Pineapple Upside Down Bundt Cake Recipe

Traditionally, an amazing homemade pineapple upside down cake, with its ooey gooey brown sugar syrup drenching tangy pineapple and sweet maraschino cherries, is baked in a square or rectangular pan. But this incredible recipe from developer Autumn LeAnn uses a bundt cake pan instead. The benefit of a bundt cake pan is that it produces a beautiful decorative shape with its lines imprinted on the cake. It also concentrates the rich fruit found in this recipe within the moist cake better than in a rectangular-shaped pan.

The prep time to make this cake hovers at just 20 minutes, but the baking time takes anywhere from 60 to 75 minutes. Trust us, it's worth the wait!

"This bundt cake is worth all of the effort!" says LeAnn. "The end product is beautiful and delicious. It's great for any occasion, especially summer cookouts! This cake is fairly dense with just the right amount of sweetness. The pineapple juice adds just enough fruitiness to the batter and the pineapple rings and cherries really bring it all together for that traditional pineapple upside down cake flavor."

Depending upon how big or small you cut your slices of cake, this recipe serves 10 to 12 people. It's so delicious that there will be nothing left but crumbs scattered on the serving tray. 

Whip up this homemade pineapple upside down bundt cake and splurge on a spectacular slice!

A decadent and rich cake, this recipe requires dark brown sugar, melted butter, a can of pineapple rings, one cup of whole milk, pineapple juice reserved from the canned pineapple rings, maraschino cherries, all-purpose flour, baking powder, salt, unsalted butter, granulated sugar, vanilla extract, and eggs. And if you want to try and convert this to a gluten-free cake, LeAnn says it's possible.

"This cake could definitely be converted to gluten-free very easily. You could replace the all-purpose flour with a good gluten-free flour blend. Usually gluten-free flours will say if you can replace them 1:1 in recipes, so for best results look for that statement on the packaging," LeAnn explains.

First, grease the pan: Use a pastry or basting brush and coat the inside of the bundt cake pan with a ¼ cup of melted butter. Because the bundt cake pan has grooves, be sure to work the butter into those channels.

"I prefer unsalted butter because salt content in butter can vary and change the taste of your baked goods if you use a butter that's too salty," LeAnn explains.

Then measure out ¼ cup of dark brown sugar and sprinkle it all over the inside of the pan. Most of the dark brown sugar will tumble to the lowest part of the pan, which Lee says is just fine. 

Grab some paper towels and prepare to drain and lightly pat dry the fruit.

Drain the can of pineapple and cut each ring in half, making sure to save ¼ cup of the juice to use in the batter. Evenly place the pineapple ring halves around the circular bundt pan, with the curved side down. "They should fit pretty well into the curve of the pan," LeAnn says.

Next, drain 16 maraschino cherries and place one in between each pineapple ring, then set the pan aside.

"It is perfectly fine if the pineapple rings overlap a bit. It's really all about your preference. You could even use more or less pineapple rings and cherries if you wish," she adds.

Preheat the oven to 325 F. In a medium bowl, sift together 3 cups of all-purpose flour, 2 teaspoons baking powder, and a pinch of salt. Set the dry ingredients to the side. 

In the bowl of a stand mixer fitted with the paddle attachment, combine 1 cup of unsalted butter brought to room temperature, 1 ½ cups of granulated sugar, ½ cup of dark brown sugar, and 1 tablespoon of vanilla extract. Whip these ingredients until light and fluffy.

"This can be done with a hand mixer if you don't have a stand mixer," Autumn LeAnn adds.

Once blended, turn the speed of the mixer down and add in one egg at a time, pausing between each egg to allow the butter and sugar mixture to incorporate it properly.

"Adding in one egg at a time allows it to be absorbed by the other ingredients better. If your ingredients don't mix well enough, you will end up with a wonky cake batter that probably won't taste the best," she says.

Scrape down the sides of the bowl with a rubber spatula as needed to make sure everything blends well. Slowly add in half of the flour mixture, then half of the whole milk, and half of the pineapple juice. Mix these ingredients until they are thoroughly combined.

"A plant-based milk alternative could be used in place of whole milk. Using a somewhat creamy consistency option such as coconut cream or oat milk would be ideal," Autumn LeAnn says.

Then add in the other half of the flour mixture, followed by the rest of the whole milk and pineapple juice, making sure to scrape the sides of the bowl each time you add ingredients.

Once the batter is completely blended, pour it evenly and slowly into the prepared bundt cake pan over the pineapple slices and cherries.

"Make sure the batter gets down in between the fruit. You can add some of the batter to a piping bag, or Ziploc bag with a corner cut off, to squeeze the batter in between the fruit if you'd like," Autumn LeAnn advises.

Smooth out the batter with a small icing spatula or butter knife, then lightly but firmly tap the pan on the counter a few times to remove air bubbles.

Bake this beautiful bundt cake for 60 to 75 minutes until completed baked through and through.

"I use the old trick of inserting a toothpick and seeing if it comes out clean to check for doneness," LeAnn notes.

Once the cake is done baking, allow it to cool in the pan for 10 to 15 minutes before carefully removing it.

"You may need to use an icing spatula or butter knife to loosen the cake from the pan before turning the cake out," she says.

Then allow the bundt cake to cool completely before cutting it for the best results, LeAnn suggests.