When I was a kid, my mom pulled out the shiny tube pan and a can of pineapple like she had a secret ingredient for instant sunshine. The kitchen smelled like warm butter and brown sugar, and I sat on a stool, swinging my legs while she arranged the pineapple rings with the meticulousness of an artist. That sticky, caramel top—amber and glossy—felt like dessert alchemy. This Pineapple Upside Down Cake takes me right back to that sticky, happy kitchen: the soft crack of the top when it cooled, the bright pop of cherries, and the first warm bite where sweet caramel meets tender cake. You’ll get that same cozy, retro charm with minimal fuss.
Quick Facts
- Yield: Serves 8
- Prep Time: 20 minutes
- Cook Time: 35 minutes
- Total Time: 55 minutes
Why This Recipe is Awesome
It’s a one-pan showoff that tastes like a warm hug. The top caramel creates shiny, sticky pockets of flavor, the pineapple brings bright acidity, and the cake stays tender and moist. It’s an easy retro dessert that feels fancy without drama—perfect for potlucks, weeknights, or when you need a nostalgic treat. Honestly, it’s so forgiving even your oven can’t mess it up.
Ingredients
For the Main Dish:
- 6 tbsp unsalted butter (for topping)
- 2/3 cup packed light brown sugar
- 1 (20 oz) can pineapple slices in juice, drained (reserve juice for thinning batter if needed)
- 8–10 maraschino cherries (optional, one per pineapple ring)
- 1 1/4 cups all-purpose flour
- 1 tsp baking powder
- 1/4 tsp salt
- 1/2 cup (1 stick) unsalted butter, softened (for batter)
- 2/3 cup granulated sugar
- 2 large eggs, room temperature
- 1 tsp vanilla extract
- 1/3 cup sour cream (or plain Greek yogurt)
- 1/3 cup whole milk
For the Sauce / Garnish (if applicable):
- Vanilla ice cream or whipped cream, for serving (optional)
- Extra sliced pineapple or toasted coconut for garnish (optional)
How I Make It
Step 1:
Preheat the oven to 350°F. In a 9-inch round cake pan, melt 6 tbsp unsalted butter over low heat on the stovetop or microwave until foamy. Stir in 2/3 cup packed brown sugar until the mixture looks glossy and slightly syrupy. Pour and spread that caramel into the bottom of the pan—this will become your shiny top. Arrange pineapple rings in a single layer and tuck a cherry into each center if you like. I warn you: the smell of butter and brown sugar will make you impatient for the finish.
Step 2:
Whisk together 1 1/4 cups all-purpose flour, 1 tsp baking powder, and 1/4 tsp salt in a bowl. In a separate bowl, beat 1/2 cup softened butter with 2/3 cup granulated sugar until creamy and pale (about 2 minutes). Add eggs one at a time, beating after each, then stir in 1 tsp vanilla. Fold in half the dry mix, then the 1/3 cup sour cream, then the rest of the dry mix, finishing with 1/3 cup milk to keep the batter silky. Don’t overmix—stop when everything blends together and looks smooth.
Step 3:
Spoon the batter gently over the pineapple, spreading carefully so you don’t tear the rings—use an offset spatula or the back of a spoon. The batter will nestle around the fruit. Slide the pan into the oven and bake at 350°F for about 35 minutes, or until the cake turns golden and a toothpick comes out with a few moist crumbs. You’ll smell warm vanilla and brown sugar as the edges caramelize.
Step 4:
Let the cake rest for 10 minutes on a wire rack after you take it out—this gives the caramel time to set slightly so it unmolds cleanly. Run a thin knife around the edge to loosen, then place a serving plate over the pan and invert in one confident motion. If a few pineapple pieces cling to the pan, just scoop them back on top. The top should gleam and the cake should peel away easily.
Step 5:
Serve warm or at room temperature. Scoop vanilla ice cream alongside, or dollop whipped cream. For a finishing touch, sprinkle a little flaky sea salt or grate a bit of fresh lime zest over the top to brighten the sweetness. Listen for that satisfying fork scrape when someone digs in—pure joy.
Pro Tips
- Use room-temperature eggs and butter for a smoother, fluffier batter—cold ingredients slow down mixing.
- If your pan isn’t nonstick, line it with parchment and leave an overhang to help lift the cake if needed.
- Warm the pineapple a bit before arranging if it feels too cold—the caramel bonds better to slightly warm fruit.
- If you like extra caramel, stir 1–2 tbsp of reserved pineapple juice into the brown sugar mixture before pouring it in the pan.
Common Mistakes to Avoid
- Skipping preheating: Classic rookie move. It changes texture and bake time.
- Overmixing: Leads to dense or chewy results. Mix until just combined.
- Guessing cook time: Always use visual cues or a timer, not just vibes.
- Overcrowding pans: Give your food some breathing room to crisp properly.
Alternatives & Substitutions
- Use fresh pineapple slices instead of canned for brighter flavor; bake a few minutes longer if fruit is very juicy.
- Substitute Greek yogurt for sour cream to add tang and reduce richness; expect a slightly denser crumb.
- For a dairy-free version, swap butter for a vegan butter and use coconut milk instead of whole milk; the cake will take on a subtle coconut note.
- Make it gluten-free with 1:1 gluten-free baking flour—texture will be slightly crumbly but still delicious.
Variations & Tips
- Rum-Glazed: Add 2 tbsp dark rum to the brown sugar mixture for a boozy depth—perfect for grown-up gatherings.
- Coconut Pineapple: Fold 1/3 cup shredded toasted coconut into the batter for a tropical twist.
- Mini Upside-Down Cakes: Bake in a muffin tin lined with pineapple and cherry for individual servings—reduce bake time to 18–22 minutes.
- Peach Upside-Down: Swap pineapple for sliced peaches in late summer; cinnamon in the batter complements the fruit.
- Streusel Top: Sprinkle a thin oat streusel over the batter before baking for a crunchy contrast to the gooey top.
FAQ (Frequently Asked Questions)
- Can I make this ahead of time?
- Yes! Bake the cake and let it cool completely, then wrap tightly and store at room temperature for up to 24 hours or in the fridge for 3 days. Rewarm gently in a 350°F oven for 8–10 minutes before serving, or microwave single slices for 10–15 seconds and top with ice cream.
- Can I double the recipe?
- Sure thing. Use a 9×13-inch pan for a doubled batch and bake at 350°F, but increase the bake time to about 40–45 minutes and check with a toothpick for doneness. The bigger pan creates more caramel, so watch the edges.
- Can I substitute butter with oil?
- Technically yes, but you’ll miss that buttery magic. Use ¾ the amount of oil (so about 3/4 stick worth translates to roughly 6 tbsp oil) and expect a slightly less rich flavor and softer crust.
- How do I know it’s done?
- Look for a golden top and slightly pulled-away edges. A toothpick inserted into the center should come out with a few moist crumbs—not wet batter. The cake should feel springy when you press it gently.
- What if I don’t have ingredient X?
- Swap pantry staples: no sour cream? Use plain yogurt. Out of brown sugar? Mix granulated sugar with a teaspoon of molasses per cup to mimic it. No maraschino cherries? Halved fresh cherries work great.
How I Like to Serve It
I love this cake warm from the oven with a scoop of cold vanilla ice cream that slowly melts into the caramel. It shines at summer BBQs and brings retro charm to a holiday table. For a cozy night in, pair slices with strong coffee or a dollop of whipped cream and watch the room get quieter in the best possible way.
Notes
- Store leftovers covered at room temperature for 1 day, or refrigerated up to 3 days. Reheat gently to revive the caramel.
- If using fresh pineapple, cook a few extra minutes and remove excess juice with a paper towel so the cake doesn’t get soggy.
Final Thoughts
Closing: Now go impress someone — or just yourself — with your homemade masterpiece!