These Pineapple Upside Down Cupcakes are a fun twist on the classic dessert! The soft and fluffy vanilla cupcakes are topped with juicy pineapple slices and sweet maraschino cherries, all coated in a delicious caramelized brown sugar glaze. Not only do they look beautiful, but they taste incredible!

Pineapple upside down cupcakes on a white oval plate.
You can top these with whipped cream if you want!

These Pineapple upside down cupcakes are just like a classic pineapple upside down cake but made into individual servings! Don’t be intimidated by the recipe, it’s actually super simple to make and it has that wow factor when you flip the cupcakes over revealing the pretty pineapple and cherry design.

As a trained pastry chef, I have made many homemade cupcake recipes, but not many that have a built in design like these. To make these cupcakes you’ll pour a brown sugar glaze on the bottom of the muffin tin, then top with pineapple and cherry. Then you’ll pour the batter in, bake and flip!

Out will come a moist and flavorful pineapple upside down cupcake. After they cool you can top them with a chantilly cream, or just leave them plain. They are delicious either way!

You can also make a pineapple upside down bundt cake and impress all your guests! They dont have to know how easy it truly is.

If tropical flavors are your thing then try out these coconut cupcakes, or this coconut frosting.

WHY YOU SHOULD MAKE THIS RECIPE

  • These cupcakes look impressive but are really easy to make!
  • They are perfect to bring to any bbq or potluck.
  • The cupcake is super moist and has a tropical fruit flavor!

INGREDIENTS NEEDED

Ingredients for pineapple upside down cupcakes.
All you need for Pineapple upside down cupcakes.
  • Canned Pineapple (slices or pieces) – The canned pineapple is a key ingredient in this recipe, adding a sweet and tangy flavor to the cupcakes. If you are using the slices you will need two cans.
  • Unsalted Butter – Gets melted and combined with brown sugar to create a caramel-like glaze that is poured into the bottom of the muffin tin before adding the pineapple and cherry. The butter also helps to keep the cupcakes moist and adds richness to the batter.
  • Sugar – Brown sugar is combined with melted butter to create a caramel-like glaze that is poured into the bottom of the muffin tin. The white sugar is combined with the dry ingredients to add sweetness to the cupcakes.
  • Maraschino Cherries – Get placed on top of the pineapple slices or pieces and add a pop of color to the cupcakes. They also add a sweet flavor that complements the tanginess of the pineapple.
  • Flour – The main dry ingredient in the cupcake batter and provides structure to the cupcakes.
  • Leavening Agents – Baking soda and baking powder help the cupcakes rise and become fluffy.
  • Kosher Salt – Enhances the flavors of the cupcakes and balances out the sweetness.
  • Pineapple Juice – Reserved pineapple juice is added to the cupcake batter and helps to keep the cupcakes moist and tender. It also adds a subtle pineapple flavor to the base cupcakes.
  • Vegetable Oil – Adds moisture to the cupcakes and helps keep them soft and tender.
  • Egg – Acts as a binding agent in the cupcake batter and helps to hold everything together.
  • Vanilla Extract – Adds a subtle vanilla flavor to the cupcakes. It also enhances the sweetness of the cupcakes and helps to balance out the flavors.

Using Pineapple Rings or pieces

It’s easiest to use canned pineapple for this recipe. You can use either pineapple rings/slices or already cut pieces or chunks.

Some cupcake tins are not big enough to fit the pineapple slices. If yours isn’t, use the pieces instead. If they are really chunky or large pieces, cut them in half. 

HOW TO MAKE PINEAPPLE UPSIDE DOWN CUPCAKES

Prepare for baking: Preheat the oven to 350° F and spray a muffin tin with baking spray- preferably one made with flour.

Drain the canned pineapple: Drain the canned pineapple, reserving ¾ cup of juice. Dry the pineapple slices or pieces well.

Assemble the brown sugar glaze: In a small pot, add the unsalted butter and brown sugar and melt over low- medium heat. Add 1 tbsp of the brown sugar mixture to the bottom of each muffin tin.

Add pineapples and cherry: Add one pineapple ring, then add a maraschino cherry on top of the brown sugar mixture. If you are using pieces, place 3-4 slices around the tin with the cherry in the middle.

Combine the dry ingredients: In a large mixing bowl, combine the sugar, all-purpose flour, baking powder, baking soda, and kosher salt and whisk lightly to combine.

Add wet ingredients: Add in the ¾ cup reserved pineapple juice, vegetable oil, egg, and vanilla extract if using. Mix until combined but do not overmix.

Fill, bake, and cool: Fill each cup ⅔ of the way full. Do not overfill. You may have a small amount of batter left over. Bake for 18 minutes. Cool for 10 minutes in the pan, then use a knife to go around the edges of each muffin tin

Remove the cupcakes: Set a wire rack over a parchment-covered sheet tray. Invert the cupcakes onto the wire rack and let them cool completely. Top with whipped cream or powdered sugar for garnish. Enjoy!

Pineapple chunks on a paper towel.
Use Pineapple chunks or cut pineapple rings.
Sugar glaze in a pot.
This brown sugar glaze is super easy to make.
Glaze in a muffin tin.
You only need a small amount in the muffin tin.
Pineapple pieces and cherries in the bottom of a muffin tin.
Add 3-4 pineapple chunks with a cherry in the center.
Dry ingredients in a glass bowl on a yellow surface.
Combine the dry ingredients.
Wet ingredients in a glass bowl on a yellow surface.
Make the cupcake batter.
Cupcake batter in a muffin tin.
Pour the cupcake batter on top of the pineapple and cherries.
Pineapple upside down cupcakes in a muffin tin.
Don’t be afraid to flip them!

TIPS FOR RECIPE SUCCESS

  • Drain the canned pineapple slices or pieces thoroughly and pat them dry with a paper towel. This will prevent the cupcakes from becoming too moist and soggy.
  • Be careful not to overfill the muffin tins with batter. Fill each tin about two-thirds of the way full to ensure the cupcakes rise evenly and don’t overflow.
  • To prevent the cupcakes from sticking to the muffin tin, be sure to use a baking spray that contains flour or butter and flour. You can also use cupcake liners if you prefer.
  • When making the brown sugar glaze, make sure to melt the butter and brown sugar over low-medium heat. If the heat is too high, the mixture can burn and become bitter.
  • Allow the cupcakes to cool for at least 10 minutes in the pan before removing them. This will give the brown sugar glaze time to set and prevent the cupcakes from falling apart when you remove them from the pan.

STORAGE AND FREEZING

Storing: Store in an airtight container at room temperature for up to 3 days. If you want to keep them fresh for longer, you can store them in the refrigerator for up to 5 days. To maintain their freshness, store them in a container with a tight-fitting lid.

Freezing: These cupcakes can be frozen for up to 3 months. Freeze each cupcake individually in plastic wrap and then place them in a freezer-safe container or freezer bag. When you’re ready to eat them, remove them from the freezer and let them thaw at room temperature for a few hours before serving.

Pineapple upside down cupcakes on a wire rack.
The cupcakes will easily slide out of the muffin tin.

FAQ

Why is my pineapple upside down cake soggy?

There are several possible reasons why your cupcakes may be soggy. It could be because you didn’t drain the canned pineapple properly, there was too much liquid in the batter or you overfilled the muffin tin with batter. All of these can cause a soggy texture and tastelessness.

Can I use fresh pineapple instead?

Yes, you can use fresh pineapple for this recipe. Start by slicing the pineapple into rings or chunks and pat them dry with a paper towel to remove any excess moisture. You’ll also need to reduce the amount of juice in the batter since fresh pineapples contain more liquid than canned pineapples.

MORE FRUITY CUPCAKE RECIPES

Pineapple upside down cupcakes on a wire rack.
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From Scratch Pineapple Upside Down Cupcakes

These Pineapple Upside Down Cupcakes are a fun twist on the classic dessert! The soft and fluffy vanilla cupcakes are topped with juicy pineapple slices and sweet maraschino cherries, all coated in a delicious caramelized brown sugar glaze. Not only do they look beautiful, but they taste incredible!

Ingredients

  • 20 oz pineapple slices, canned, or pieces (if using slices you need 2 cans)
  • ½ cup unsalted butter
  • ¾ cup brown sugar
  • Maraschino cherries, 1 jar
  • 1 ¼ cup flour, 160g
  • ¾ cup granulated sugar, 150g
  • 1 tsp baking powder
  • ¼ tsp baking soda
  • ½ tsp kosher salt
  • ¾ cup pineapple juice
  • ¼ cup vegetable oil
  • 1 egg
  • 2 tsp vanilla extract, (optional)

Instructions
 

  • Preheat the oven to 350° F and spray a muffin tin with baking spray- preferably one that is made with flour.
  • Pineapple chunks on a paper towel.
    Drain the pineapple can, reserving ¾ cup of juice. Dry the pineapple slices or pieces well.
  • Sugar glaze in a pot.
    In a small pot add the ½ cup unsalted butter and ¾ cup brown sugar and melt over low- medium heat.
  • Glaze in a muffin tin.
    Add 1 tbsp of the brown sugar mixture to the bottom of each muffin tin.
  • If using pineapple slices/rings- add one to the bottom of your muffin tin with a cherry in the middle. My muffin tin was too small for the ring to fit nicely so I cut it into chunks.
  • Pineapple pieces and cherries in the bottom of a muffin tin.
    If using chunks/pieces– use 3-4 pieces around the muffin tin and place a cherry in the center. If they are very chunky slice them in half.
  • Dry ingredients in a glass bowl on a yellow surface.
    In a large mixing bowl combine the 1 ¼ cup all purpose flour, ¾ cup sugar,1 tsp baking powder, ¼ tsp baking soda, and ½ tsp kosher salt and whisk lightly to combine.
  • Wet ingredients in a glass bowl on a yellow surface.
    Next add in the ¾ reserved pineapple juice, 1/4 cup vegetable oil, 1 egg, and 2 tsp vanilla extract if using. Mix until combined but do not over mix.
  • Cupcake batter in a muffin tin.
    Fill each cup ⅔ of the way full. Do not overfill. You may have a small amount of batter left over. Bake for 18 minutes.
  • Pineapple upside down cupcakes in a muffin tin.
    Cool for 10 minutes in the pan then use a knife to go around the edges of each muffin tin.
  • Pineapple upside down cupcakes on a wire rack.
    Set a wire rack over a parchment covered sheet tray and invert the cupcakes onto the wire rack and let cool completely.
  • Top with whipped cream or powdered sugar for garnish (optional).

Notes

You can use pineapple slices or chunks. Some muffin tins are too small to fit the whole slice nicely so you can cut them up or just use chunks instead.
Serving: 1cupcake, Calories: 300kcal, Carbohydrates: 46g, Protein: 2g, Fat: 13g, Saturated Fat: 6g, Polyunsaturated Fat: 3g, Monounsaturated Fat: 3g, Trans Fat: 0.3g, Cholesterol: 34mg, Sodium: 166mg, Potassium: 119mg, Fiber: 1g, Sugar: 34g, Vitamin A: 281IU, Vitamin C: 6mg, Calcium: 47mg, Iron: 1mg
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