Easy Upside Down Pineapple Cupcakes
These Mini Upside Down Pineapple Cupcakes are like little bites of sunshine—sweet pineapple rings, juicy maraschino cherries, and a buttery brown sugar topping all nestled under tender homemade cake. Made in a jumbo muffin tin, they’re the perfect size for sharing with the hubby, neighbors, or keeping a few just for us here on the ranch.
These Mini Upside Down Pineapple Cupcakes are really just adorable little pineapple upside-down cakes baked in a jumbo muffin tin. Inspired by my mama’s classic cast-iron skillet version, this smaller-batch twist lets us enjoy that old-fashioned, from-scratch pineapple upside-down cake flavor without a big pan of leftovers. Mama always made hers in that trusty skillet from scratch when we were kids, but after we grew up and left home, she switched to a cake mix for ease. I totally understand—cooking for just the two of us changes things! These sweet little cupcakes bring back all those wonderful memories with every buttery, pineapple-and-cherry bite. Simple, nostalgic, and downright delicious!
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Just look at that perfect bite! Fork-tender yellow cake soaked with sweet pineapple juices, a glossy caramelized edge, and that bright maraschino cherry on top—pure old-fashioned pineapple upside-down cake happiness in every single bite. These mini versions are dangerously easy to pop in your mouth, and one taste will take you straight back to Mama’s kitchen.
Mini Upside Down Pineapple Cake Recipe:
Topping Ingredients:
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- 2- 2o oz. cans pineapple slices
- 1 jar of maraschino cherries
- 2/3 cup of brown sugar
- 4 tbsp butter, melted
Cake batter Ingredients:
- 2 ½ cups of All purpose flour
- 1 ⅓ cups white sugar
- 2 & 1/2 tsp baking powder
- ¼ tsp salt
- ¾ cup butter, softened
- 1 tsp vanilla extract
- 3 eggs
- 1 ¼ cups milk
Special Equipment Needed:
- 2 Jumbo Muffin Tins
- Mixing Bowls
- Cooling Rack or Parchment Paper
🥣 Recipe Tips
- Don’t skip the generous spray! Be sure to generously coat your jumbo muffin tins with non-stick cooking spray. This helps the brown sugar-butter topping release cleanly when you flip them out.
- Flip while they’re still warm. After baking, let the cupcakes cool in the pan for just 5-10 minutes, then immediately invert onto a baking sheet or parchment paper. This keeps the gooey pineapple topping intact and looking beautiful.
- Make them ahead! These mini pineapple upside-down cakes store beautifully. Cover and refrigerate for up to 3 days. Bring them to room temperature or gently warm in the microwave before serving for that fresh-baked taste.
How to Make these Pineapple Upside down cupcakes
- Begin by mixing together the brown sugar and melted butter, then spoon it into the bottom of each jumbo muffin cup.
- Next, place a pineapple ring on top of the sugar mixture and put a maraschino cherry in the center of each ring.
- Mix up the cake batter and gently pour it over the pineapple rings, filling each cup about ¾ full.
- Bake in a preheated 350°F oven for 18-22 minutes, until golden and a toothpick comes out clean.
- Let them cool in the pan for just 5-10 minutes, then immediately invert onto a baking sheet or parchment paper.
These Mini Upside Down Pineapple Cupcakes are pure comfort in every bite—sweet, nostalgic, and just the right size for our ranch kitchen. Whether you’re sharing them with the hubby, the neighbors, or keeping a few for a quiet treat with coffee, they’re sure to bring smiles all around.
If you try them, I’d love to hear how they turned out in the comments below! Don’t forget to pin this recipe for later and subscribe to the newsletter so you never miss a new favorite from My Turn For Us.
Happy baking, friends — from our ranch to yours!
Other Cupcake Recipes:
🥣 Recipe
Equipment
Ingredients
Topping-
- 2 20 ounce cans pineapple slices
- 1 jar maraschino cherries
- ⅔ cup brown sugar
- 4 Tablespoon butter melted
Cake Mix-
- 2 ½ cups all-purpose flour
- 1 ⅓ cups white sugar
- 2 ½ teaspoon baking powder
- ¼ teaspoon salt
- ¾ cup butter softened
- 1 teaspoon vanilla extract
- 3 eggs
- 1 ¼ cups milk
Instructions
- Begin by mixing together the brown sugar and melted butter, then spoon it into the bottom of each jumbo muffin cup.
- Next, place a pineapple ring on top of the sugar mixture and put a maraschino cherry in the center of each ring.
- Mix up the cake batter and gently pour it over the pineapple rings, filling each cup about ¾ full.
- Bake in a preheated 350°F oven for 18-22 minutes, until golden and a toothpick comes out clean.Let them cool in the pan for just 5-10 minutes, then immediately invert onto a baking sheet or parchment paper.
Nutrition
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Great idea. So easy. However I used a cake mix. Worked great. Hubby loves pineapple up side down cakes and these are just the right size for individual servings.
Awe thanks. Clever tip about using a cake mix.
Do I need to change the recipe for high altitude cooking? If so, what do I need to add and how much or is going time longer? Thanks
Honestly I don’t know. I have never lived at high altitudes so that is not something I’m qualified to answer. I’m so sorry and hopefully someone else can help you.
I made half the recipe and they turned out so moist. Also used 2percent milk and pineapple in it’s own juice. Next time I will make the full recipe and use pineapple in syrup for more sweetness.
Oh yum! Thats a great idea. So happy you were pleased with them.
Should I refrigerate if there for the next day or leave out
Yes, these need to be covered and stored in the refrigerator