Pineapple Upside-Down Cake

Pineapple Upside-Down Cake
Armando Rafael for The New York Times. Food Stylist: Simon Andrews.
Total Time
1½ hours
Rating
4(531)
Notes
Read community notes

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
    • cup/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.

Ratings

4 out of 5
531 user ratings
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Cooking Notes

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.

My wife put soy sauce in the unlabeled container where we usually put vanilla extract, and you probably know where this is headed - I ended up putting 1/2 tsp of soy instead of vanilla in the topping! Luckily my daughter caught the mistake before I also put the soy sauce in the cake. In the end though, I think the soy in the topping added a dash of umami and cut the sweetness in the fruit just a bit. Overall, delicious!

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.

This is an old fashioned recipe made using pantry staples. It is quick and economical. I'm sure it would be great with fresh pineapple, but in our rural stores fresh pineapples are usually very unripe and quite expensive.

This is my go-to dessert. I use a yellow cake mix, lemon or orange zest, a good brand of canned pineapple, dark brown sugar, butter, cinnamon and a few raisins. Pineapple juice (instead of water) and zest go in the batter. Over 1 1/4 sticks of butter melted in a 9x13” pan, I layer 1 1/2 C sugar, a dust of cinnamon, pineapple rings or chunks, raisins and the batter and bake as directed. The moisture and flavor improves if made a day ahead. It’s always a hit, especially with whipped cream.

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

We always cook it in a cast iron skillet, but the ones that are enamel coated are even better. Magic and oh, so good!

Hi Nancy, I have the same problem! Try this: hold down the Ctrl key (left of space bar) and press the + symbol. The screen text will increase in size.

Though Greek yogurt may be "trendy", I am much more likely to have it on hand than buttermilk. It makes a great sub for sour cream and other dairy products, plus I like to eat it!

Hi, WJ! Thank you for flagging. The headnote was incorrect: You can use the pineapple juice in place of the whole milk (not buttermilk).

This was delicious. I used a 9" cake pan as written. The cake was quite high so when I tipped it over, it rolled a bit to one side. :) Next time I think I will use a 10" cake pan to make it a bit more squat and to get more pineapple real estate on the bottom.

I haven't tried this recipe yet, but as someone who does occasionally use a box mix, my experience is that cakes from scratch are ALWAYS better! And my sisters the cake bakers would agree. It doesn't seem to complicated to me, although it may to others. Let's try it & see!

Hi! I made this today using fresh peaches in the topping. It was delicious! The cake is nice and light and the topping good, sweet but not too sweet. I added a few extra spices - ground ginger, nutmeg and cinnamon - in the topping and the cake, and used sour cream since out of yoghurt, but otherwise followed the recipe. A pleasant, relatively easy cake. Tasty! Recommend it.

Can one use fresh pineapple instead of canned? And will Amarena cherries work instead of maraschino?

If you’re going to the trouble of making your cake then for God’s sake buy a fresh pineapple. Canned is nothing like the real thing. You might need to plan ahead a few days to allow your unripe market pineapple to be ready but the result is totally worth it. Add your maraschino cherries if you wish but I prefer to leave them out. Eat it for dessert and next day for breakfast. Wonderful.

Made this for Father's Day. I found the cake to be quite dry. Bummer.

I used a little less than 1/4c Greek yogurt and substituted buttermilk instead of using whole milk. Turned out delicious.

I suggest edited step 2 to say brown sugar instead of just sugar

Well it smells really good but I lost half of the cake batter into the pan underneath. What kind of cake pan are you supposed to use to keep this all together? If I use my cast iron pan will the cake slide out nicely? Details……

This was denser and heavier than expected. It felt more like a coffee cake. Of course, it could be user error. My butter was a bit colder than it should have been when I started, and I didn’t sift the flour.

FRESH PINAPPLE ....that's how we do it in Hawaii. It's much better

Made it as written except in a 12 in. stainless steel Cuisinart skillet and using about a 1/2 jar of Luxardo maraschino cherries leftover from the Holiday cocktail season. It was exceptionally delicious with beautifully caramelized fruit and a slightly toasted edge. Because it was baked in the larger skillet the cake spread over a wider area and therefore thinner. However, my family all thought the depth of the cake was perfect and was not overdone or dry at 45 mins of baking time.

I love this cake. I didn’t have cake flour so I added cornstarch and it turned out with a moist but fluffy texture. The 2nd time I made it I increased the amount of caramel topping by 1.5, which I think made it better.

Making this in the tropics with freshly picked pineapple. The fruit was so fresh I didn’t want to spoil it with imitation vanilla (all that was available), so substituted Campari. Also substituted 1/4 cup of Cassava flour for all purpose flour which worked beautifully

This is a tasty and simple cake recipe. The pineapple adds a sweet (but not too sweet) topping, and the cake itself is light, fluffy, and moist.

Can you sub sour cream for the greek yogurt?

You can only enjoy an upside down cake made with canned pineapple, if you've never tasted it made with fresh pineapple. The difference in flavor is astounding! Now I only make the cake if I can get fresh pineapple. I also skip the ultra red dyed maraschino cherries, which don't resemble anything edible...

Bake in a cast iron skillet like my grandmother used for a cake that looked just like this picture. I miss her.

We used to make these back in the 70s using an electric frying pan, tinned pineapple & those gosh-awful maraschinos in the thick syrup that were dyed lipstick red & the consistency of plastic. The cake was standard fare at every dinner party & perfect if you lived in a dorm at uni, no oven needed. I was living in Toronto at the time, so hardly "Southern". I suspect you can still find the recipe in old Sunbeam appliance manuals.

I made this for my dad for Father's Day, as he really loves pineapple upside down cake. I followed the directions, except I don't like maraschino cherries, so substituted with dark sweet cherries. I used frozen, but canned would work fine, too. The cake was a hit with Dad, and was very tasty and moist.

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Credits

By Millie Peartree

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