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A fun twist on the classic cake recipe, these pineapple upside down cupcakes have the perfect hint of pineapple flavor!

These tropical pineapple upside down cupcakes are a great addition to any BBQ or get-together. If you love the classic Pineapple Upside Down Cake, then these individualized treats are sure to be a hit anywhere you take them.

Close up of pineapple upside down cupcakes topped with cherries.

classic Cake in Cupcake Form

Whenever I eat pineapple upside-down cake, it always brings back fond memories of family gatherings. It’s a popular recipe during holidays like Christmas and Easter, but we also love enjoying it during the summer. There’s nothing more refreshing than pineapple flavor

For a fun twist on the classic cake recipe, I decided to try a cupcake version! I couldn’t be more pleased with how they turned out. All the amazing tastes of pineapple-flavored cake, with caramelized pineapple slices and cherries on top, but in individual serving sizes.

Pineapple upside-down cupcakes are just as simpleโ€”if not simplerโ€”to make, and are a crowd-pleaser. Everyone loves them, especially the kids. Plus, are they not adorable?!

Sugar mixture in a glass bowl.

How to Make Pineapple Upside Down Cupcakes

Pineapple upside down cupcakes with cake mix are so simple to make and are delightful tropical.

PREP. Preheat the oven to 350ยฐF. Prepare 24 wells of a muffin tin by spraying with cooking spray.

CAKE. In a large bowl, mix together the pineapple juice, yellow cake mix, oil, and eggs until well blended.

FRUIT. Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.

BAKE. Pour the cake batter into the cupcake tin, filling to about ยผ inch from the top. Bake 20-25 minutes, or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.

Serve warm with freshly Whipped Cream, if desired.

Putting pineapple and cherries in the bottom of a cupcake tin.

Recipe Tips

This pineapple upside down cupcake recipe is pretty magical. The pineapple adds the perfect amount of brightness.

Pineapple. You can cut the rings into smaller sections or buy a 20-ounce can of pineapple chunks or even use crushed pineapple or pineapple tidbits.  

The amount of pineapple juice should equal to 1 cup. If you are shy, add water to the juice to get 1 cup.

Liners. I don’t recommend lining the muffin cups with paper cupcake liners, however, you can use reusable silicone liners. 

Cake mix. The yellow cake mix can be substituted with a pineapple cake mix.

Flipping Tips

Flipping the cupcakes is the hardest part, and even then, it’s not too difficult. Here are some tips to help you flip the cupcakes.

  • Wait a few minutes for the little cakes to cool a bit.
  • Use a sharp paring knife or a small rubber spatula and slide it around each cake releasing the sides from the pan.
  • Flip the cupcake pan onto wax paper.
  • Allow the cupcakes to sit for another few minutes with the pan still covering them.
  • The cakes should begin to plop down on their own. Carefully remove the pan.

Voila – not too hard, right?!

Cupcake batter in a prepped muffin tin.

Storing Info

STORE. Store the pineapple upside down cake cupcakes in the fridge, in an airtight container, for about 3 days.

FREEZE. To store in the freezer, allow the cupcakes to cool and flash freeze by placing them in the freezer for about an hour. Take the cupcakes out, wrap them with plastic wrap, then again with foil.

Or place the wrapped cupcakes in a freezer-safe container. Label and freeze for 2-3 months.ย 

A plate piled with pineapple upside down cupcakes.

Recipe FAQ

How do I keep the pineapple upside down cupcakes from sticking to the pan?

Be sure to remove them before they have a chance to cool off too much. If you wait too long the sugary topping will cool into a sticky syrup which will make it harder to remove the cupcakes successfully. If you wish, you can cut small rounds out of parchment paper to add to the bottom of each cupcake well.

Why are my pineapple upside down cupcakes soggy?

The tops will be sticky but the base should not be soggy. Be sure to use the ingredients listed on the recipe card and do not follow the box directions, drain the pineapple and cherries, and bake until a toothpick inserted into the center comes out clean or with a few moist crumbs.

For More Fruity Cupcake Recipes, Try:

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5 from 51 votes

Pineapple Upside Down Cupcakes Recipe

By: Lil’ Luna
A fun twist on the classic cake recipe, these pineapple upside down cupcakes have the perfect hint of pineapple flavor!
Servings: 24
Prep: 10 minutes
Cook: 20 minutes
Total: 30 minutes

Ingredients 

  • 1 (20-ounce) can pineapple rings drained and juice reserved
  • 1 (15.25-ounce) box yellow cake mix
  • ยฝ cup vegetable oil
  • 3 eggs
  • โ…“ cup butter melted
  • โ…” cup brown sugar packed
  • 12 maraschino cherries cut in half

Instructions 

  • Preheat the oven to 350ยฐF. Prepare 24 wells of a muffin tin by spraying with cooking spray.
  • In a large bowl, mix together the pineapple juice, yellow cake mix, oil, and eggs until well blended.
  • Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.
  • Pour the cake batter into the muffin tins, filling to about ยผ inch from the top. Bake 20-25 minutes or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.
  • Serve warm with freshly whipped cream, if desired.

Video

Nutrition

Calories: 192kcal, Carbohydrates: 28g, Protein: 1g, Fat: 8g, Saturated Fat: 2g, Cholesterol: 27mg, Sodium: 189mg, Potassium: 55mg, Sugar: 19g, Vitamin A: 120IU, Vitamin C: 2.2mg, Calcium: 59mg, Iron: 0.7mg

Nutrition information is automatically calculated, so should only be used as an approximation.

adapted from Betty Crocker

 

About Kristyn

My name is Kristyn and Iโ€™m the mom of SIX stinkinโ€™ cute kids and the wife to my smokinโ€™ hot hubby, Lo. My momโ€™s maiden name is Luna, and Iโ€™m one of the many crafty โ€œLilโ€™ Lunasโ€ in the fam. On this site I like to share all things creative - from recipes to home decor to gifts and home decor ideas. Welcome!

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5 from 51 votes (37 ratings without comment)

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Recipe Rating




31 Comments

  1. Amy L Huntley says:

    5 stars
    I love that these are cupcakes. so BEAUTIFUL and tasty. Making these more this summer.

  2. Becca says:

    5 stars
    SUch a fun twist on a classic. Perfect for parties!

  3. Misty says:

    5 stars
    my daughter made these with her friends the other day! They turned out great!

  4. Joy says:

    5 stars
    My hubby loves these! I am more of the chocolate fan & him the fruity, but I really do like these! They are soft & full of flavor! I love pineapple, so if I can’t have chocolate, this is the next best!

  5. Kristina says:

    5 stars
    Pineapple upside down cake made in a dutch oven is my moms favorite camping treat. With your delicious recipe and instructions im able to have it at home!

  6. Olivia says:

    5 stars
    My husband can eat a whole upside down cake by himself. Excited to try these individual servings. Same great taSte.

  7. Bill Kreeger says:

    These look absolutely fantastic. I made similar cupcakes for a church function last year and they went over very well. I used some crushed pineapple and some which had been cut into quarters (two to a muffin cup). 1/4 tsp butter, one tsp crushed pineapple, 1/2 cherry then fill each cup to about 1/4 inch from top.

    1. Kristyn Merkley says:

      That sounds great! I bet they were a hit ๐Ÿ™‚

      1. Bill Kreeger says:

        Must have been. Iโ€™ve been volunteered to make more this year (+ 3 additional cakes) for their bake sale

  8. Crystal says:

    Super delicious and so cute!! Perfect for a party. Thanks for the recipe!!

    1. Lil' Luna says:

      They’re perfect for parties!! Hope you give them a try:) Let me know what you think!

  9. Roxana says:

    5 stars
    Such cute little cakes!

    1. Lil' Luna says:

      Aren’t they!:) Thanks so much for checking them out!

  10. Liz says:

    Nice recipes Kristyn. Thank you and have a great Monday.