This classic Gluten Free Pineapple Upside Down Cake is a comforting, nostalgic dessert that’s moist, simple to prepare, and full of tropical flavor. Ideal for celebrations, potlucks, or an easy weekend treat, this recipe delivers a tender cake topped with caramelized brown sugar, juicy pineapple rings, and bright maraschino cherries—without gluten.
If you enjoy easy gluten-free baking, you might also like other simple desserts such as gluten-free Oreo balls, gluten-free pumpkin cupcakes, fried gluten-free donuts, gluten-free carrot cake, or peanut butter oatmeal bars. These options pair well with this pineapple cake for a dessert table.
Why I love this pineapple upside down recipe
- Gluten-free and crowd-pleasing: Made with a reliable gluten-free yellow cake mix and simple pantry ingredients, this dessert is friendly for guests who need gluten-free options while remaining irresistibly classic.
- Fast and accessible: Using a boxed cake mix keeps the recipe straightforward and quick—great for last-minute gatherings or when you want an easy homemade dessert.
- Flexible for serving: Bake it as one large 9×13 pan or divide the batter into individual pans or muffin tins for mini upside down cakes.
- Tropical flavor: The brown sugar caramel, canned pineapple rings, and maraschino cherries deliver a bright, sweet finish that balances the cake’s tender crumb.
Ingredients needed
- 22 ounce gluten-free yellow cake mix (choose a trusted brand)
- ½ cup butter, softened (plus an additional ½ cup sliced into small squares for the pan)
- 2 tablespoons oil
- 4 eggs
- ⅔ cup milk
- 1 cup brown sugar
- 8 canned pineapple rings (drained)
- 8 maraschino cherries
How to make a Gluten-free Pineapple Upside-Down Cake
- Preheat: Preheat your oven to 350°F (175°C).
- Mix the batter: In a large bowl or stand mixer, combine ½ cup softened butter, 2 tablespoons oil, 4 eggs, and ⅔ cup milk. Mix until well combined. Gradually whisk in the 22-ounce gluten-free cake mix until the batter is smooth and even.
- Prepare the pan: In a 9×13 glass baking pan, arrange the additional ½ cup butter cut into small squares across the bottom. Sprinkle 1 cup of brown sugar evenly over the butter so it will melt and form a caramel as the cake bakes.
- Add the fruit: Place the drained pineapple rings on top of the brown sugar mixture, spacing them evenly. Set a maraschino cherry in the center of each pineapple ring.
- Pour the batter: Pour the prepared cake batter evenly over the pineapple rings and cherries. Tap the pan gently a few times so the batter settles around the fruit.
- Bake: Bake at 350°F for approximately 30–32 minutes, or until the top is golden and a toothpick inserted into the center comes out clean.
- Cool and invert: Remove the pan from the oven and let it rest for a couple of minutes. Carefully invert the cake onto a large wooden cutting board or baking sheet so the pineapple and cherries are on top. If the caramel seems sticky, allow the pan to cool slightly before flipping to avoid spills.
- Serve: Slice and serve warm or at room temperature. For an extra treat, serve each slice with a scoop of vanilla ice cream.
Make ahead, storage, and freezing instructions
Make ahead: You can bake this cake a day or two in advance. Once cooled, keep it in an airtight container until ready to serve to preserve moisture and flavor.
Storage: After the cake reaches room temperature, store leftovers in an airtight container at room temperature for 2–3 days. Refrigeration is not required but will extend freshness; if refrigerated, allow slices to come to room temperature before serving.
Freezing: Yes—this cake freezes well for up to three months. Wrap tightly in plastic wrap or place in a freezer-safe container. Thaw overnight in the refrigerator before serving.
Recipe variations
- Coconut crunch: Sprinkle toasted shredded coconut over the cake just before serving for extra texture and tropical flavor.
- Nutty topping: Scatter chopped pecans, macadamia nuts, or pistachios on top for a crunchy contrast.
- Chocolate twist: Drizzle melted chocolate or warm hot fudge over slices for a decadent finish.
More dessert recipes
- Creamy gluten-free cheesecake
- Piña colada mocktail (for pineapple lovers)
- Gluten-free apple upside-down cake
- Easy cakesicles for bite-sized treats
Recipe details
Prep Time: 8 minutes
Cook Time: 30–32 minutes
Total Time: About 40 minutes
Servings: 12 slices
Calories: Approximately 283 kcal per slice
Author: Chandice Probst
Can I use fresh pineapple?
Yes. Fresh pineapple chunks or rings can be used in place of canned, but make sure to drain and pat them dry so excess juice does not make the topping too thin. Fresh pineapple will add a slightly different texture and a bright, fresh flavor.
Notes
- When selecting a gluten-free cake mix, pick one you trust for texture and flavor—some brands perform better in upside-down preparations.
- For easier flipping, let the cake cool 2–4 minutes so the caramel sets slightly, then invert carefully onto a large board or tray.
- Serve warm or at room temperature; a scoop of vanilla ice cream pairs especially well with the caramelized topping.