Pineapple Upside Down Cake – with a twist has a secret ingredient that adds a unique flavor and richness to this cake. Upside-down cakes are a delightful and visually striking dessert that flips conventional baking on its head, quite literally! If you love them I suggest also trying Rhubarb Blueberry Upside-Down Cake.
Key Takeaways:
- Maple Syrup is the Game Changer: Instead of the usual brown sugar and butter topping, this recipe uses reduced real maple syrup for a deep, rich flavor that doesn’t make the cake soggy.
- Topping is Simple & Sweet: You only need four ingredients—butter, boiled maple syrup, canned pineapple slices, and maraschino cherries. Use unsweetened pineapple to let the maple shine.
- Dense Yet Moist Cake Base: The cake is structured like a coffee cake—dense enough to hold the topping, yet moist thanks to buttermilk and cake flour.
- Bright Flavor Boost: Lemon and vanilla are added to the batter to enhance the tropical flavor and freshness.
- No Fancy Tools Required: A handheld mixer is all you need. The process is straightforward—cream, mix, alternate, and bake.
- Baking Tip for Perfection: Bake at 350°F for 45 minutes (cover with foil halfway to avoid overbrowning), and invert while still warm for best presentation and taste.
Overview
This Pineapple Upside-Down Cake takes a beloved retro dessert and gives it a flavor-packed upgrade with one secret ingredient—real maple syrup. Instead of the traditional brown sugar and butter topping, this recipe calls for maple syrup that’s boiled down to a rich, thick glaze. This not only enhances the caramelized pineapple layer but also prevents the cake from becoming soggy. With a moist, dense crumb similar to a coffee cake—thanks to buttermilk and cake flour—this treat can hold up to the juicy fruit topping without collapsing. Infused with bright lemon and vanilla, the cake itself offers a balanced, slightly tropical flavor profile. Simple yet impressive, it’s baked to golden perfection and best served warm. Whether you’re hosting a brunch, celebrating a special occasion, or just craving something nostalgic with a twist, this dessert delivers on both taste and presentation.
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What is The Secret Ingredient in this Pineapple Upside Down Cake?
The extra yum and extra flavor in this cake is from maple syrup. Not just maple syrup straight from the container. I boil the maple syrup down to make it an extra thick syrup that won’t turn the cake soggy. The flavor is sooo good that once you use maple syrup, you won’t return to brown sugar and butter. A word of advice: the maple syrup has to be real maple syrup. No artificial syrup is allowed.
What you will need:
The topping is super simple. Four ingredients. Butter, maple syrup, canned pineapple slices, and maraschino cherries. Use unsweetened pineapple slices as the maple syrup topping will sweeten them to perfection.
The cake batter is a somewhat dense, rich, and moist cake. It is similar to a coffee cake. The cake needs to be a little dense because of the weight of the pineapple topping on the hot cake tends to compress it. A light fluffy cake wouldn’t hold up to the weight. However, I use cake flour instead of all-purpose flour. Also buttermilk instead of regular milk adds extra moisture to the cake.
The flavoring in the cake is a combination of lemon and vanilla. The lemon brightens the flavor and give the cake a little extra topical vibe.
How to Make the Cake - Step by Step
Make the Topping:
- Boil 1 cup of maple syrup down to 3/4 of a cup. When the syrup cools, it will become super thick. That is what should happen.
- Cover a 10 in baking pan with a piece of parchment an add add the syrup and butter mixture. Arrange the pineapple and maraschino cherries.
Make the Cake:
- Mix together the dry ingredients and set aside.
- For this cake you don’t need a stand mixer. A hand held mixer works great to cream the butter and sugar together. It is also used to beat in the eggs and flavoring.
- Alternate the flour mixture with the buttermilk. Add in 3 batches each starting with the milk and ending with the flour.
- Don’t overmix the batter, a spatula works great for mixing in the milk and flour.
Bake and Serve the Cake
- Spoon the batter (it is thick) over the pineapple slices in the pan and bake at 350 degrees for 30 minutes. To prevent overbrowning, cover with foil and bake another 15 minutes. 45 minutes total.
Make the Cake:
- Mix together the dry ingredients and set aside.
- For this cake you don’t need a stand mixer. A hand held mixer works great to cream the butter and sugar together. It is also used to beat in the eggs and flavoring.
- Alternate the flour mixture with the buttermilk. Add in 3 batches each starting with the milk and ending with the flour.
- Don’t overmix the batter, a spatula works great for mixing in the milk and flour.
Bake and Serve the Cake
- Spoon the batter (it is thick) over the pineapple slices in the pan and bake at 350 degrees for 30 minutes. To prevent overbrowning, cover with foil and bake another 15 minutes. 45 minutes total.
- Let the cake cook 15 minutes before inverting onto a serving platter.
- Loosen the edges of the cake from the pan. To invert, cover the cake with a platter to form a cake pan, cake platter sandwich. Then flip the cake over onto the platter. Remove the cake pan – carefully – the cake is still very hot.
- The cake is best when served fresh and warm. What isn’t better fresh and warm?
For another dessert idea try Creamy Cheese Cake or Lemon Blueberry Pound Cake.
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FAQ:
Q: What makes this pineapple upside down cake different from the classic version?
A: The secret ingredient is reduced real maple syrup, which adds rich depth and prevents the cake from becoming soggy, unlike the traditional brown sugar topping.
Q: Can I use pancake syrup instead of real maple syrup?
A: No—only real maple syrup works for this recipe. Artificial syrups won’t reduce properly or give the same depth of flavor.
Q: Why does the cake need to be dense?
A: A dense cake base is essential because it supports the heavy pineapple topping and prevents the cake from collapsing or getting compressed.
Q: Do I need a stand mixer for this recipe?
A: Not at all! A simple handheld mixer is sufficient for creaming and mixing the batter.
Q: How do I keep the cake from overbaking or burning on top?
A: Bake uncovered for 30 minutes, then cover with foil for the remaining 15 minutes to prevent overbrowning.
Q: Can this be made ahead of time?
A: It’s best served fresh and warm, but you can make it earlier in the day and warm it slightly before serving for the ideal texture and flavor.
Pineapple Upside Down Cake - With a Twist
Equipment
- 10 inch deep dish pie plate of 10 inch cake pan
Ingredients
Pineapple Topping
- 1 cup Maple Syrup
- 10 Pineapple Rings
- Maraschino Cherries (about 20)
- 2 tbsp melted Butter
Cake
- 1½ cups Cake Flour (180g)
- 1 tsp Baking Powder
- ¼ tsp Baking Soda
- ¼ tsp Sea Salt
- ½ cup Unsalted Softened Butter (113g)
- ¾ cup Sugar
- 1 tsp Vanilla
- 1 tsp Lemon Extract
- ½ cup Buttermilk
- 2 Eggs Room Temperature
Instructions
Pineapple Topping
- Gently boil the 1 cup of maple syrup to reduce it to 3/4 of a cup of very thick syrup.
- Line the bottom of the pie or cake place with a piece of parchment.
- Add the melted butter and thickened maple syrup to the dish. Stir to mix.
- Arrange the pineapple slices and maraschino cherries in the dish. (see the picture of a finished cake) Set Aside
Make the Cake
- Preheat oven to 350 degrees F. (170 degrees C)
- Mix together the cake flour, baking powder, soda, and salt. Set aside.
- With a hand or stand mixer beat the sugar and the butter until fluffy.
- Add the eggs one at a time, mix well after each egg.
- Add the vanilla and lemon and mix in.
- Alternate the flour with the buttermilk. Add 1/3 at a time and mix in by hand after each addition. Begin and end with the flour. An electric mixer will over-mix the batter.
- Spoon the batter on top of the prepared pineapple and cherries in the pie dish. Spread to evenly fill the pan.
- Bake for 30 minutes and then cover with a piece of foil and bake another 15 minutes. The total baking time is 45 minutes.
- Remove from oven and let cool for 15 minutes before inverting on a serving place. Best when eaten fresh and warm.
