Pineapple Upside-Down Cupcakes: Mini Retro Treats With Big Tropical Flavor

1. Preheat oven to 350°F (175°C).
2. Grease a 12-cup muffin tin well (don’t use paper liners—these need to flip out cleanly).

2) Build the topping in each cup

1. Mix brown sugar and melted butter in a small bowl.
2. Spoon about 1 to 1 1/2 teaspoons of the mixture into each muffin cup.
3. Add pineapple: use a small chunk or a piece cut from a ring to fit the cup.
4. Place a cherry in the center of the pineapple (or off-center for a fun look).

3) Make the cupcake batter

1. In a bowl, whisk flour, baking powder, and salt.
2. In another bowl, beat softened butter and sugar until light and fluffy (2–3 minutes).
3. Add eggs one at a time, mixing after each. Stir in vanilla.
4. Add dry ingredients in two additions, alternating with milk (and pineapple juice if using).
5. Mix just until combined—don’t overmix.

4) Fill and bake

1. Spoon batter into muffin cups over the topping, filling each about 2/3 full.
2. Bake 18–22 minutes, until tops spring back and a toothpick comes out clean.

5) Flip (the important part)

1. Let cupcakes cool in the pan for 5 minutes (not too long, or caramel can stick).
2. Run a thin knife around edges if needed.
3. Place a tray over the pan and carefully invert to release cupcakes.
4. Let them sit a minute, then lift the pan. Spoon any extra caramel from the pan over the tops.

Serving and Storage:

Serve pineapple upside-down cupcakes slightly warm or at room temperature. They’re delicious on their own, but a little
whipped cream turns them into a full-on dessert moment.

• Room temperature: 1 day (covered).
• Refrigerator: up to 4 days in an airtight container. Bring to room temp before serving.
• Reheat: 10–15 seconds in the microwave for a warm caramel finish.
• Freezing: possible up to 1 month, but the topping may soften when thawed.

Tips:

• Drain pineapple well: excess liquid can thin the caramel and make cupcakes soggy.
• Grease the pan: these must release cleanly—grease is non-negotiable.
• Flip while warm: 5 minutes is the sweet spot for easy release.
• Don’t overfill: too much batter can overflow and mess up the flip.
• Cut pineapple to fit: smaller pieces give the prettiest cupcake tops.

Variations:

• Rum flavor: add 1 tbsp rum to the caramel topping for a tropical twist.
• Coconut cupcakes: replace some milk with coconut milk and add coconut extract.
• Spiced version: add a pinch of cinnamon to the batter.
• Cherry-free: skip cherries and use extra pineapple or a berry instead.
• Mini cupcakes: use a mini muffin tin and bake 10–12 minutes.

Conclusion:

Pineapple Upside-Down Cupcakes are the perfect mini version of a beloved classic: buttery brown sugar caramel, bright pineapple
flavor, and a cherry on top (literally). They look impressive, taste nostalgic, and are easy enough for any day you want a
sweet treat that feels special. Bake them once, and you’ll understand why these “retro” cupcakes keep coming back.

FAQ:

Can I use fresh pineapple?

Yes. Cut it small and drain/press lightly so it doesn’t release too much juice while baking.

Do I need cupcake liners?

No—liners won’t flip properly. Grease the pan instead.

Why didn’t my cupcakes release cleanly?

Most often, the pan wasn’t greased enough, or the cupcakes cooled too long before flipping. Flip at around 5 minutes.

Can I make these in advance?

Yes. They taste great the next day. Store airtight and bring to room temperature before serving.

What’s the best way to serve them?

Room temperature with whipped cream, or slightly warm for extra gooey caramel goodness.