Pineapple Upside-Down Cake

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(664)
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
Nutritional analysis per serving (10 servings)

425 calories; 16 grams fat; 9 grams saturated fat; 0 grams trans fat; 4 grams monounsaturated fat; 1 gram polyunsaturated fat; 67 grams carbohydrates; 1 gram dietary fiber; 45 grams sugars; 5 grams protein; 318 milligrams sodium

Note: The information shown is Edamam’s estimate based on available ingredients and preparation. It should not be considered a substitute for a professional nutritionist’s advice.

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Preparation

  1. Step 1

    Heat oven to 350 degrees.

  2. 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.

  3. 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.

  4. Step 4

    Prepare the cake: In a medium bowl, whisk together the cake flour, baking powder, baking soda and salt; set aside.

  5. 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.

  6. 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.

  7. 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.

  8. Step 8

    Remove the pan from the refrigerator. Pour and spread the cake batter evenly over the topping.

  9. 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.)

  10. 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.

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Ratings

4 out of 5
664 user ratings
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Comments

Dan Findlay

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.

Bea Seeking

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

brutallyfrank

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.

Kimberly Kohler

I invested in a large container of dry buttermilk, which gives me a leg up on making anything that requires buttermilk when we're out of the liquid version. It's easy and delicious!

Shannon

I made this cake the night before - line the pan with parchment paper before putting in the topping. Bake as directed. Let it cool all the way in the pan, then refrigerate. At time of serving, heat in a 300 degree oven for 5-10 minutes. Loosen the cake from the pan with a butter knife, then flip. Easy! I found a lot of misleading info on the internet about how a pineapple upside down cake always needs to be made and served on the same day so wanted to share.

Digger

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

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Credits

By Millie Peartree

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