Pineapple Upside Down Cake with Cake Mix
Have you ever craved a classic dessert that’s both nostalgic and ridiculously easy to make? Well, let me introduce you to one of my favorite desserts—Pineapple Upside Down Cake with Cake Mix. It’s sweet, caramelized, and bursting with fruity goodness. The best part? You don’t have to be a professional baker to pull this off! The proof: I learned to bake this cake at school when I was around 14-15 years old! With a boxed cake mix and a few simple ingredients, you can whip up this show-stopping cake in no time.
Since my schooldays, I’ve experimented with mini pineapple upside-down cakes, vegan versions, and even gluten-free adaptations. So, I’m happy to share with you this great recipe and all the delicious ways you can make it your own!
The Origin and Tradition of Pineapple Upside Down Cake
This classic dessert has an interesting history. Before the invention of ovens with temperature control, people cooked cake recipes in cast-iron skillets over medium heat. They would place fruit (often fresh pineapple or crushed pineapple) at the bottom of the pan, pour the cake batter over it, and let the heat do the rest. The tradition of pineapple rings and maraschino cherries took off in the 1920s when canned fruit became widely available. Ever since then, this cake has been a time of year favorite for family gatherings and celebrations.
Ingredients for Pineapple Upside Down Cake with Cake Mix
For the Topping:
- 1/2 cup butter (softened butter or unsalted butter)
- 1 cup brown sugar mix
- 1 can pineapple slices or fresh pineapple (reserve 1/2 cup pineapple juice)
- 12 maraschino cherries
- 1/2 cup pecan halves (optional)
For the Cake:
- 1 box yellow cake mix
- 3 eggs (or egg yolks for richness)
- 1/2 cup vegetable oil
- 1 cup pineapple juice
- 1 teaspoon vanilla extract
- 1/2 teaspoon salt
Step-by-Step Instructions for Pineapple Upside Down Cake with Cake Mix
1. Prepare the Pan
- Heat oven to 350°F.
- Grease a cake pan with non-stick cooking spray.
2. Make the Topping
- In a small saucepan, melt the butter over medium heat.
- Stir in the brown sugar mix until it forms a caramel sauce.
- Pour the mixture into the bottom of the pan and arrange the pineapple rings and maraschino cherries.

3. Prepare the Cake Batter
- In a large bowl, combine dry ingredients: yellow cake mix, teaspoon salt.
- In a separate bowl, whisk together wet ingredients: eggs, vegetable oil, pineapple juice, and vanilla extract.
- Using an electric mixer on low speed, slowly add the wet ingredients to the dry ingredients.
- Beat at medium speed until well combined.
4. Assemble and Bake
- Carefully pour the batter over the pineapple topping.
- Bake for 35-40 minutes or until a toothpick inserted in the center of the cake comes out clean.
- Let cool for 10 minutes, then flip onto a large plate.
Mini Pineapple Upside Down Cakes with Cake Mix
Mini Pineapple Upside Down Cakes with Cake Mix are the perfect bite-sized twist on the classic dessert! They’re just as delicious, featuring a caramelized pineapple topping with a soft, moist cake base, but made in individual portions using a muffin tin. Simply place a pineapple ring and a maraschino cherry at the bottom of each cup, spoon in the buttery brown sugar mixture, and top with cake batter. Bake until golden and fluffy, then flip for a stunning, fruit-topped treat. These mini cakes are great for parties and picnics, easy to serve, and bring all the nostalgic flavors in a fun, portable size!

How to Make Mini Pineapple Cakes
- Place a pineapple ring, a maraschino cherry at the centre, and a spoonful of brown sugar butter mixture at the bottom of each muffin tin.
- Follow the same steps as above but divide the batter evenly into the muffin cups.
- Bake at 350°F for 15-20 minutes.
- Cool on a wire rack before removing from the muffin pan.
Vegan and Gluten-Free Versions
Vegan Pineapple Upside Down Cake
- Swap eggs for flax eggs.
- Use dairy-free butter.
- Choose a vegan boxed cake mix.
Gluten-Free Pineapple Upside Down Cake
- Use gluten-free yellow cake mix.
- Make sure the canned pineapple and maraschino cherries are gluten-free.
Toppings and Add-Ons
- Whipped cream
- Caramel sauce
- Crushed pineapple
- Pineapple tidbits
- Vanilla ice cream
Pro Tip
- You can replace the caramel sauce with maple syrup or even honey!
Tips for Success
- Always use room temperature ingredients.
- Store leftovers in an airtight container.
Serving Suggestions
- Serve warm with whipped cream.
- Pair with vanilla ice cream.
Nutritional Content (Per Serving)
Nutrient | Amount |
Calories | 290 |
Carbs | 40g |
Sugar | 27g |
Fat | 12g |
Protein | 3g |
Daily Value % | Varies |
Conclusion
Pineapple Upside Down Cake with Cake Mix is a classic dessert that’s easy to make and always a crowd-pleaser. Whether you stick to the original recipe, try mini pineapple cakes, or go gluten-free, there’s a version for everyone. So grab your oven mitts and start baking—your taste buds will thank you!
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FAQs
1. Can I use fresh pineapple instead of canned?
Yes! Just slice the peeled pineapple (same thickness as canned ones). You can cook the fresh pineapple slices with some sugar and water to remove the acidity. Then drain the slices and proceed like for the canned ones.
2. How do I store leftovers?
Keep in an airtight container in the fridge for up to 3 days.
3. Can I freeze Pineapple Upside Down Cake with Cake Mix?
Yes, wrap in plastic wrap and freeze for up to 2 months.
4. Why did my cake stick to the pan?
Make sure to grease the bottom of the pan well and let it cool before flipping.
5. Can I make this Pineapple Upside Down Cake without a boxed cake mix?
Absolutely! If you want to skip the boxed cake mix, you can create a homemade mix with the following:
- 2 1/4 cups all-purpose flour
- 1 1/2 cups granulated sugar
- 3 1/2 teaspoons baking powder
- 1/2 teaspoon salt
Mix these dry ingredients together, and then proceed with the rest of the recipe as directed. You’ll still use the eggs, oil, pineapple juice, and vanilla from the original cake recipe.
Printable Recipe Card

Pineapple Upside Down Cake with Cake Mix
Equipment
- 9-inch round cake pan (or a 9×13-inch baking dish)
- Mixing bowls (one large, one medium)
- Electric mixer (or whisk)
- Spatula
- Measuring Cups and Spoons
- Small saucepan (for melting butter and sugar)
- Cooling rack
- Toothpick (for testing doneness)
- Knife (if using fresh pineapple)
- Oven mitts (for safe handling)
Ingredients
For the Topping:
- 1/2 cup butter softened butter or unsalted butter
- 1 cup brown sugar mix
- 1 can pineapple slices or fresh pineapple reserve 1/2 cup pineapple juice
- 12 maraschino cherries
- 1/2 cup pecan halves optional
For the Cake:
- 1 box yellow cake mix
- 3 eggs or egg yolks for richness
- 1/2 cup vegetable oil
- 1 cup pineapple juice
- 1 teaspoon vanilla extract
- 1/2 teaspoon salt
Instructions
Prepare the Pan
- Heat oven to 350°F.
- Grease a cake pan with non-stick cooking spray.
Make the Topping
- In a small saucepan, melt the butter over medium heat.
- Stir in the brown sugar mix until it forms a caramel sauce.
- Pour the mixture into the bottom of the pan and arrange the pineapple rings and maraschino cherries.
Prepare the Cake Batter
- In a large bowl, combine dry ingredients: yellow cake mix, teaspoon salt.
- In a separate bowl, whisk together wet ingredients: eggs, vegetable oil, pineapple juice, and vanilla extract.
- Using an electric mixer on low speed, slowly add the wet ingredients to the dry ingredients.
- Beat at medium speed until well combined.
Assemble and Bake
- Carefully pour the batter over the pineapple topping.
- Bake for 35-40 minutes or until a toothpick inserted in the center of the cake comes out clean.
- Let cool for 10 minutes, then flip onto a large plate.
Notes
- Place a pineapple ring, a maraschino cherry at the centre, and a spoonful of brown sugar butter mixture at the bottom of each muffin tin.
- Follow the same steps as above but divide the batter evenly into the muffin cups.
- Bake at 350°F for 15-20 minutes.
- Cool on a wire rack before removing from the muffin pan.
- Swap eggs for flax eggs.
- Use dairy-free butter.
- Choose a vegan boxed cake mix.
- Use gluten-free yellow cake mix.
- Make sure the canned pineapple and maraschino cherries are gluten-free.
- Whipped cream
- Caramel sauce
- Crushed pineapple
- Pineapple tidbits
- Vanilla ice cream
- You can replace the caramel sauce with maple syrup or even honey!
- Always use room temperature ingredients.
- Store leftovers in an airtight container.
- Serve warm with whipped cream.
- Pair with vanilla ice cream.