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Pineapple upside-down cupcakes are one of those desserts that never go out of style. It has been showing up at family gatherings and potluck tables for generations and for good reason. These cupcakes give you all that nostalgia in individual servings, with no slicing, and a caramelized brown sugar topping that is impossible to resist.
Sometimes baking doesn’t have to be from scratch, and these pineapple upside down cupcakes are proof of that. I make them with a box of cake mix, and they are just as good as anything you would make from scratch. The trick is swapping the water for pineapple juice in the batter, which sounds small, but you can really taste it. Nobody ever knows, and nobody ever asks, because they are too busy eating them.
The real star is that caramelized brown sugar and butter topping. It bakes right into the bottom of each cup, and when you flip them out, it is just gorgeous. That is the part people talk about. Honestly, the hardest part of this whole recipe is waiting until they cool down enough so they don’t burn your mouth!
Why You’ll Love This Pineapple Upside Down Cupcake Recipe
These cupcakes have everything going for them — big flavor, easy cleanup, and a wow factor that looks like you worked much harder than you did.
- That caramelized topping is the whole show. Brown sugar and melted butter go into the bottom of each cup and bake into a sticky, golden topping that is hard to resist.
- Pineapple juice in the batter makes a real difference. Every bite has fruit flavor built right in, not just at the top.
- They are made for a crowd. 24 individual cupcakes, no slicing, no uneven pieces. Everyone just grabs one.
- Make them ahead with no stress. These hold up beautifully, so you can bake them the day before.
- They look impressive, but so easy. That glossy pineapple topping with the cherry in the center does all the work for you.
Ingredients for Pineapple Upside Down Cupcakes
- Pineapple cake mix: This is what gives the batter that extra boost of pineapple flavor. If you can’t find it, yellow cake mix works just as well.
- Pineapple juice: You’re swapping this in for the water called for on the box. It’s a small change but you can really taste the difference in every bite.
- Vegetable oil: Keeps the crumb moist and tender. Stick with a neutral oil so it doesn’t compete with the pineapple flavor.
- Eggs: Three large eggs give the batter structure and help it rise evenly.
- Butter: Melted butter goes right into the bottom of each muffin cup and teams up with the brown sugar to create that caramelized topping. Don’t skimp here, it’s the good stuff.
- Brown sugar: This is where the magic happens. As it bakes with the butter and pineapple it turns into that sticky, golden topping everyone loves.
- Crushed pineapple: Drain it really well before using and press it between a few paper towels if it still seems wet. Too much moisture and you’ll lose that caramelized topping.
- Maraschino cherries: Pat these dry before placing them in the cups. They hold more liquid than you’d think, and it can affect the topping if you skip this step.
How to Make Pineapple Upside Down Cupcakes with Cake Mix
✱ Be sure to see the recipe card below for exact ingredients and full recipe instructions!
Step 1 | Prep Your Pans
Preheat your oven to 350℉.
Spray two 12-count muffin pans generously with non-stick cooking spray. Make sure you get the sides too. A good coating makes all the difference when it’s time to flip.
Step 2 | Mix the Batter
Combine the cake mix, oil, eggs, and pineapple juice in a large bowl.
Mix on low speed until just combined, then bump it up to medium and mix for 2 minutes. Set the batter aside while you build the topping.
Step 3 | Build the Topping
Spoon 1 teaspoon of melted butter into the bottom of each muffin cup.
Add 2 teaspoons of brown sugar to each cup and spread it evenly over the butter.
Place one cherry right in the center of each cup.
Then add 1 tablespoon of well-drained crushed pineapple and gently press it down into an even layer.
Step 4 | Fill the Cups
Fill each cup with batter to about two-thirds to three-quarters full.
The batter rises as it bakes, and the topping can bubble, so leave yourself some room to avoid overflow.
Step 5 | Bake
Bake on the center rack for 20 minutes, or until a toothpick inserted into the center of the cake comes out clean. Insert the toothpick only partway down so you stay in the cake layer and don’t hit the pineapple topping underneath.
Step 6 | How to Flip Pineapple Upside Down Cupcakes
Let the cupcakes rest in the pan for about 5 to 10 minutes after pulling them from the oven. You want them cool enough to hold together, but that brown sugar topping still needs to be warm and loose so everything releases cleanly. Don’t wander off, though. Waiting too long is how you end up with stuck cupcakes and a sad topping situation!
Before you flip, lay a sheet of parchment or wax paper on your counter where you’ll be working (especially if you are using a cooling rack). That brown sugar topping can drip a little, and it makes cleanup so much easier.
If you notice any of the cake sticking to the edges, run a thin knife gently around the outside of each cupcake to loosen it up before moving on. This step may not be necessary, but it can save you a headache if things are hanging on a little.
Place a baking sheet or cooling rack on top of the pan, making sure it covers the whole thing edge to edge. Grab your oven mitts and get a good firm grip on both the pan and the baking sheet. Then flip the whole thing over in one smooth, steady move. I know it can feel a little nerve-wracking the first time, but you’ve got this!
Leave the pan sitting on top for just a few seconds, then slowly lift it straight up and off. Give the bottom of the pan a gentle tap with your hand or the back of a spoon if any cupcakes need a little encouragement. A light nudge is usually all it takes.
Check each cupcake and press any shifted pineapple topping back into place while everything is still warm. It sets right back and looks like nothing ever happened. Then let them finish cooling and get ready to serve — they never last long!
Easy Swaps and Substitutions
- Yellow cake mix: Can’t find pineapple cake mix? Yellow works just as well. You’ll still get plenty of pineapple flavor from the juice and the topping.
- Pineapple tidbits or chunks: Both work great in place of crushed pineapple. Tidbits give a slightly chunkier topping, and chunks can be cut down to fit. Just make sure to drain them really well either way.
- Dark brown sugar: If that’s what you have, go ahead and use it. It gives the topping a slightly deeper, more molasses-forward flavor, and honestly, it’s delicious.
- Coconut oil: Swap the vegetable oil for melted coconut oil if you want a little tropical twist in the batter.
- Toasted coconut: Press a little onto the topping right after flipping for extra texture and flavor. Such a fun touch if you’re serving these at a party.
- Gluten-free: Use your favorite gluten-free yellow cake mix in place of the regular cake mix. Just let the batter rest about 30 minutes before baking. Check that your baking spray, brown sugar, and maraschino cherries are all certified gluten-free as well. If you are baking for someone with celiac disease, please read every label carefully because cross-contamination can be a concern even with naturally gluten-free ingredients.
Shortcuts & Time Savers
Drain ahead: Drain the crushed pineapple the night before and store it covered in the fridge. It saves you a step on baking day and gives it extra time to drain thoroughly.
Tips for the Best Caramelized Pineapple Cupcakes
- Drain the pineapple really well. This is the most important step. Press it between paper towels if needed. Too much moisture prevents the caramelized topping from forming, and you’ll end up with a soggy layer instead of a golden, sticky one.
- Pat the cherries dry. They hold more moisture than you’d think. A quick pat with a paper towel before placing them in the cups makes a real difference in the final topping.
- Don’t use cupcake liners. The brown sugar and butter need direct contact with the metal pan to caramelize properly. Liners get in the way of that and can stick during the flip.
- Don’t overfill the cups. Two-thirds to three-quarters full is the sweet spot. The batter rises and the topping bubbles, so leaving room prevents overflow and keeps your oven clean.
- Work with confidence when you flip. One smooth, steady motion is all it takes. Hesitating mid-flip is when things go sideways.
- Have everything ready before you flip. Get your parchment paper down and your baking sheet in hand before you even pull the pans from the oven. Those 5 to 10 minutes go faster than you think.
What to Serve With Easy Pineapple Upside Down Cupcakes
A dollop of freshly whipped cream is my favorite way to serve these (or try my marshmallow whipped cream). My homemade whipped cream comes together in just a few minutes and honestly takes these over the top. A light dusting of powdered sugar right before serving is a nice touch, too, especially if you are bringing them somewhere.
For a party or potluck, these are great alongside a scoop of vanilla ice cream or a simple fruit salad.
The good news is they are delicious warm or at room temperature, so you do not have to stress about timing when you are feeding a crowd. Set them out and don’t blink, they go fast!
Storage and Make Ahead Instructions
Storage: Keep leftovers in an airtight container in the refrigerator for up to 4 days. The fruit in the topping means these should not be left out at room temperature for extended periods.
Make Ahead: These bake and flip beautifully the day before. Store them covered in the refrigerator and let them come closer to room temperature before serving, or warm them briefly in the microwave for about 15 to 20 seconds.
Freezing: Yes, these freeze well! Wrap each cupcake individually in plastic wrap and place them in a freezer-safe bag or container. They’ll keep for up to 3 months. Thaw at room temperature before serving.
Recipe FAQs
Fresh pineapple is not recommended here. It has too much moisture and contains an enzyme that can affect how the cake bakes. Canned crushed pineapple, tidbits, or chunks all work great.
No, and actually you shouldn’t. The topping needs direct contact with the metal pan to caramelize. Liners prevent that and can stick when you flip.
Absolutely. Yellow cake mix works just as well. The pineapple flavor still comes through from the juice and the topping.
Yes. Because of the fruit topping, store these in the refrigerator rather than leaving them on the counter. They’ll keep well for up to 4 days.
It happens to everyone at some point! Just scoop it up with a spoon while it’s still warm and press it right back onto the cupcake. It sets back in place perfectly, and nobody will ever know.
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Pineapple Upside Down Cupcakes
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Equipment
Ingredients
- 1 box pineapple cake mix - or yellow
- 3 large eggs
- ½ cup vegetable oil
- 1 cup pineapple juice
- 1 cup butter - melted (about 1 tsp per cup)
- 24 maraschino cherries - patted dry (1 each)
- 1½ cups brown sugar - about 2 tsp per cup
- 4 cups crushed pineapple - well-drained (about 1 TBSP per cup) – reserve the juice. You will need 2 – 20 ounce cans.
Instructions
- Preheat the oven to 350℉ degrees.
- Spray two 12 count cupcake or muffin pans with non-stick cooking spray.
- Mix cake mix, oil, eggs and pineapple juice on low speed of mixer until combined. Switch to medium speed and mix for about 2 min.
- Spoon 1 teaspoon melted butter in the bottom of each muffin cup.
- Add 2 teaspoons of brown sugar to each cup. Slightly press it down with the measuring spoon so it is evenly distributed in the bottom of each muffin cup.
- Place a cherry in the center of the brown sugar and lightly press it into the brown sugar.
- Add 1 tablespoon of the crushed pineapple to each cup and use a spoon to evenly distribute it in the bottom of each muffin cup.
- Scoop the cake batter into each muffin cup, fill about ¾ the way full.
- Bake on the center rack of the oven for 20 minutes or until a toothpick inserted in the center comes out clean. (Only push the toothpick part way into the cupcake so you don’t reach it into the pineapple mixture.)
- Remove from the oven and allow the cupcakes to cool for about 5-10 minutes.
- Place parchment or wax paper on the counter surface.
- Then use a knife to gently loosen the cupcake from the edges of the pan before inverting. Place a wire cooling rack over the cupcake tin and, carefully, using potholders, keep the cooling rack pressed securely against the tin, and invert cupcakes onto the cooling rack. Lay the cooling rack on the parchment paper (you could also use a baking sheet) Lift the tin, the cupcakes should release easily. Be sure each cupcake is right side up.
Notes
- Do not use cupcake liners. The brown sugar and butter need direct contact with the metal pan to caramelize properly.
- Drain the crushed pineapple really well before using. Press it between paper towels if it still seems wet. Too much moisture and you will lose that caramelized topping.
- Pat the maraschino cherries dry before placing them in the cups. They hold more liquid than you think.
- When testing for doneness, insert the toothpick only partway into the cupcake. You want to stay in the cake layer and not hit the pineapple topping underneath.
- Let the cupcakes rest in the pan for 5 to 10 minutes after baking before flipping them out. Too soon, and they fall apart. Too long and the topping sticks.
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