These Pineapple Upside Down Cupcakes are the perfect combination of sweet and tangy, with a moist vanilla cake base topped with caramelized brown sugar and pineapple rings. Not only are they delicious, but they’re also incredibly easy to make!
This tasty recipe is a cupcake version of the famous upside cake recipe. What I love about this recipe is that it gives the perfect individual-sized treats, and they cook so much faster than a traditional cake so you can spend less time in the kitchen.
Table of Contents
Why You’ll Love This Recipe
- The combination of pineapple and brown sugar adds a delicious sweet and tangy taste to these cupcakes.
- Whether it’s a summer BBQ, birthday party, or just a mid-week treat, these cupcakes are sure to be a hit.
- With just a few simple ingredients and minimal prep time, you can whip up these cupcakes in no time.
- Cupcakes are the perfect individual-sized dessert that is easy to transport for potlucks, picnics, or parties.
To make this miniature version of this pineapple upside down cake recipe you will need a few simple ingredients. But, you don’t have to worry about all these ingredients because they are all budget-friendly and easy to find at your local grocery stores, so you don’t have to worry about tracking down anything special.
For the Caramel Topping:
- brown sugar
- maraschino cherries
- pineapple slices
For the Cupcakes:
- all-purpose flour
- leavening agents – baking powder and baking soda. Be sure that these baking essentials have not expired.
- allspice – the perfect addition of earthy spices in this cupcake.
- butter, room temperature
- granulated sugar – feel free to lower the carbs by using a sugar alternative like monk fruit for both the granulated and brown sugar.
- eggs, room temperature
- vanilla extract
- buttermilk –
- pineapple juice reserved from canned pineapple slices
How to Make Pineapple Upside Down Cupcakes
Making these cupcakes is so simple. Just follow the step-by-step instructions here or in the recipe card at the bottom of the post and you will have a delicious recipe to enjoy in no time at all.
Step 1: Heat the oven and prepare your baking pan
Preheat oven to 350° F and grease and line the bottoms of 12 jumbo muffin tins with a parchment paper round.
Step 2: Melt butter and brown sugar
Combine 1/2 cup of butter and brown sugar in a small saucepan over medium heat, once butter has melted, whisk into brown sugar until smooth and lightened in color.
Step 3: Add the melted butter and brown sugar mixture to the muffin cups
Spoon a heaping tablespoon of the brown sugar mixture into the bottom of each muffin tin round.
Step 4: Add the pineapple ring and cherry to muffin pan
Gently push down a pineapple ring into the sugar mixture with the back of a spoon and add a maraschino cherry into the center. Repeat with the remaining muffin tin rounds. Set the muffin tins aside.
Step 5: Mix the dry ingredients
Whisk together the flour, baking powder, allspice and salt. Set aside.
Step 6: Cream the wet ingredients for the cake batter
In the bowl of a stand mixer fitted with the paddle attachment, cream butter until light and fluffy, and then add the sugar. Continue mixing until well incorporated. Add vanilla and the eggs (add the eggs one at a time until the previous egg is fully incorporated before adding the next).
Step 7: Add the dry ingredients to the butter mixture
Add the flour mixture to the bowl of the stand mixer and mix on low speed until the ingredients are fully incorporated.
Step 8: Add the cupcake batter to the bottom of a cupcake pan
Using a large 3-tablespoon cookie scoop, dollop the batter onto the pineapple rings until each muffin cup is two-thirds full. Even out the batter and spread it to the sides using an offset spatula.
Step 9: Bake the cupcakes
Bake in the oven on the middle rack for 20-25 minutes or until the tops appear golden and the cupcake springs back when touched lightly with your finger.
Step 10: Top the cupcakes with pineapple juice
Remove the muffin tins from the oven, place them on a wire cooling rack, and brush the reserved pineapple juice over the tops of each cupcake, letting the juice soak into the cupcake.
Step 11: Cool slightly before removing from the pan
Allow cupcakes to cool for 10-15 minutes before loosening the sides of them with a small sharp knife. Invert onto a serving platter until ready to serve.
Substitutions and Additions
Here are a few ways that you can change up this recipe to suit your tastebuds.
- Instead of making a homemade vanilla cake like I did, you can use a box of vanilla cake mix or even your favorite pineapple cake mix instead. See the recipe card for additional notes on using a cake mix. I recommend giving the homemade a try though, it’s delicious.
- You can also add a splash or two of pineapple juice to your batter to make a moist pineapple cake batter for even more pineapple flavor.
- If you are not a fan of cherries feel free to leave them off.
- If you don’t care for allspice, then you can use ground cinnamon instead.
- For a boozy addition, brush on rum in place of the pineapple juice to give a deep rich flavor.
- If you don’t have allspice on hand you can use the following substitution: 1/2 teaspoon cinnamon, 1/4 teaspoon cloves, 1/4 teaspoon nutmeg.
Storing Pineapple Upside Down Cupcakes
Store – If you manage to have leftover cupcakes, don’t worry you can save them again for another day. Store these cupcakes in an airtight container in the refrigerator for up to 3 days or cover them with plastic wrap. Before serving, let them come to room temperature or heat up in the microwave for a few seconds.
Serve With Pineapple Cupcakes
One great thing about this delicious recipe is that pairs well with just about any meal some of my favorite recipes to pair with them are this Chicken Marsala recipe or this Easy Sheet Pan Roasted Half Chicken. Either one of these recipes will give you a great meal.
Sandra’s Pro Tips
Here are a few tips that you can use to help you make this mini pineapple upside down cake recipe.
- For this recipe, you are not using cupcake liners. To remove the cupcakes with ease, you can use small parchment paper rounds on the bottom of the pan to prevent sticking or spray your muffin tin with nonstick cooking spray. However, I find that the butter and brown sugar mix adds enough grease to the pan.
- Make sure you allow the cupcakes to cool for 10 minutes before removing them from the pan and use a sharp knife around the edge to help loosen them from the pan.
- Make sure that you use pineapple rings and not crushed pineapple or pineapple tidbits. Crushed pineapple will not give the same beautiful toppings for these delicious cupcakes.
- For best results, you will need to use canned pineapple and not fresh pineapple. The fresh pineapple could make your cupcakes too watery on the bottom.
Do you have questions about this classic dessert recipe? Here are the answers to the most commonly asked questions for this pineapple upside down cupcakes recipe.
While you can use fresh pineapple for this recipe, it is not recommended. The high water content in fresh pineapple can make the cupcakes too moist on the bottom and affect the overall texture of the cake.
You can freeze these cupcakes by wrapping them individually in plastic wrap and then storing them in an airtight container or freezer bag. They will last for up to 3 months in the freezer. When ready to eat, let them thaw at room temperature before enjoying.
Yes, instead of using a jumbo-size muffin tin you can use a traditional size tin. However, the pineapple may not fit, so you will need to cut the pineapple or use pieces instead of the whole pineapple ring.
More Cupcake Recipes That You May Enjoy:
- Vanilla fudge filled cupcakes
- Birthday Cupcakes
- Chocolate Cupcakes with Peanut Butter Frosting
- Churro Cupcakes
- For a low-sugar option try these Sugar Free Cupcakes
Pineapple Upside Down Cupcakes From Scratch
- small saucepan
- jumbo muffin tin or cupcake tin
- Mixing bowls
- electric mixer – I used a stand mixer
- Cookie scoop
- 1/2 cup butter
- 1 cup brown sugar loosely packed
- 12 maraschino cherries blotted dry
- 2 15 ounce cans pineapple slices (do not drain)
- 2 1/2 cups all-purpose flour
- 3 teaspoons baking powder
- 1 teaspoon allspice
- 1/2 teaspoon baking soda
- 1/2 teaspoon salt
- 3/4 cup butter room temperature
- 1 1/4 cups granulated sugar
- 3 eggs room temperature
- 2 teaspoons vanilla extract
- 2/3 cup buttermilk
- 1/3 cup juice reserved from canned pineapple slices
- Preheat oven to 350° F and grease and line the bottoms of 12 jumbo muffin tins with a parchment paper round.
- Combine 1/2 cup of butter and brown sugar in a small saucepan over medium heat, once butter has melted, whisk into brown sugar until smooth and lightened in color.
- Spoon a heaping tablespoon of the brown sugar mixture into the bottom of each muffin tin round
- Gently push a pineapple ring into the sugar mixture and add a cherry into the center. Repeat with the remaining muffin tin rounds. Set the muffin tins aside.
- Whisk together the flour, baking powder, allspice and salt. Set aside.
- In the bowl of a stand mixer fitted with the paddle attachment, cream butter until light and fluffy, and then add the sugar. Continue mixing until well incorporated.
- Add vanilla and the eggs (add the eggs one at a time until the previous egg is fully incorporated before adding next)
- Add the flour mixture to the bowl of the stand mixer and mix on low speed until the ingredients are fully incorporated.
- Using a large 3-tablespoon cookie scoop, dollop the batter onto the pineapple rings until each muffin cup is two-thirds full. Even out the batter and spread it to the sides using an offset spatula
- Bake in the oven on the middle rack for 20-25 minutes or until the tops appear golden and the cupcake springs back when touched lightly with your finger.
- Remove the muffin tins from the oven, place them on a wire cooling rack, and brush the reserved pineapple juice over the tops of each cupcake, letting the juice soak into the cupcake.
- Allow cupcakes to cool for 10-15 minutes before loosening the sides of them with a small sharp knife. Invert onto a serving platter until ready to serve.
- This recipe will produce a dense cake (not the light and airy cakes you may find in layer cakes). If you want a light and airy version, you can opt to use a boxed cake mix, but note that it may not hold up to the heaviness of the pineapple and brown sugar topping.
- Make sure to blot the pineapples to remove excess moisture as too much wetness will make for a soggy cupcake that won’t bake properly.
- As hard as it is to wait, it is important to let the cupcakes sit for 10-15 minutes before inverting them onto the plate, the topping has to “set” as much as it can so that it comes out easily and attached to the cupcake.
- A 15-ounce can of pineapple slices contains about 8 slices, and a 20-ounce can contains about 10 slices
Please note that the nutritional information provided are guidelines and may vary based on the brand of products used. For your specific nutritional goals use My Fitness Pal or Verywell Fit recipe calculators. All content within this site is not intended as medical diagnosis or treatment and should not be considered a substitute for professional medical expertise.