Pineapple Upside-Down Cake

The first time I made this cake, my kitchen smelled like a carnival. That caramelized brown sugar and pineapple scent hit me before I even opened the oven door. My roommate wandered in from her room, asking what bakery I had secretly visited. Nothing beats that moment of inversion when the cake reveals its glistening fruit topping.

I brought this to a summer potluck last year, and it disappeared before the burgers even hit the grill. My friend Sarah asked for the recipe right there, standing with an empty plate. Theres something about this retro dessert that makes people immediately comfortable, like theyve been eating it their whole lives even if they havent.

Ingredients

• Unsalted butter: Use real butter here, nothing else creates that rich caramel base properly
• Light brown sugar: Packed tight, this becomes the sticky glaze that holds everything together
• Canned pineapple rings: Drain them well but save the juice, it adds incredible depth to the batter
• Maraschino cherries: These pop against the golden pineapple and add that classic diner look
• Softened butter: Room temperature butter incorporates air into the batter for a lighter texture
• Granulated sugar: Cream this thoroughly with the butter until the mixture looks pale and fluffy
• Large eggs: Add them one at a time, each one fully incorporated before the next
• Vanilla extract: Pure extract makes a difference you can taste in the final cake
• All-purpose flour: Measure by spooning into the cup and leveling off for accuracy
• Baking powder: This gives the cake its rise and tender crumb structure
• Salt: Just a pinch balances all that sugar and enhances the vanilla
• Whole milk: The fat content matters here, creating a moister cake than skim would

Instructions

Preheat and prepare the pan:

Get your oven to 175°C (350°F) and grease a 23-cm (9-inch) round cake pan thoroughly

Create the caramel layer:

Melt 60 g butter right in the pan, then sprinkle the brown sugar evenly across the bottom

Arrange the fruit:

Place pineapple rings over the sugar and tuck a cherry into the center of each ring

Cream the butter and sugar:

Beat 120 g softened butter and granulated sugar until the mixture turns light and fluffy

Add the eggs and vanilla:

Beat in eggs one at a time, then stir in the vanilla extract until fully combined

Mix the dry ingredients:

Whisk together flour, baking powder, and salt in a separate bowl

Combine wet and dry:

Add flour mixture in three parts, alternating with milk, starting and ending with flour

Layer the batter:

Spoon the batter gently over the fruit arrangement and smooth the top carefully

Bake to golden:

Bake for 38 to 42 minutes until a toothpick in the center comes out clean

The big reveal:

Cool for 10 minutes, run a knife around the edges, then invert onto a serving plate

Save

My grandmother made this for Sunday dinners when I was growing up. She had this one pan she swore by, an old aluminum number with scratches and dents. Every time I use my own version of that pan, I think about her hands arranging those cherries so deliberately.

Serving Suggestions

Warm slices with a scoop of vanilla ice cream create the perfect temperature contrast. The cold cream melting into the warm caramel is something you have to experience. Whipped cream works beautifully too, especially if you fold in a little pineapple juice.

Make It Your Own

Fresh pineapple works wonderfully but needs to be caramelized in a skillet first. Pecans nestled between the rings add a nutty crunch that complements the soft cake. Some bakers swap cherries for cranberry sauce during the holidays for a festive twist.

Storage Tips

This cake keeps beautifully at room temperature for up to two days, covered with a dome or overturned bowl. The caramel actually gets better as it sits. For longer storage, wrap individual slices and freeze them.

• Refrigerate only if your kitchen runs very warm, the caramel can get sticky
• Bring chilled cake to room temperature before serving for the best texture
• Freeze slices on a baking sheet first, then wrap individually to prevent sticking

Save

Every time I serve this cake, someone asks for the recipe. Theres something universally comforting about that combination of flavors, like a warm hug from the past.

Questions & Answers

→ Should I serve this cake warm or at room temperature?

Either way works beautifully. Warm highlights the caramel topping, while room temperature lets the flavors fully develop. Let it cool at least 10 minutes before inverting.

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works well. Slice it into rings and pat dry before arranging. Fresh pineapple may be slightly less sweet, so adjust brown sugar to taste.

→ How do I know when the cake is done baking?

Insert a toothpick into the center of the cake. If it comes out clean or with just a few moist crumbs, it's ready. The top should be golden brown and spring back when touched lightly.

→ Can I make this cake ahead of time?

Bake it up to one day in advance. Store covered at room temperature. The flavors actually develop better overnight. Reheat briefly before serving if desired.

→ What can I use instead of maraschino cherries?

Pecan halves make an excellent nutty alternative. Fresh berries like raspberries or cranberries also work. Consider candied ginger for a spiced twist on the classic.