Save My grandmother kept pineapple rings in the cupboard year-round, tucked behind the cereal boxes like they were something special. I never understood why until the afternoon she pulled everything out and taught me this cake. We stood in her tiny kitchen watching the butter and sugar bubble together, and suddenly it made perfect sense. The smell of caramelizing pineapple filled every corner of the house, drawing my grandfather in from the garage. That first flip onto the plate felt like magic, revealing those glossy cherries and golden rings in perfect formation.
Last summer I made this for a neighborhood potluck, carried it over still warm from the oven. My neighbor Sarah took one bite and immediately asked for the recipe, saying it reminded her of birthdays at her aunts house in the 1970s. Three people asked if I had ordered it from a bakery, which might be the best compliment I have ever received. Now it is my go-to whenever I need something that feels nostalgic but tastes even better than you remember.
Ingredients
- Unsalted butter: Use real butter here, nothing substitutes well for that rich flavor in both the topping and the cake
- Light brown sugar: Packed tight creates the perfect caramel layer that keeps the pineapple moist and gooey
- Canned pineapple rings: Drain them well and pat dry with paper towels to prevent excess moisture
- Maraschino cherries: These pop against the golden pineapple and add that classic retro look
- Granulated sugar: Creamed with butter until fluffy gives the cake its tender, melt-in-your-mouth texture
- Large eggs: Room temperature eggs incorporate better and create a more stable batter
- Vanilla extract: Pure vanilla makes all the difference in a cake with so few ingredients
- All-purpose flour: Scooped and leveled, not packed, for accurate measurements
- Baking powder: Fresh baking powder ensures the cake rises properly and stays light
- Salt: Balances all that sweetness and brings out the vanilla notes
- Whole milk: Creates a tender crumb and helps bind everything together
Instructions
- Preheat your oven:
- Set it to 175°C (350°F) and grease a 23-cm (9-inch) round cake pan thoroughly with butter or cooking spray.
- Make the caramel topping:
- Melt 60 g butter in the prepared pan, then sprinkle brown sugar evenly over the top. It will look clumpy and uneven, but it melts beautifully in the oven.
- Arrange the fruit:
- Place pineapple rings over the sugar mixture and nestle a maraschino cherry in the center of each ring.
- Cream the butter and sugar:
- Beat 120 g softened butter and granulated sugar together until light and fluffy, about 3 minutes.
- Add the eggs:
- Beat in eggs one at a time, then add vanilla extract, scraping down the sides of the bowl.
- Mix the dry ingredients:
- Whisk together flour, baking powder, and salt in a separate bowl.
- Combine everything:
- Add the flour mixture to the batter in three additions, alternating with milk, beginning and ending with flour. Mix until just combined, do not overmix.
- Assemble the cake:
- Spoon the batter evenly over the pineapple rings and smooth the top carefully.
- Bake until golden:
- Bake for 38 to 42 minutes, or until a toothpick inserted into the center comes out clean.
- Flip and serve:
- Let cool in the pan for 10 minutes, run a knife around the edges, then invert onto a serving plate.
Save My sister called me last month completely panicked because she had agreed to bring dessert to her in-laws anniversary dinner. I walked her through this recipe over the phone, just like our grandmother had done with me years ago. She sent me a picture later that evening, the cake sitting perfectly on a vintage cake stand with a slice already missing. Sometimes the simplest recipes become the most treasured memories.
Making It Your Own
I have experimented with fresh pineapple when it is in season, though it requires a bit more prep time to slice into even rings. Canned pineapple works beautifully because the natural juices have already developed that deep sweetness. Sometimes I swap pecan halves for the cherries, especially in autumn when I am craving something a little more nutty and warm.
The Perfect Invert
The moment of inversion still makes me hold my breath every single time. I place my serving plate upside down over the pan, count to three, and flip with one confident motion. That first peek underneath to see if everything stayed in place never gets old. Serve it warm if you can, that caramel is still gooey and the pineapple has this incredible tender texture that softens as it cools.
Serving Suggestions
Whipped cream is the classic pairing, but I have also served it with vanilla ice cream for an extra indulgent dessert. The sweetness of the cake stands up beautifully to a cup of strong black coffee or even a splash of dark rum if you are serving it to adults. This cake actually improves overnight as the flavors meld together, making it perfect for making ahead.
- Leftovers keep well covered at room temperature for up to two days
- Warm individual slices in the microwave for 15 seconds to recapture that just-baked texture
- The caramel layer stays gooier if you avoid refrigerating the cake
Save There is something deeply satisfying about a dessert that looks so impressive yet comes from such humble ingredients. Every time I make this, I think about all the kitchen tables it has graced over the decades.
Recipe FAQs
- → Should I serve pineapple upside-down cake warm or cold?
Warm is ideal! The cake is most delicious when served within 30 minutes of baking, as the caramel topping is still slightly gooey. That said, it also tastes wonderful at room temperature and can be made ahead for gatherings.
- → Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple works beautifully and adds even more vibrant flavor. Just slice it into rings about 1/2 inch thick. You may need to cook it a few extra minutes since fresh pineapple contains more moisture than canned.
- → How do I know when the cake is done baking?
Insert a wooden toothpick into the center of the cake—if it comes out clean or with just a few moist crumbs, it's ready. The edges should also pull slightly away from the pan, and the top will be golden brown.
- → Can I make this cake ahead of time?
Yes! Bake the cake up to 24 hours in advance. Once cooled, cover tightly with plastic wrap or store in an airtight container. Before serving, you can gently reheat individual slices in the microwave for 15-20 seconds to recapture that freshly-baked warmth.
- → What can I substitute for maraschino cherries?
Pecan halves are a classic Southern twist and add wonderful crunch. You could also use fresh cranberries, drained canned peach slices, or simply omit them entirely—the pineapple shines on its own!
- → Why did my cake stick to the pan?
This usually happens if the cake cooled too long before inverting. The caramel sets as it cools, so flip the cake after exactly 10 minutes of cooling. Running a knife around the edges first also helps release it cleanly.