Best Skillet Pineapple Upside Down Cake

Take a trip down memory lane with this Skillet Pineapple Upside Down Cake. It's a beautiful cake that's rich, buttery, and melt in your mouth delicious. Be sure to make this classic recipe to share with your family and friends that are sure to give it rave reviews. 

If you're craving more sweet recipes made with pineapple, try making a batch of Pineapple Tarts with Puff Pastry, a Yum Yum Cake, and Hummingbird Coffee Cake. 

I cannot remember exactly when I first tried pineapple upside down cake. But I do remember that it started by combining dry pantry staples to form a yellow cake mix, before adding a few items from the refrigerator, to pour on top of a pineapple mixture that still didn't look like much to talk about.

Even when the cake comes out of the oven it's still not very impressive. But once you flip it upside down, you have a cake that's a showstopper for sure. 

Let's get started!

Why You'll Love This Recipe 

• It's a classic cake recipe that's pure nostalgia. Just thinking about buttery yellow cake topped with a decadent layer of caramelized pineapples and cherries takes me back to my grandmother's kitchen. 
• Super easy! This cake is so simple to make and although the instructions say to use an electric mixer, you can totally stir it by hand in a large mixing bowl with a wooden spoon or even a whisk. 
• The perfect skillet cake recipe that can be made in a 9-inch or 12-inch skillet. Plus it adds a nice caramelized and slightly crisp top layer that's sure to stop the show once it's inverted onto your favorite cake plate. 

Ingredients You'll Need 

1. Butter - Added to the cake batter to make the cake rich and buttery, also used to form the brown sugar mixture.  
2. Brown Sugar - I prefer to use light brown sugar because it's similar to granulated sugar, but feel free to use dark brown sugar if you would like. This ingredient gives sweetness to the pineapple layer and makes it sticky with a slight crisp. 
3. Pineapple Slices - A staple ingredient when it comes to making classic pineapple upside down cake. Layer the rings at the bottom of the cast iron skillet. Crushed pineapple can be used instead, this is actually what my mom always used. 
4. Maraschino Cherries - Added to the center of the pineapple rings to create the top of the cake. Gives the cake a pop of red color and a slightly tart flavor. If you're using crushed pineapple, then you can omit this ingredient. 
5. All-Purpose Flour - Plain all-purpose flour with no additional ingredients is needed to make the cake layer and give it a great texture. 
6. Baking Powder - Helps to make the cake light and fluffy. Be sure to check the date of the package before using it to make sure that it has not expired. 
7. Salt - When it comes to baking I like using kosher salt or baking salt to bring all of the ingredient flavors together. 
8. Granulated Sugar - Used to sweeten the cake, but not make it overly sweet. 
9. Egg - A single large egg is added to the cake batter to bind the cake together. 
10. Milk - Try to use whole milk for this one. It makes the cake slightly creamy and moist. 
11. Vanilla Extract - Gives the cake a hint of vanilla flavor. Try to use pure vanilla extract and not imitation if you can.

See the recipe card below for exact ingredient quantities and instructions.

How to Make the Best Pineapple Upside Down Cake

Begin the cake recipe by preheating the oven to 350 degrees F. Grab a 9-inch cast-iron skillet and place it on the stovetop over medium heat. Allow it to heat and add the butter until melted and foamy.

Stir in the brown sugar and pineapple juice. Continue stirring the mixture until the sugar dissolves.

Remove it from the heat and add the pineapple slices to the top. Place a maraschino cherry into the center of each pineapple ring. 

In a small bowl, whisk together the all-purpose flour, baking powder, and salt until combined. Use a stand mixer with a paddle attachment or a large bowl with a hand mixer. Add the butter, and granulated sugar, and mix until light and fluffy, about 3 minutes.

Scrape down the sides of the bowl before adding in the egg, milk, vanilla extract, and reserved juice. Add the flour mixture and mix enough to combine. 

Carefully pour the cake batter into the prepared skillet on top of the pineapple mixture, trying not to disturb the pineapple topping. Smooth out the cake mixture into an even layer.

Place into the oven and bake for about 25 to 30 minutes, until a cake tester comes out clean or with a few dry crumbs.

Carefully remove the cake from the oven and allow it to cool for 10 to 15 minutes before inverting it on a serving plate to serve. Slice and enjoy!

Recipe Tips & Tricks

• Layer as many pineapple rings into the bottom of the pan as you want. It's okay if they overlap a little bit and you can also cut them to fit. 
• Run a knife all the way along the sides of the pan to loosen the cake before turning the skillet upside down on a plate. Tap the bottom of the skillet and the cake should slide right out. 
• This cake can be made in a 9 or 12-inch ovenproof skillet, but keep in mind when making it in a 12-inch skillet, the cake layer will be wider and slightly thinner. A round baking dish or round cake pan could be used instead. 
• Allow the cake to cool in the pan for at least 10 minutes before trying to remove it from the pan. You can place the skillet on top of a wire rack to allow air to circulate underneath the bottom of the skillet. 
• Try to allow your cold ingredients to come up to room temperature, this helps them to mix so much easier.

Storage Tips 

Storage. Once the cake cools to room temperature, you can store it at room temperature for 1 to 2 days if it lasts that long. Simply place it in an airtight container, cake storage container, or wrap it tightly in plastic wrap. Cut a slice or two whenever you're ready to enjoy it. If you need more time or during warmer areas, store it in the refrigerator for up to 4 days. When you're ready to eat it again, allow it to come up to room temperature before taking a bite. 

Freezer. The fully baked cake can be stored in the freezer in a freezer-safe container or freezer bag for up to 1 month. Allow it to thaw in the refrigerator overnight. I find that this cake is best eaten shortly after it's made as freezing does change the texture a bit. 

Want More Easy Cake Recipes? Try These: 

• Classic Strawberry Shortcake Recipe 
• Yum Yum Cake 
• Homemade Sour Cream Pound Cake 
• Boston Cream Pie 
• Little Layer Chocolate Cake 
• Sun Drop Pound Cake 
• Rum Cake 

Have any comments, questions, or other delicious ways to enjoy this Pineapple Upside-Down Cake? Please share them in the comments below!

📖 Recipe