredients added already. It was the best I've ever had, but I lost the recipe. The cake was amazingly spongy.

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