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The old-fashioned Pineapple Upside Down Cake is a simple and classic dessert that everyone loves. This recipe is an easy one courtesy of a vanilla cake mix that is jazzed up with a homemade caramel, canned pineapple rings and maraschino cherries. This cake has never been so good! Check out my other classic cake recipes here.
Pineapple Upside Down Cake Basics- What is it?
If you have never made a classic pineapple upside down cake before, it’s made up of two basic parts:
- The Pineapple Topping which is made with butter and brown sugar melted together, then topped with drained pineapple rings and maraschino cherries.
- The Cake Batter which is just a cake mix made as directed with water, oil and eggs.
Yes, I Use a Cake Mix
While I tested this recipe with my homemade vanilla cake, I much preferred it made with the cake mix. Not only was it faster process start to finish, I found the finished overall cake had a better texture. Plus those darn cake mixes tend to turn out every time! It’s a nice reliable ingredient.
Either a white, yellow or vanilla cake mix works perfectly for this recipe. I used a Betty Crocker 15.25 oz box of vanilla cake mix.
The unsung hero of this recipe are the cherries. Here are other cherry recipes you should try: Tart Cherry Pie, Cherry Almond Cookies, and Cherry Almond Chex Mix.
Ingredients Needed for Pineapple Upside Down Cake
- Salted Butter: For that rich, buttery flavor.
- Light Brown Sugar: Creates the perfect caramelized topping. Dark brown sugar will work too.
- Pineapple Rings: Sweet and juicy, they form the base of the cake. Drained and blotted dry.
- Maraschino Cherries: Adds a pop of color and fruity sweetness. If you don’t like them, omit.
- Yellow Cake Mix: Opt for Betty Crocker for consistent results.
- Large Eggs: To bind everything together.
- Pantry Staples: Water and vegetable oil, to complete the cake batter.
Variations
- Fresh Pineapple: Swap canned pineapple rings for fresh ones for a vibrant twist and extra flavor.
- Sour Cream Addition: Mix in a dollop of sour cream for extra moisture in the cake batter.
- Experiment with different fruit variations: like peaches or mangoes for a unique twist.
Two Tips Before You Begin
The intimidating part about Pineapple Upside Down Cake is flipping it upside down to serve it. The caramel, pineapple rings and cherries that you put in the bottom end up being the top of the cake and a pretty sticky concoction after baking. Here are three tips to give you the confidence to forge ahead:
- Use a cast iron pan. I used a 10-inch cast iron pan. I like using cast iron for this cake because the cake is heated more evenly. You do need to keep an eye on the edges of the cake so that they don’t get too crispy. If you don’t have cast iron, you can use a glass 9×13 pan. Just be sure to use plenty of nonstick cooking spray.
- Wait 10 minutes after baking before turning the cake out. This gives the cake enough time to settle and become a little more sturdy, plus the caramel sauce needs to tighten up a little bit so it doesn’t go running all over the serving dish. You’ll want to run a knife around the edges of the pan to make sure the cake is loosened before flipping it over.
I will say the beautiful thing about this cake is if some of the pineapple or cherries happen to stick to the cake pan, just pull them out of the pan carefully and replace back onto the cake.
How to Make Pineapple Upside Down Cake
I promise this isn’t a super hard cake to make. It comes together in about 15 minutes and is perfect at room temperature for a few days as long as it’s covered with plastic wrap. For full recipe details, including ingredient measurements, see the printable recipe card down below. Here’s step-by-step instructions for how to make it:
1. Preheat Oven + Prep Cast-Iron Skillet
Preheat oven to 350° F. You’ll need a 10″ cast-iron skillet (or 9×13 pan) for this cake.
2. Make the Pineapple-Caramel Topping
Melt butter and brown sugar together in the cast iron skillet until melted. Let it bubble and sizzle for 1 minute, then remove from heat.
3. Drain Pineapple + Add on Top of Caramel
Drain the pineapple juice and blot the pineapple slices well with paper towels. Do the same with the maraschino cherries. Place the pineapple rings into the bottom of the pan in a single layer, overtop of the caramel. Add a maraschino cherry to the center of each pineapple slice and fill in any extra spaces with remaining cherries. Set aside.
4. Make the Cake
Empty out cake mix into a large bowl. Make cake according to package directions stirring together with the wet ingredients (water, vegetable oil and eggs). Pour batter overtop pineapple and smooth the top with a rubber spatula. Bake entire cake in the preheated oven for about 40 minutes or until golden brown and toothpick comes out clean after being inserted. Baking time may vary slightly from oven to oven. Cool cake for 10 minutes before inverting.
5. Flip the Cake Upside Down + Serve
After the cake has cooled 10 minutes, loosen edges with a butter knife. Add a serving plate to the top of the cake pan, then invert (flip upside down) to remove cake from pan. If some of the pineapple or cherries happen to stick to the cake pan, just pull them out of the pan carefully and replace back onto the cake. Slice and enjoy warm or at room temperature.
Storage + Make Ahead Directions
This wonderful cake (and any cake for that matter) can keep around 3 days at room temperature as long as it is covered with plastic wrap. As the days go on, you will be able to tell that it’s getting a bit older, but a quick 10 second zap in the microwave should do the trick. I don’t recommend refrigeration for this cake because I don’t want the butter and brown sugar to recrystallize or harden in any way.
To Make Ahead: Bake the cake, let it cool completely, then store it covered at room temperature for up to 2 days.
To Freeze: Tightly wrap leftovers in plastic wrap and freeze for up to 1 month. Allow to defrost overnight.
Love Cake? Here are some Old Fashioned Favorites:
- Italian Cream Cake– a show stopping cake everyone loves! A classic cake that has been around for years.
- Red Velvet Cake– bright red, soft and moist cake with cream cheese frosting. SO good!
- Apple Cake– truly an old school, super simple recipe made in a round cake pan and topped with powdered sugar
- Coconut Cake– if you love coconut, give this amazing recipe a try! So light and coconutty!
- Cinnamon Streusel Coffee Cake– another cake mix based recipe that is a classic! A great weekday recipe.
More Tropical Treats to Try!
- Pina Colada Cookies with Rum Glaze
- Non Alcoholic Pina Coladas (Virgin)
- Fruit Pizza or Fruit Pizza Cookies
- Coconut Lime Pudding Cups
- Banana Coconut Cream Pies
- Banana Split Cake
With its delightful blend of flavors and simple preparation, this Pineapple Upside Down Cake is sure to become a favorite in your baking repertoire. Whether it’s for a special occasion or a casual sweet treat, this recipe never fails to impress. The printable recipe card is below! Have a great day, friends.
If you make this recipe, I would really appreciate it if you would give it a star rating and leave your review in the comments! If you have a picture of your finished dish, post it on Instagram using the hashtag #laurenslatest and tagging me @laurens_latest.
Pineapple Upside Down Cake
Ingredients
- 1/2 cup salted butter
- 1 1/4 cups light brown sugar
- 20 oz pineapple rings drained and blotted dry; 1 can
- maraschino cherries drained and blotted dry
- 15.25 oz yellow cake mix Betty Crocker brand preferred
- 1 cup cold water
- 1/2 cup vegetable oil
- 3 large eggs
Equipment
- 10-inch cast iron pan
Instructions
- Preheat oven to 350° F.
make the pineapple-caramel topping
- In a cast iron skillet, melt butter and sugar together. Once the brown sugar has melted into the butter and bubbled up, remove from heat.
- Arrange prepared pineapple rings to the brown sugar mixture to cover the bottom of the pan. Add in maraschino cherries to the center of each pineapple ring and set aside.
- In a large bowl, stir cake mix together with water, oil and eggs according to package directions.
- Pour batter over pineapple and cherries in pan and smooth the top.
- Bake at 350° F for 28-35 minutes or until toothpick comes out clean or with a few moist crumbs.
- Cool 10 minutes before running a knife along the edges of the skillet and flipping onto a serving platter. Slice and enjoy!
This was my 1st attempt at making pineapple upside-down cake. O.M.G. It was fantastic! I was hesitant about using my cast-iron skillet because I did not care for the taste when my mom used it to make the cake years ago.
The only addiition to the recipe was that I added about 1 tablespoon of the pineapple juice to the batter.
Definitely a chef’s kiss recipe!
I made this today using very well drained pineapple tidbits and substituted 1/2 the water for the reserved pineapple juice. Used Betty Crocker Super Moist Yellow cake mix. It was DELICIOUS!! My husband LOVES pineapple upside down cake and prefers it with tidbits. It released beautifully from the glass baking dish. I baked for 35 minutes, but next time will take the baking time down to 30 minutes as the bottom got a bit too dark. This is the best recipe! Thank you!
I have made this in the past, but always “on the fly”. Wanted to refresh my memory, so searched online. Myself, I believe I used parchment paper liner in the cake pan to have an easier time getting the cake out. I also think I just added a layer of brown sugar (no butter), and it caramelized itself as the cake baked. I also generally substitute the pineapple juice from the can for the water. it gives extra flavor to the cake. And I melt butter to use instead of vegetable oil when I use cake mixes–I just like the taste better, as some oils can leave am odd aftertaste. But thank you –you helped jog my memory. I plan to make it this week for my birthday cake! 😀