The Best Pineapple Upside-Down Cake

My 7-year old had never had pineapple upside-down cake and she loves pineapple.

Whoa. How did that happen?

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

So I decided to get busy. It turned out to be the best pineapple upside-down cake I’ve ever had, and one of the best cakes I’ve ever put to my lips.

I think it would be a perfect cake for Easter, Mother’s Day, baby and bridal showers, brunch, or anytime you want a cheery, sunny, happy cake.

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

It’s an easy cake to make, and you don’t even a mixer. For the cake base, I adapted my favorite buttermilk coffee cake that I’ve used for so many cakes including Blueberry Muffin and Buttermilk Pancakes CakeCranberry White Chocolate Chip Bliss CakePeaches and Cream Fluffy Muffin CakeCream Cheese-Swirled Cherry and Mixed Berries Cake, and more.

I love this cake base because it’s fast and easy to make, and the cakes always turn out supremely moist, springy, and fluffy thanks to buttermilk, sour cream, and oil. That trifecta of moisturizing and tenderizing ingredients makes it impossible to have a dry cake.

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

Not to mention, the buttery, brown sugary pineapple juice that seeps down into the cake from the slices on top make the cake so soft, moist, and buttery that it just melts in your mouth.

I used one 20-ounce can pineapple slices. I kept one slice whole for the center of the cake, and then fanned 12 halves around it. My pet peeve about most pineapple upside-down cakes is that there’s not enough pineapple if you keep the rings whole and intact. The focus of a pineapple upside-down cake should be on the pineapple, so I tried to maximize the pineapple coverage on top by using a fanning technique.

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

I used the remaining 3 slices (6 halves) to line the sides of the pan.

Nobody likes bald sides.

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

After getting the pineapple and cherries in the pan, whisk together the cake batter and turn it out into the pan. I filled my 9-inch round cake pan about 3/4-inch full  with batter.

Although the cake doesn’t rise a ton, it’s still a cake and rises some, so don’t exceed about 3/4-full, the same idea as when filling a muffin tin. Discard the last bit of batter if need be. I mention this because all cake pans, exact amount of pineapple, cherries, etc will vary slightly.

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

I made the cake before bed and let it cool overnight in the pan with a sheet of foil over it. There’s no big rush to get it out of the pan. And honestly, inverting cakes gives me sweaty palms every time and I was stalling.

But because of how buttery the topping is, the pan is so well-greased that the cake just plopped right out. Not even one slice of pineapple or cherry out of order. This is exactly how it looked after inverting.

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

The cake is soft, sweet, with almost imperceptible tang from the buttermilk that adds another layer of flavor. The pineapple slices add chewiness and texture to the otherwise falling-apart-soft crumb.

While baking, the pineapple caramelizes in a butter and brown sugar bath giving the cake it’s signature glistening top and adding so much rich, browed butter flavor to the pineapple. There’s no better way to get your Vitamin C than via pineapple baked in it’s own brown sugar-browned butter sauce.

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

The maraschino cherries add a burst of sweet flavor, and they’re so eye-catching. And my daughter loves cherries.

It feels great to make nostalgic and classic recipes and between how this cake looked and how it tasted, it just made me so happy.

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

 The Best Pineapple Upside-Down Cake - So soft, moist & really is The Best! A cheery, happy cake that's sure to put a smile on anyone's face!

Print Recipe

The Best Pineapple Upside-Down Cake

The best pineapple upside-down cake I've ever had, and one of the best cakes I've ever made. It's an easy, no-mixer cake. The cake is soft, sweet, with almost imperceptible tang from the buttermilk that adds another layer of flavor. The pineapple slices add chewiness and texture to the otherwise falling-apart-soft cake. While baking, the pineapple caramelizes in a butter and brown sugar bath giving the cake it's signature glistening top and adding so much rich, browed butter flavor to the pineapple. The maraschino cherries add a burst of sweet flavor, and they're so eye-catching. The buttery, brown sugary pineapple juice that seeps down into the cake from the slices on top make the cake so soft, moist, and buttery that it just melts in your mouth. It's a perfect cake for Easter, Mother's Day, baby and bridal showers, brunch, or anytime you want a cheery, happy cake.

Yield: one 9-inch round cake, 8 to 10 servings

Prep Time: 15 minutes

Cook Time: about 40 minutes

Total Time: about 90 minutes, for cooling

Ingredients:

1/2 cup unsalted butter
3/4 cup light brown sugar, packed
one 20-ounce can pineapple slices
about 12 maraschino cherries
1 cup all-purpose flour
3/4 cup granulated sugar
2 teaspoons baking powder
pinch salt, optional and to taste
1 large egg
1/2 cup buttermilk (or Powdered Buttermilk, use 2 tablespoons with the dry ingredients + 1/2 cup water added with the wet)
1/3 cup sour cream, lite is okay (plain Greek yogurt may be substituted)
3 tablespoons canola or vegetable oil
2 teaspoons vanilla extract

Directions:

  1. Preheat oven to 350F.
  2. In a small,  microwave-safe bowl, melt the butter, about 1 minute on high power.
  3. Pour the butter into a 9-inch springform cake pan. Use your finger to run a bit of butter around the side of the pan so it's well-greased.
  4. Evenly sprinkle the brown sugar over the butter.
  5. Add 1 whole pineapple slice to the center of the pan.
  6. Halve the remaining slices vertically. Stagger them in a fan-like fashion going around the cake. I used 12 slices.
  7. Place the remaining slices around the sides of the cake pan with the curved side pointing down toward the bottom of the pan (see photos for reference). There will likely be bare side patches with no pineapple coverage, that's okay.
  8. Place 1 cherry in the center of the whole pineapple slice in the middle of the pan.
  9. Place 1 cherry in the center cutout of all the fanned pineapple slices; set pan aside.
  10. In a large bowl, whisk together flour, granulated sugar, baking powder, optional salt; set aside.
  11. In a separate small bowl, whisk together the next 5 wet ingredients (through vanilla).
  12. Add the wet mixture to the dry, mixing lightly with a spoon or folding with a spatula until just combined. Small lumps will be present, don't overmix or try to stir them smooth.
  13. Gently turn batter out into prepared pan, being careful to not disturb the pineapple slices on the sides or bottom. Fill pan only to about 3/4-full. If you have a little extra batter, discard it rather than overfilling your pan.
  14. Place pan on a cookie sheet (to catch anything that does overflow) and bake for about 40 minutes, or until center is set and not jiggly, and a toothpick inserted in the center comes out clean or with a few moist crumbs, but no batter. Only go down about 1-inch with the toothpick, not all the way to the bottom where you'll hit gooey pineapple juice.
  15. Place pan on a wire rack and allow cake to cool for at least 30 minutes before inverting, slicing, and serving. I allowed cake to cool overnight, covered with a sheet of foil, before inverting. Cake will keep airtight at room temperature for up to 5 days.

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284 comments

  1. I was really excited about this cake and followed every direction. It looked cooked and like your picture when I took it out of the oven. However, when I inverted my cake, it looked very uncooked. I only waited a couple hours, not sure if it would’ve looked better if I waited longer. I put it back in the pan and in the oven for 10 more minutes, but it was still a mess. What did I do wrong?

    • It sounds like the cake was underbaked if it looked underbaked to you. All ovens, pans, pineapple, climates, etc vary and sounds like your cake required a bit longer in the oven than mine did. I would try that next time if you try again. Thanks for trying the recipe.

  2. Can you only use a springform pan with this recipe? This looks great and this is my daughters favorite cake, I am wanting to make it today for her birthday tomorrow. 

    Thanks for sharing. Looking forward to hearing back from you. 

    • I have only made it with a springform pan so can only speak to the results if you use one. Being that it’s going to be a birthday cake, I suggest using a springform pan that you know works well and have used successfully in the past as some of them do unfortunately leak depending on the brand.

  3. Thank you so much. I am going to give it a try today. I appreciate you getting back to me. wish me luck! 

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