
Mastering tiny pineapple upside-down cakes comes down to capturing all the flavors of the classic dessert while getting maximum caramelization in each little serving. These cute personal-sized treats display shiny pineapple circles, each topped with a bright red maraschino cherry, all tucked into a buttery caramel layer over fluffy vanilla cake. The individual size means everyone gets the perfect mix of gooey topping and soft cake, and this tested formula guarantees they'll turn out great every single time.
I've watched these mini cakes vanish minutes after serving them at so many family get-togethers. The way butter and brown sugar turn into that rich golden caramel while baking, soaking the pineapple with sweet warmth, makes an smell that pulls everyone into the kitchen. Having individual portions also means no mess when serving, which works great for casual hangouts or fancy dinner parties.
Must-Have Ingredients
- All-purpose flour: Gives just the right framework while keeping things tender - grab unbleached for better taste and consistent protein levels.
- Cornstarch: The secret to getting that soft, melty texture that makes these cakes stand out.
- Brown sugar: Go for dark brown to get deep, rich flavor in the topping, though light brown works fine too.
- Pineapple rings: Fresh brings bright tang, but canned ones give you the same thickness for more even baking.
- Maraschino cherries: Bring that sweet-sour kick and old-school charm.
- Rum or vanilla extract: Boosts those caramel notes and adds more flavor depth.
- Pineapple juice: Using what comes in the can cuts waste and pumps up the tropical taste in your cake.
Putting Together Your Mini Treats
- Get Started:
- Put your oven rack right in the middle and heat to 350°F (175°C), taking your time so it warms up all the way through.
- Fix Up Your Tin:
- Smear soft butter all over your jumbo muffin pan, making sure to get into all the nooks and edges.
- Make The Base:
- Mix melted butter with brown sugar until it looks like damp sand, then split it evenly into each cup.
- Set The Fruit:
- Place each pineapple ring right in the middle, pushing down gently into the sugar mix before adding cherries in the centers.
- Whip Up The Batter:
- Start by beating room temp butter until it's airy and light, which takes about three minutes flat.
- Mix It Right:
- Add eggs one by one, waiting until each one completely mixes in before adding another.
- Finish It Off:
- Switch between adding dry stuff and pineapple juice three times, stirring just enough to mix everything together.

The careful mix of ingredients in this recipe always brings back memories of my grandma's baking wisdom. She always told me to use eggs straight from the counter, not the fridge. After years of baking, I now get why - they make a smoother, fluffier batter that bakes into perfectly soft cakes.
Tasty Serving Ideas
Make these little cakes even better by warming them slightly and adding a scoop of homemade vanilla bean ice cream on top. They're great for brunch too, paired with fresh coffee with a hint of spice. For parties, try arranging them on different-sized cake stands, surrounded by fresh tropical fruit and pretty edible flowers. You can also drizzle them with rum-caramel sauce or serve with lightly sweetened whipped cream that's got vanilla mixed in.
Fun Twists To Try
Play around with different fruits like swapping pineapple for peach slices in summer or apple rings in fall. You can toss in warm spices such as cardamom or ginger to change up the cake flavor. If you've got dietary needs, swap in gluten-free flour mix with a bit of xanthan gum, or try coconut sugar for a less processed option. Adding crunchy toasted macadamia nuts to the topping brings extra texture and tropical flavor.
Storage Tricks
Keep these little gems in a sealed container with wax paper between layers so they don't stick together. They'll stay fresh on your counter for two days or up to five days in your fridge. When you want to warm them up, wrap each cake in foil and heat in a 300°F oven for 10 minutes, or pop in the microwave for 20 seconds covered with a damp paper towel.

After baking batch after batch over the years to get this recipe just right, I've found these mini pineapple upside-down cakes hit the sweet spot between old-fashioned comfort and modern convenience. The way the pineapple gets all caramelized with the brown sugar making that sticky-sweet top layer, while the cake underneath stays super moist, is what makes them so special. Whenever I bring these to gatherings, they bring back memories of family dinners while creating new ones with their perfect single servings and reliable results.
Frequently Asked Questions
- → Can I skip the rum in this recipe?
- Sure thing, just use vanilla extract instead of rum for both the cake and the topping.
- → What's the point of adding cornstarch?
- Cornstarch makes your cake softer and fluffier when you bite into it.
- → Will standard muffin tins work for this?
- You'll need to cook them for less time if using standard tins since they're meant for jumbo ones.
- → Why wait 5 minutes before turning them over?
- The short cooling lets the caramel thicken a bit but stays warm enough to come out cleanly.
- → Can I make these the day before?
- They taste best fresh but will keep in your fridge for up to 3 days.