There's something about this pineapple upside-down cаke that just feels magical , you know ? It started popping up in kitchens back in the early 1900s when canned pineapple was the new big thing . Folks loved how that brown sugar and butter mix would seep into the soft cаke for a sweet and tangy bite . Today it's still a favorite at potlucks , birthdays and family dinners .
Thіs version stands out as the best pineapple upside-down cake for real . It mixes juісy pineapple rings with gooey brown sugar , a touch of bright cherries , and a soft cake that literally melts in your mouth . Even if you're not super good at baking it’ll still turn out great thanks to simple steps and clear tips . Let’s go over how you can nail this classic treat and make everyone’s eyes light up .

What You Will Learn
In this article you’ll find out what makes this cake so awesome , like how to get that perfect gooey top and a cake that’s light and fluffy . We also give you step by step directions so anyоne from a first time baker to a kitchen pro can follow along without stress .
Ingredients: What You Need for the Best Pineapple Upside-Down Cake
To get this perfect pineapple upside-down cake , you gotta have the right stuff . Here’s what you need for the topping and for the cake batter .
- For the Topping:
- ¼ cup unsalted butter
- 1 cup brown sugar
- Slices of pineapple (fresh or canned)
- Maraschino cherries
- For the Cake:
- 1 ½ cups all purpose flour
- 1 cup granulated sugar
- ½ cup unsalted butter (softened)
- 2 large eggs
- ½ cup milk
- 1 tablespoon baking powder
- 1 teaspoon vanilla extract
- ½ teaspoon salt

Directions: Step-by-Step Recipe
Making this cake is pretty simple , just follow these steps and you’ll have a dessert that looks and tastes like you spent hours on it .
- Prepare the Topping:
First melt ¼ cup of unsalted butter in a small pan over low heat . Then stir in 1 cup brown sugar until it’s all mixed . Pour that into a 9 inch round pan and spread it out . Next place the pineapple slices over the sugar mix , and drop a cherry in the center of each slice .
- Make the Cake Batter:
In another bowl cream together ½ cup softened butter and 1 cup sugar until it’s fluffy . Beat in 2 eggs one at a time , mix well after each , then add 1 teaspoon vanilla . In a different bowl whisk 1 ½ cups all purpose flour with 1 tablespoon baking powder and ½ teaspoon salt . Now add the dry stuff to the wet mix a bit at a time , alternating with ½ cup milk , until the batter is smooth .
- Combine and Bake:
Slowly pour the batter over the pineapple topping , make sure it covers everything evenly . Bake at 350°F (175°C) for 30–35 mins or until a toothpick comes out clean .
- Cool and Flip:
Let it cool for 5–10 mins after you take it out of the oven . Then put a plate on top and flip it over , tap the pan gently so the cake releases . Serve warm or let it cool to room temp .
Tips for the Perfect Pineapple Upside-Down Cake
- Use fresh pineapple if you want stronger flavor , but canned works every time .
- Dark brown sugar gives a deeper taste than light brown .
- Make sure butter , eggs , and milk are at room temp so the batter mixes better .
- Light colored pans bake more even , dark pans can make it too brown .
- To reheat leftovers just zap a slice in the microwave or warm it in the oven .

The Best Pineapple Upside-Down Cake
Equipment
- 1 9-inch round cake pan
- 1 mixing bowls
- 1 electric mixer or whisk
- 1 spatula
- 1 measuring cups and spoons
- 1 toothpick for testing doneness
Ingredients
- ½ cup unsalted butter, softened
- ¾ cup packed brown sugar
- 1 can (20 oz) sliced pineapple, drained and juice reserved
- 8 pieces maraschino cherries
- 1 cup all-purpose flour
- 1 cup granulated sugar
- 2 large eggs
- ½ cup reserved pineapple juice
- 1 ½ teaspoon baking powder
- ½ teaspoon vanilla extract
- ¼ teaspoon salt
Instructions
- Preheat your oven to 350°F (175°C). Grease the 9-inch round cake pan with butter and sprinkle the bottom evenly with brown sugar.
- Arrange the pineapple slices on top of the brown sugar, placing cherries in the center of each slice.
- In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy using an electric mixer or whisk.
- Add the eggs one at a time, mixing well after each addition, then stir in the pineapple juice and vanilla extract.
- In a separate bowl, combine the flour, baking powder, and salt. Gradually add this dry mixture to the wet ingredients, mixing until just combined.
- Pour the cake batter over the pineapple and cherries in the pan, spreading it evenly.
- Bake in the preheated oven for 40-45 minutes, or until a toothpick inserted into the center comes out clean.
- Remove the cake from the oven and let it cool in the pan for about 10 minutes. Then, carefully invert the cake onto a serving platter while it's still warm.




