Upside Down Pineapple Loaf Cake

Upside Down Pineapple Cake is a definite crowd pleaser with its sweet, caramelized pineapple and cherry topping that compliments its vanilla cake. This Upside Down Pineapple Loaf Cake has all of the qualities of the classic, but as a loaf cake so it's perfect for a smaller crowd.

I love how fancy Upside Down Pineapple Cake looks, but that it's actually really easy to make. That beautiful topping is a combination of some melted butter, brown sugar, pineapple rings and maraschino cherries and it always comes out looking amazing.

A FEW NOTES BEFORE WE GET STARTED

• Room Temperature Ingredients:
  • Butter: It’s important that your butter is softened. In a pinch, you can put your butter in the microwave for about 5 seconds on each side, but watch closely to make sure it is just softening and not melting.
  • Eggs: You also want to make sure that the eggs are at room temperature to ensure that they are properly incorporated into your batter. If you forget to leave them out before you start baking, place them in a bowl of warm water for about 15 minutes until they become room temperature.
• Measuring Your Ingredients: I strongly encourage that you use a kitchen scale to measure your ingredients and ensure that you have the most accurate measurements possible.
  • However, if you don’t have a scale on hand and will be using cup measurements, make sure to use the “spoon and sweep” method when measuring to avoid packing in too much of any dry ingredient.
• Oven Temperature: Make sure to preheat your oven for at least 15 minutes before you start baking.
  • I recommend purchasing an oven thermometer to get to know your oven so you can adjust your baking temperatures accordingly. Some ovens run slightly warmer or colder so its important to know yours to make sure your baked goods come out right.
• Check out My Favorite Baking Tools to see what I use when I bake.

Now let's bake! Preheat your oven to 350 F. Prep a 1 lb loaf pan by coating it with cooking spray and lining it with parchment that slightly overhangs on each side. Do not skip this step.

Pour melted butter into the pan and move the pan around so it evenly coats the bottom. Add brown sugar and spread out evenly over the butter.

Put the pineapple rings on a paper towel and top with another paper towel. Gently press down to squeeze out any excess liquid. Repeat this a few times until they are no longer letting out liquid. Do this same process with the maraschino cherries.

Place one pineapple ring in the center of the pan on top of the brown sugar. Cut the other ring in half and place each half on either side of the middle ring, with the cut side facing the sides of the pan. 

Place a maraschino cherry in each pineapple ring hole. Chill the pan until you are ready to use it.

In a stand mixer fitted with a paddle attachment, combine the butter and sugar for 2-3 minutes on medium speed until light and fluffy. Add eggs, one at a time, scraping down the sides of the bowl with your spatula as needed. Add vanilla.

Add the flour, baking powder, and salt followed by the milk and pineapple juice. Mix on low just until combined and scrape down the sides of the bowl as needed.

Carefully pour the batter into the prepared pan and use an offset spatula to spread it evenly over the pineapple topping. Bake the loaf for 45-50 minutes until a toothpick or knife inserted into the center comes out clean.

Cool for 30 minutes on a cooling rack before gently running a knife along the edges and carefully using the overhanging parchment to lift the cake out of the pan. Enjoy!