Pineapple Upside Down Cake


I’m happy to inform you all that as I enter this 25th year of life my taste buds are definitely maturing. Jeff likes to tease me by saying that I’m not a real adult, since my frontal lobe hasn’t fully developed yet. I’m not sure how true that is, but he also insists that it happens when you turn 26 (insert major side-eye).  I like to think that I’m a grown woman and my mature palate is a testament to that. Just a few years ago (read: months), you couldn’t get me to eat cooked fruit.  I’m not the biggest fan of fruits *gasp*, but recently I’ve been incorporating fruit into my desserts for a more balanced meal. Like this scrumptious Nutella and Banana Brioche bread pudding, or the Apple Galette that we almost devoured in one sitting. 

Back to this super moist pineapple upside down cake. For Mother’s Day, Jeff’s mom requested a pineapple cake, something that I’ve never made before.  I have to admit, I was a little nervous about making it because no future daughter-in-law wants their future mother-in-law to think that they can’t bake.  I knew that I had to find the perfect from-scratch recipe for this, so I set off to some of my favorite sites. Luckily, Sally recently posted homemade version of her family’s pineapple upside down cake recipe. And in true Sally fashion, this did not disappoint. It’s buttery, brown sugar-y, and the cake is super moist, just they way I like it. Plus, it’s healthy seeing as it has both pineapples and cherries, right?! Right!

Here are the four most important ingredients, in my opinion – butter, brown sugar, pineapples, and cherries.  Now, if you’re feeling adventurous, feel free to get a fresh, ripe pineapple and slice that baby up. I wasn’t feeling too frisky, so I used canned pineapples.  

Once you’ve gotten your ingredients together, pour the melted butter into a 9×2″ cake pan and sprinkle the brown sugar on top. Then, add the pineapple.  I tried to fit as many slices as possible in the pan and ended up using seven slices.  Once the pineapple slices are swimming in the butter/brown sugar mix, drop in the cherries.  As you can see, I tried to fill in all the spots with cherries.  Once the cake is finished baking, you’ll invert the cake and this pretty little arrangement will be the top. 

Next, whisk all of the dry ingredients together in a medium bowl and set aside.  Then, in a large microwave-safe bowl, add the butter and …. melt.  Whisk in the sugars until the mixture is gritty and then add the remaining wet ingredients. 

Put away your stand mixer, you’re going to whisk this cake the old-fashioned way – by hand. I sure that our cake-baking ancestors are beaming down with pride.  You’ll have a few little lumps, and that’s OK.  You don’t want to over-mix the batter, which causes gluten to be released, creating a really tough cake, which is the complete opposite of what this melt-in-your-mouth was created to be. 

Pour the batter into the pan and make for 20 minutes at 350F.  When the 20 minutes are up, over with foil for the remaining 20 minutes so that the cake doesn’t get too brown. 

Once the cake is baked and cooled, invert it onto your prettiest tray and serve!

Pineapple Upside-Down Cake

Recipe Adapted from Sally’s Baking Addiction


For the Topping

  • 1/4 cup unsalted butter, melted
  • 1/2 cup light brown sugar
  • sliced pineapple (fresh or canned)
  • ~20 maraschino cherries

For the Cake

  • 1 and 2/3 cup all purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter, melted
  • 3/4 cup light brown sugar
  • 1/4 cup granulated sugar
  • 1 large egg, room temperature
  • 1/4 cup sour cream
  • 1/2 cup buttermilk
  • 1/4 cup pineapple juice
  • 1 tablespoon vanilla extract


  1. Preheat the oven to 350F degrees.
  2. Pour 1/4 cup of melted butter into a 9×2″ round cake an.  
  3. Sprinkle with 1/2 cup of brown sugar. Add the pineapple slices and place cherries around and between the pineapple 
  4. In a medium bowl, whisk together flour, baking powder, baking soda, and salt. Place to the side
  5. In a large microwave-safe bowl, melt the butter in the microwave. Add the sugars and whisk until thoroughly so that there are no lumps but the mixture is gritty. 
  6. Whisk in egg, sour cream, pineapple juice, and vanilla until well combined. 
  7. Slowly mix in the dry ingredients until no lumps remain – the batter will be thick. 
  8. Pour the batter into the pan and bake for 20 minutes. Then, cover loosely with aluminum foil and bake for another 20-25 minutes or until a toothpick inserted in the center of the cake comes out clean.  
  9. Cool for about 10 minutes and then invert the cake onto a serving plate.

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