Upside Down Pineapple Cake

there’s a smell that pulls me straight back to my grandmother’s kitchen – rich, warm sugar melting into butter, the dizzying sweetness of pineapple rising up from the oven… and that soft hum of something baking that always felt like a hug in the air. this pineapple upside-down cake, with its glossy golden top and plush, spongey base, is the kind of dessert you don’t just taste – you remember it. the caramel seeps into the cake just a little, the edges turn chewy and sweet, and the whole thing looks so lovely when flipped out onto the plate, like it was always meant to be admired before devoured.

Why You’ll Crave It

• The deep golden caramel melds right into the cake – sweet but not overwhelming, just that perfect cozy balance.
• Pineapple adds brightness and a little tang that keeps the bite interesting (and keeps you going back for more).
• It bakes up beautifully in under an hour, which means more dessert, less waiting.
• It’s gorgeous to serve – really. You flip it over and everyone gasps a little.
• Tastes just as comforting on a rainy afternoon as it does at a birthday table.

The first time I made this for my partner’s parents, I was so nervous – but the smell alone made everyone smile before we’d even sliced it.

What You’ll Need

• Pineapple slices: about 7–8 rings, canned in juice (or fresh, if you’re feeling extra – just slice those fairly thin)
• Cherries: 10 or so, I like to use stemless maraschino cherries for color, right in the center of each pineapple ring
• Brown sugar: 1/2 cup, packed, for that rich sticky base – light or dark, either works
• Butter: 1/4 cup (plus a bit more for greasing the pan), melted and fragrant
• All-purpose flour: 1 cup, spooned and leveled – nothing fancy here, just good quality unbleached flour
• Baking powder: 1 and 1/2 teaspoons, to lift the cake just right
• Sugar: 1/2 cup white granulated – to sweeten the batter evenly
• Eggs: 2 large, room temperature if you can remember ahead of time
• Milk: 1/2 cup whole milk, cold is okay, but room temp helps the batter mix more smoothly

Easy How-To

Get the oven ready first

Set that oven to 200°C (about 400°F) so it can preheat while you do everything else. A hot oven is key.

Butter the pan

Grab a 9-inch round cake pan. Rub it generously with butter to make sure nothing sticks – especially that caramel layer.

Make the brown sugar butter layer

Sprinkle your brown sugar right into the bottom of the pan, then drizzle the melted butter on top. Give it a gentle swirl to coat everything. This becomes the sticky top once you flip it.

Arrange those fruits

Place pineapple slices over the sugar-butter layer – press gently. Slip one cherry into each ring’s center, then maybe a few extras in the gaps if you like. No pressure to make it perfect.

Mix the dry stuff

In a bowl, whisk together the flour, baking powder, and sugar. It’s okay if it’s a bit lumpy still. Better than overmixing.

Add eggs, milk, and melted butter

Crack the eggs in, pour in the milk and that rest of the melted butter. Stir gently until the batter is smooth-ish. Don’t go too hard or it’ll toughen the cake later.

Pour the batter over the fruit

Carefully spoon or pour the batter over the pineapples. Use a spatula to smooth the surface a little. It’s okay if it looks uneven – it levels out in the oven.

Bake to golden heaven

Bake for 30–35 minutes. Look for golden top (which will be the bottom later). A toothpick should come out mostly clean from the center.

Cool… just a bit

Let the cake rest in the pan for 10 minutes. That pause helps the caramel set just enough so it doesn’t all run off when you flip it.

Invert and breathe

Run a thin knife around the edge. Place a large plate or platter over the pan, take a breath, and quickly flip. Lift the pan gently. You’ll see the pineapples shining and golden. Glorious.

Good to Know

• If the caramel sticks a bit, scrape it out and spoon it lovingly back on top. No one minds.
• The cake tastes even better the next day, slightly chilled – it firms up in a lovely way.
• If you don’t have cherries, dried cranberries or berries work too – not traditional, but pretty.

Serving Ideas

• Serve warm with a scoop of vanilla ice cream, or with softly whipped cream scented with a splash of rum.

Top Tricks

• Drain pineapple and cherries well if using canned – too much juice, and your caramel can get wet and runny.

Frequently Asked Questions

Can I make this a day before and still serve it nicely?

Absolutely. Cover it in plastic wrap and keep at room temp, or chill it. Gently reheat slices or serve cold – both work beautifully.

The caramel hardened too quickly before I arranged the fruit – what now?

Don’t worry too much. As soon as it bakes, it melts back down again. Just try to press the fruit in before it cools completely next time.

Is there a way to make it gluten-free?

You can try with a 1:1 gluten-free flour blend. The texture might be slightly different, but still delicious if your flour’s decent.

How do I store leftover pineapple upside-down cake?

Cover it tightly and keep at room temperature for up to 2 days, or refrigerate if you prefer it chilled (I do, actually).

Can I use individual ramekins for mini cakes?

Yes, and they’re adorable. Just be sure to reduce baking time and grease well. Flip each one gently once they cool slightly.