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Why You Will Love This Pineapple Cherry Upside-Down Pound Cake
Pound cakes may not have originated in the South, but the South has definitely made them our own! Growing up, I remember pound cake being one a dessert I would always look forward to, especially around the holidays. There’s just something about a soft, sweet slice of pound cake that feels like home.
This Pineapple Cherry Upside-Down Pound Cake is made with a buttery, fluffy pound cake batter filled with pineapple tidbits and cherries. It’s baked over a layer of melted butter, brown sugar, and fruit, then flipped to reveal a beautiful, colorful topping. And because a little homemade icing never hurt anybody, we’re finishing it off with a simple vanilla icing drizzled right over the top.
Ingredients
- Pineapple tidbits and pitted cherries: I use frozen fruit, thawed and drained. You’ll divide the fruit between the cake batter and the bottom of the Bundt pan.
- Butter and cream cheese: Room-temperature butter and cream cheese add richness and give the pound cake its buttery texture. You’ll also need a little melted butter for the pan.
- Granulated and brown sugar: Granulated sugar sweetens the cake, while brown sugar creates a sweet glaze underneath the fruit.
- Eggs: Five large eggs help bind the batter and give the cake structure.
- All-purpose flour, baking powder, and salt: These dry ingredients form the base of the cake.
- Milk: Helps bring the batter together and gives it a smooth consistency.
- Vanilla extract: Adds flavor to both the cake and homemade icing.
- Powdered sugar and heavy whipping cream: These come together with vanilla to make a simple icing to drizzle over the finished cake.

How to Make Pineapple Cherry Upside-Down Pound Cake
Start by sifting together the all-purpose flour, baking powder, and salt. Set the dry ingredients aside.

Add the room-temperature butter and granulated sugar to your stand mixer. Mix until everything comes together. Add the room-temperature cream cheese and continue mixing.


While the mixer is running, add the eggs one at a time, allowing each egg to incorporate into the batter.

Next, add some of the drained pineapple tidbits and cherries. Be sure to reserve enough fruit for the bottom of your Bundt pan.

Now it’s time to add the flour mixture and milk. Slowly add the flour in batches, alternating with small amounts of milk. Start with some flour, add a little milk, and continue alternating until both are incorporated.


Let the batter mix until everything comes together. Next, add ½ teaspoon vanilla extract and mix until combined. You want a fluffy, thick batter with a little weight to it, almost like a thick pancake batter. It should not be runny.

Prepare the Bundt Pan
Pour the melted butter into the bottom of your Bundt pan. Sprinkle the brown sugar over the butter, spreading it out to cover the bottom.


Add the remaining pineapple tidbits and cherries over the brown sugar. Spread the fruit around so you’ll have a beautiful topping once the cake is flipped.

Fill the Pan and Bake
Using an ice cream scoop, transfer the cake batter into the Bundt pan. I like using an ice cream scoop because it makes it easy to distribute the batter evenly.

Continue adding batter until the pan is filled, but be careful not to overfill it. Leave some room at the top for the cake to rise. Smooth the top with a spoon.

Bake at 350°F for approximately 1 hour. To check if the cake is done, insert a fork or toothpick into the center. It should come out clean or with just a few crumbs.


A note about extra batter: Depending on the size of your Bundt pan, you may have some batter left over. I had enough for an additional smaller cake! Just be sure to use a separate, appropriately sized baking pan and avoid overfilling either pan.
Cool and Flip the Cake
Remove the cake from the oven and let it cool down some before flipping it out of the pan.

Carefully flip the Bundt pan onto your serving plate or cake stand and lift the pan away. You should be left with a beautiful layer of pineapple and cherries sitting on top of the cake!
Make the Homemade Icing
In a small bowl, combine the powdered sugar, heavy whipping cream, and vanilla extract. Mix until smooth. Drizzle the icing over the cake and enjoy!

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Tips for the Best Pineapple Cherry Upside-Down Pound Cake
- Use room-temperature ingredients: Let your butter, cream cheese, and eggs come to room temperature before mixing. This helps everything blend together smoothly.
- Don’t overfill your Bundt pan: Leave room for the cake to rise. If you have extra batter, bake it separately in a smaller pan.
Other Recipes You Will Love
If you loved this, you have to try my Lemon Bundt Cake!
Pineapple Cherry Upside-Down Pound Cake
Description
This Pineapple Cherry Upside-Down Pound Cake is soft, buttery, and filled with pineapple and cherries. Topped with a brown sugar glaze and homemade icing, it's perfect for the holidays!
Ingredients
Cake Batter
Pan Toppings
Homemade Icing
Instructions
-
Sift together the flour, baking powder, and salt.
-
In a stand mixer, cream together the room-temperature butter and granulated sugar. Add the cream cheese and mix until combined.
-
Add the eggs one at a time.
-
Add some of the pineapple and cherries to the batter, reserving the remaining fruit for the pan topping.
-
Slowly add the flour mixture in batches, alternating with the milk until everything is incorporated.
-
Add in the vanilla extract. Mix until the batter is fluffy.
-
Pour the melted butter into the bottom of a Bundt pan. Sprinkle the brown sugar over the butter.
-
Arrange the leftover pineapple and cherries on top.
-
Scoop the cake batter into the pan, leaving room at the top for the cake to rise.
-
Bake at 350°F for approximately 1 hour, or until a fork or toothpick inserted into the cake comes out clean.
-
Remove the cake from the oven and let it cool to for about 20 minutes.
-
Carefully flip it onto a serving plate.
-
Drizzle the icing over the cooled cake before serving.
Nutrition Facts
Servings 12
- Amount Per Serving
- Calories 656kcal
- % Daily Value *
- Total Fat 29g45%
- Saturated Fat 18g90%
- Sodium 486mg21%
- Total Carbohydrate 95g32%
- Dietary Fiber 2g8%
- Sugars 69g
- Protein 7g15%
* Percent Daily Values are based on a 2,000 calorie diet. Your daily value may be higher or lower depending on your calorie needs.

