There’s something about tiny desserts that makes adults lose all self-control. Maybe it’s the nostalgia, maybe it’s the smug joy of having your own cake — no sharing required. Either way, these Mini Pineapple Upside-Down Cakes deliver all the retro charm of the classic, just shrunken into bite-sized bliss.
Golden pineapple rings melt into a glossy brown sugar caramel, cherries wink from the center like cocktail jewels, and the cake itself is soft, buttery, and just tropical enough to make you forget you’re standing barefoot in a messy kitchen.
Why You’ll Love These Mini Cakes
- Built-in portion control (until you realize three count as one).
- Retro dessert energy that feels whimsical, not kitschy.
- Pantry-friendly: pineapple rings, maraschino cherries, and brown sugar do most of the heavy lifting.
- Kid- and apéro-approved — easy to serve, no slicing drama.
- Freezer stash potential: they thaw like a dream when future-you needs a sweet win.
Tips, Tricks & Variations
- Pan swap: A muffin tin works perfectly. Just don’t skip the generous nonstick spray — sugar caramel is clingy.
- Cherry hack: Swap maraschinos for fresh pitted cherries if you want less syrupy-sweet.
- Upgrade move: Add a splash of rum or bourbon to the caramel mix for a grown-up island vibe.
- Storage: These keep well at room temp for two days, or freeze and rewarm for a just-baked moment.
Serving & Pairings
Serve warm with a dollop of whipped cream or a melting scoop of vanilla ice cream. Or — lean into the apéro spirit and pair with a spiced rum cocktail for maximum smugness.
FAQ
Can I make these ahead of time?
Yes — bake, cool, and store airtight. Flip them out right before serving to keep the tops glossy.
Do I have to use maraschino cherries?
Nope. They’re traditional, but fresh cherries or even dried cranberries work for a tart counterpoint.
Can I use pineapple tidbits instead of rings?
Yes, just layer them into a mosaic at the bottom of each tin — more caramel coverage, less symmetry.
Mini Pineapple Upside-Down Cakes
Ingredients
- 1 can pineapple slices drained (reserve the juice)
- 12 maraschino cherries
- 1/2 cup unsalted butter melted
- 3/4 cup packed brown sugar
- 1 1/2 cups all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/4 teaspoon salt
- 1/2 cup granulated sugar
- 1/4 cup vegetable oil
- 2 large eggs
- 1 teaspoon vanilla extract
- 1/2 cup pineapple juice reserved from the can
Instructions
- Preheat your oven to 350°F (175°C). Grease a muffin tin or line it with cupcake liners.
- In each muffin cup, place one pineapple slice. If needed, cut the slices to fit the size of the cups. Place a maraschino cherry in the center of each pineapple slice.
- In a small bowl, combine the melted butter and brown sugar. Mix well until the sugar has dissolved. Spoon the mixture evenly over the pineapple slices and cherries.
- In a separate bowl, whisk together the flour, baking powder, and salt.
- In a large mixing bowl, beat together the granulated sugar, vegetable oil, eggs, and vanilla extract until well combined.
- Gradually add the dry ingredients to the wet ingredients, alternating with the pineapple juice. Begin and end with the dry ingredients, mixing until just combined. Do not overmix.
- Spoon the batter over the pineapple slices in the muffin cups, filling each cup about 3/4 full.
- Place the muffin tin in the preheated oven and bake for 20-25 minutes, or until a toothpick inserted into the center of a cake comes out clean.
- Remove the muffin tin from the oven and let it cool for a few minutes. Then, carefully invert the tin onto a wire rack or serving platter to release the mini pineapple upside-down cakes. Allow them to cool completely before serving.
- Serve the mini pineapple upside-down cakes as they are, or you can add a dollop of whipped cream or a scoop of vanilla ice cream on top for extra deliciousness