Skillet pineapple upside down cake from scratch

I grew up on a farm and learned to cook from scratch. By age 9 I could follow a recipe.So I have been cookng for a lot of years now. Besides cooking I enjoy bible study, church, crafts, collecting rings and Christmas ornaments, reading, collecting angels and visiting with friends via E mail. Have been married for over 30years and have four children, two of which are handicapped. The kids are all grown now and I am getting use to cooking smaller portions. Recently found out my husband has non-hodgkins-lymphomia. He will start treatment soon. Learning more about healthy eating and healthy cooking.

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Growing up, my favorite dessert that my mom would make is pineapple upside-down cake. It's a fun retro dessert that still definitely holds up, and is always a treat when I have some. As I got older and got more into baking, I started making a lot myself. I typically used to make it using a cake mix as the base, which is easy and always comes out great. But this from-scratch cast-iron skillet version is so easy and even more delicious!

I decided to make this cake because my friend Jackie was having a birthday this week and specifically requested pineapple upside-down cake! It's one of my favorite cakes to make, so it was definitely a no-brainer!

Why should I use a cast-iron skillet?

The method of making pineapple upside-down cake involves melting butter in the bottom of the pan, adding pineapples, brown sugar, and cherries, and then pouring the batter on top. So the caramelized pineapples and cherries become the topping, and gives the cake a buttery sweet richness. Using a well-seasoned cast-iron skillet makes it easier to melt the butter, and helps to caramelize the pineapple topping even more to take this classic cake to the next level!

That said, this cake can definitely be made in a 9-inch cake pan -- just watch the cake closely near the end of the baking time. If you do make it in a regular cake pan, let me know how it works out!

Pineapple upside-down cake step-by-step

It couldn't be easier to make this delicious cake! To start with, the super-simple batter is similar to my banana cake -- no creaming butter, and no mixer required! Once you've whipped up the batter, you'll melt butter in your skillet, and then sprinkle in your brown sugar. This will help caramelize the topping on your cake.

Then, place the cherry halves, cut side up. Ordinarily you would arrange them evenly across the cake, but I placed mine in a "J" in honor of my friend Jackie's birthday. Feel free to get creative! Once you have the cherries down, gently spoon the drained pineapple over the top.

You'll notice this recipe calls for crushed pineapple, whereas most pineapple upside-down cake recipes call for sliced pineapple rings. This is just my personal preference -- I find that crushed pineapple makes the cake easier to slice, and gets more pineapple flavor more evenly all over the cake! But it's up to you -- the method is the same whether you use crushed or sliced pineapple. If you do end up using sliced pineapple, then just put your cherry halves in the center of each slice!

In any case the final step is to just pour the cake batter over the pineapple in the skillet, and bake!

Pineapple upside down cake is wayyy too easy for how delicious it is. If you have made it this far in life without trying it, now's your chance! Plus, it calls for canned pineapple and cherries, so it's doable even if you (like me) are having a hard time getting fresh ingredients right now. Definitely give it a try and let me know what you think!

And if you like pineapple, I definitely recommend my pineapple pecan cheesecake crumb bars! They were the winning dessert in my family bake-off last year, and I can't wait to make them again!

Prep Time: 10 minutes

Cook Time: 35 minutes

Total Time: 45 minutes

Servings: 8 slices

For the topping:

• 6 tablespoon salted butter
• ⅔ cup light brown sugar
• 20 oz can crushed pineapple - drained and ⅓ cup juice reserved
• 10 maraschino cherries - cut in half

For the cake:

• ⅔ cup granulated sugar
• 2 large eggs - room temperature
• 1 teaspoon pure vanilla extract
• ⅓ cup vegetable oil
• ½ cup whole milk - (you can substitute lowfat milk or buttermilk, if desired)
• ⅓ cup pineapple juice - reserved from can
• 1 ½ cups all-purpose flour - (190g)
• 1 ½ teaspoons baking powder
• ¼ teaspoon salt

• Preheat oven to 350°F and spray an 8 or 10-inch cast iron skillet with cooking spray. (You can also use a 9-inch round cake pan -- see note)

• On the stovetop, melt butter on medium heat.

• Sprinkle brown sugar evenly over butter in pan. Add cherry halves evenly to brown sugar layer, cut side down.

• Spoon crushed pineapple over cherries and pat with the back of a spoon to distribute evenly. Set aside.

• In a large bowl or stand mixer, beat sugar, eggs, & vanilla for one minute.

• Stir in oil, buttermilk, and juice and mix well.

• Add flour, baking powder, and salt and mix with a spoon until just combined.

• Pour into pan and bake for about 30-35 minutes or until a toothpick inserted into the center of the cake comes out clean.

• Allow to cool in the pan for at least 10 minutes, then carefully invert onto a cake plate. If any of the pineapple sticks to the pan, just scrape it off and gently add to the top of the cake.

I used a Lodge 10.25" skillet for this recipe, which was a good size -- the cake, when baked, rose to the edge of the skillet.  You can also use an 8- or 9-inch cake pan, although I haven't tested that option.  Let me know your results if you try the cake that way!

Nutrition Disclaimer

Tags: birthday, birthday cake, brown sugar, cast-iron skillet, cherries, easy, pineapple, pineapple upside-down cake, single-layer cake, skillet, upside-down cake

I can't wait to see (and share) your results! Follow me on Instagram at @chenee_today and tag #cheneetoday!

Last Updated on October 27, 2021 by Chenée Lewis

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