Gluten-Free Pineapple Upside Down Cake

Total Time: 1 Hour 5 Minutes
 
 Yield: 10–12 Slices 1x
 
 Diet: Gluten Free

This classic gluten-free pineapple upside down cake features a moist, tender buttery cake topped with caramelized pineapple rings and vibrant maraschino cherries. Baked to golden perfection, it flips into a beautiful, retro-inspired dessert with a sweet, tropical flavor in every bite. The recipe can be made gluten-free, dairy-free, vegan, or regular.

Topping

• 1 can (398ml) pineapple slices in juice
• 15–20 maraschino cherries *see note
• 1/4 cup (57g) salted butter, melted
• 1/2 cup (100g) brown sugar

Cake

• 1 1/2 cups (180g) gluten-free flour 1:1 baking blend
• 1 teaspoon baking powder
• 1/2 teaspoon fine sea salt
• 1/4 teaspoon baking soda
• 1/3 cup (80ml) milk *regular or plant-based
• 1/4 cup (60ml) pineapple juice, reserved from the canned pineapple slices
• 1/4 cup (60ml) sour cream, full-fat *regular or plant-based
• 1/2 cup (114g) salted butter, room temperature *regular or plant-based
• 3/4 cup (150g) granulated sugar
• 2 large eggs, room temperature

Instructions

Preheat the oven to 350ºF.

1. Place the pineapple rings and maraschino cherries on a clean dish or paper towel and pat dry.
2. Pour the melted butter into an 9-inch round cake pan. Swirl around and brush it up the sides of the pan.
3. Sprinkle the brown sugar over the bottom of the pan.
4. Place a pineapple ring in the center of the pan on top of the brown sugar. Continue to place pineapple rings around it until the pan is covered.
5. Put a cherry in and between each pineapple ring.
6. Press the pineapples and cherries down firmly so they are in contact with the pan itself. Set aside.
7. Combine the flour, baking powder, salt, and baking soda in a small bowl.
8. Whisk together the milk, sour cream, and pineapple juice in a separate small bowl.
9. In a stand mixer or large mixing bowl with an electric mixer, cream the butter and sugar on high until light and fluffy. This should take approximately 2-3 minutes.
10. Add the eggs and mix until fully combined. Scrape down the sides of the bowl when necessary.
11. With the mixer on low, add approximately half of the flour mixture, followed by the milk mixture, and finish with the remaining of the flour mixture. Mix for approximately 20-30 seconds between each addition.

1. Gently spread the cake batter over the pineapples and cherries and smooth evenly.
2. Bake for 30 minutes before removing to cover with foil. Return the covered cake to the oven and bake for a final 10-15 minutes, or until a toothpick comes out with a few moist crumbs.
3. Allow the cake to cool in the pan for 20 minutes before inverting on a plate, cake stand, or serving platter to fully cool. Helpful hint: run a butterknife around the edges of the pan before inverting the cake to help release any caramelized edges. Enjoy!
4. Store leftover cake in an airtight container in the fridge for up to 5 days.