Pineapple Upside Down Cupcakes
My pineapple upside-down cupcakes feature moist vanilla cake topped with a rich caramel sauce and juicy fruit. These are so much easier to make than the cake!
I love sharing easy cupcake recipes like confetti cupcakes, Margarita Cupcakes and Nutella Cupcakes. These pineapple upside-down cupcakes are another classic favorite. My Grandma often made this dessert when I was growing up. Pineapple upside-down cake is one of those classic recipes. My Grandma made it often when I was growing up. These taste just like the cake but are quicker and easier to make.
They're also great for a crowd because everyone gets their own little dessert. We like them for birthdays, potlucks, and BBQs. For an extra special treat, serve with whipped cream or vanilla ice cream.
Why I Love This Recipe
- Easy: No worrying about flipping a whole big cake. These are easy to make and always slide right out of the pan.
- Common Ingredients: Made with pantry ingredients you likely already have on time.
- Stay Moist For Days: The brown sugar syrup and fruit make sure these never dry out.
Ingredient Notes and Shopping Tips
- Flour: Measure your flour by spooning it into a measuring cup and leveling it with a spoon. Avoid dipping your cup into the flour as you'll likely use too much, which will lead to a dense, dry cake.
- Baking Powder: Replace every 6-12 months as it does lose its potency over time.
- Butter: You want your butter to be softened but not melted. If your finger makes an indent when you press it, it is ready to use.
- Milk: Use whole milk for the moistest cake.
- Marachino Cherries: These can be tricky to find at the store. Try looking in the cocktail mixer section or near the ice cream cones.
Pineapple Rings
Be sure to drain in a strainer to remove excess moisture. Then pat dry with paper towels. I would not suggest using fresh pineapple here as it may be too juicy.
One can of pineapple rings is not enough, and two will give you leftovers. When life gives you extra pineapple, make my margaritas or Elvis cake!
❓FAQs❓
Yes, make up to one day in advance.
I suggest rings as they make the presentation prettier with the cherry in the center. However, if all you have are chunks or tidbits, they'll still taste great.
No, this is one recipe where I would avoid liners. The recipe depends on the cupcakes being flipped and released from the pan. Liners could make them stick or even crumble.
Be sure to drain and pat your pineapple dry. I also suggest using canned vs. fresh as fresh pineapple can release too much liquid.
️Krystle's Tips️
- Don't overmix your batter: This can lead to tough dense cupcakes.
- Don't Overbake: Cupcakes are done when a toothpick inserted in the center comes out with a with just a few moist crumbs. It's okay if it's not totally clean.
- Don't Overfill: Fill your cupcake pan only around ⅔ of the way full. They'll rise as they bake. You don't want them to overflow and make a mess!
Perfect Flipping Everytime
I suggest turning them upside down onto a baking sheet or wire rack around 5-10 minutes after removing them from the oven.
If they don't come out immediately, let gravity do its work. You can also try gentling and loosening with a butter knife.
More Cupcakes I Love
📖 Recipe
Easy Pineapple Upside Down Cupcakes
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Ingredients
For the Topping
- (2 ) 20 Ounce Cans Pineapple Slices
- 1 Jar Maraschino Cherries
- ⅔ Cup Brown Sugar Packed
- 4 Tablespoons Butter Melted
For the Cakes
- 2 ½ Cups All Purpose Flour
- 1 ⅓ Cup White Sugar
- 2 ½ Teaspoons Baking Powder
- ¼ Teaspoon Salt
- ¾ Cup Butter Softened
- 1 Teaspoon Vanilla
- 3 Eggs
- 1 ¼ Cups Milk
Instructions
- Preheat oven to 350 degrees F. Spray a mini Bundt pan with non stick baking spray.
- In a medium bowl, combine brown sugar and melted butter. Divide between muffin tins. Also, add one pineapple slice and one cherry to each.
- In a large bowl, combine flour, salt, and baking powder.
- In another large bowl, cream butter and sugar until light and fluffy. Add vanilla, and eggs one at a time.
- Alternate adding in flour mixture and milk until everything is just combined.
- Divide evenly between prepared pans. Bake for 18-22 minutes.
- Cool before flipping over.
Notes
-
- Flour: Measure your flour by spooning it into a measuring cup and leveling it with a spoon. Avoid dipping your cup into the flour as you'll likely use too much, which will lead to a dense, dry cake.
- Butter: You want your butter to be softened but not melted. If your finger makes an indent when you press it, it is ready to use.
- Pineapple: Be sure to drain in a strainer to remove excess moisture. Then pat dry with paper towels. I would not suggest using fresh pineapple here as it may be too juicy.
- Marachino Cherries: These can be tricky to find at the store. Try looking in the cocktail mixer section or near the ice cream cones.
- Don't overmix your batter: This can lead to tough dense cupcakes.
- Don't Overbake: Cupcakes are done when a toothpick inserted in the center comes out with a with just a few moist crumbs. It's okay if it's not totally clean.
- Don't Overfill: Fill your cupcake pan only around ⅔ of the way full. They'll rise as they bake. You don't want them to overflow and make a mess!
- Perfect Flipping: I suggest turning them upside down onto a baking sheet or wire rack around 5-10 minutes after removing them from the oven. If they don't come out immediately, let gravity do its work. You can also try gentling and loosening with a butter knife.
Nutrition
So delicious! I like the individual sized cakes so much more than slicing a whole cake. These were a hit at our block party!
This worked exactly as written, thanks!
So fun and delicious!!! My family inhaled these!!!
Will pineapple chunks work instead of the rings?
Hello fellow Krystal! I wouldn't suggest using the chunks as you won't get the same caramelized flavor or presentation as you do with the largest surface area of the ring, but you know your tastes and skills best.
How would the directions change if using "mega" muffin cups vs. standard?
Hi Janelle,
We've only tried the recipe as written. I don't want to speculate on something I haven't personally tested.
These are soooo good! I made 12 jumbo muffins and baked for 25 minutes. Thanks for the recipe, definitely a keeper!
Since no size of muffin pan was mentioned, I used a standard muffin pan and found that 1/2 of the recipe made 12 cupcakes. Which is good, because the 4 of us demolished them. So good!
Yay so glad you all enjoyed them. I'll update the recipe to make the sizing more clear.
What size pan
Hi Carole,
I just used a standard muffin/cupcake pan for these.
This is seriously the best upside down cake I've tried! Thanks for the recipe!
Mmmm.... It looks so inviting! My favorite pineapple dessert!
My kids helped me make these and not only were they so tasty, but they were super cute!
Thank you so much for this pineapple upside down cupcakes recipe! This is very easy to make and really delicious! Will surely make this again! Well done!
These Pineapple Upside Down Cupcakes are on my must-make list!
These look amazing! I will be trying them out this weekend, cannot wait!
Was at the Mexican market this morning and saw some pineapple upside down cupcakes! Thought they looked amazing but decided to not buy them but make them instead! Perfect timing with this recipe! One of my favorite cakes and I LOVE it in cupcake size! Moist, delicious, and a little bit caramelized. I'm not sure how I could possibly love this more! 🙂
Every time my daughter and I make pineapple upside down cake, we always fail, but with your recipe ours turned out perfect and so delicious! So yummy. Can’t wait to make this again!