Mile High Pineapple Upside Down Pound Cake

Go big with this Mile High Pineapple Upside Down Pound Cake! It’s sweet, buttery and packed with flavor!

There’s something timeless about a pineapple upside down cake—but we’re taking it up a notch with this Mile High Pineapple Upside Down Pound Cake. Imagine sinking your teeth into this tall, rich, buttery pound cake decorated with caramelized pineapple rings and cherries, baked right into this cake.

This cake is moist, dense, and bursting with tropical flavor in every bite. Now don't be like me and forget to add the cherries lol. I still think it came out beautifully without them don't you think?

More Pound Cake recipes ---> Pineapple Upside Down Pound Cake, Sour Cream Pound Cake 3.0, Sour Cream Pound Cake 2.0, Sour Cream Pound Cake, Pineapple Pound Cake, German Chocolate Pound Cake, Mile High Oreo Pound Cake, Mile High Sweet Potato Pound Cake with a Bourbon Caramel Glaze

Recommended tools and equipment:

• Mile High Bundt Pan (this pan is needed for this volume of recipe)
• Stand Mixer or Hand Mixer
• Silicone Spatula
• Oven Thermometer
• Cake Keeper
• Measuring Cups and Measuring Spoons

Steps to make the Pound Cake:

Preheat your oven to 325 degrees. Combine the flour and baking powder and sit it to the side.

*You can use all All Purpose flour, all Cake flour or a combination of the two.

Using a hand or stand mixer, mix the butter and sugar on low speed until light and fluffy (approximately 5 minutes). Then add the Pineapple extract or emulsion and mix.

*You can use salted butter instead of unsalted butter and eliminate the salt.

Add the eggs to the bowl one at a time, mixing well after each addition before adding the next egg.

Mix in the flour mixture 1 c at a time alternating with the buttermilk beginning and ending with the flour mixture. 

In a bowl, mix together your brown sugar, melted butter, and pineapple juice.

*May use salted butter instead.

Spray a 18-cup bundt pan with baking spray. Then pour the mixture into the bottom of your prepared pan.

Add your pineapple rings around the bottom and sides of the pan and place a cherry in the center of each pineapple ring.

Pour the batter into the pan and spread it evenly.

Place the cake in the oven and bake for about an hour and 30 minutes. (Bake it longer if needed). The cake is done once an inserted toothpick comes out clean.

Remove the cake from the oven and allow it to cool for about 10-15 minutes before removing it from the pan. Allow the cake to cool before serving.

Helpful Guides for Beginners:

If you're new to baking I got you covered! Here are some helpful guides to help you along the way!

• How to make a moist Pound Cake
• Pound Cake Essential Tools
• Mistakes to avoid when baking a pound cake
• How to prepare Pound Cake ingredients
• How to Make a Pound Cake for Beginners

Pound Cake Tips + Tricks

Whether you are a beginner or have been in the baking game for a while, I hope these tips are helpful in making sure that your pound cake comes out great!

⇢ Properly measure your ingredients – Always measure each ingredient before adding it to the cake to make sure that you have the accurate amount of each ingredient for the recipe. Baking requires exact measurements for the cake to come out correctly. 

⇢ Always use room temperature ingredients – Standard pound cake ingredients include butter and eggs which should always be a room temperature to ensure that they properly blend into the batter and do not cause any clumping. Other common ingredients such as milk, cream cheese, etc should also be a room temperature. Make sure to allow enough time before baking to remove the ingredients from the refrigerator and sit them on the counter to allow them to come to room temperature. 

⇢ Properly cream the butter and sugar together– Once blended the texture should be light and fluffy. Blend the ingredients together at a moderate speed for a least two to three minutes.

⇢ Add the eggs one at a time– Eggs must be added one at a time blending well after each addition. Once you’ve added an egg to the batter and no longer see any yellow, then you can add another egg to the batter.

⇢  Don’t overmix your batter–  Aside from creaming the butter and sugar together, once done adding an ingredient, immediately start adding the next ingredient. If you are not quite ready, stop the mixer until you're ready to add the next ingredient. After you have added the last ingredient, just mix until blended. If the batter still requires mixing, for example, if there is any unmixed batter on the side of the bowl, finish the mixing process using a spoon. 

⇢ Spray the hell out of your bundt pan - My favorite method is using a baking spray such as Baker’s Joy which includes the flour and oil all in one can. It's always a no-fail method for me and the cake comes right out of the pan. You can also grease the pan with oil (solid or liquid) then dust the pan evenly with flour if you prefer that method.

Frequently Asked Questions: