Pineapple Upside Down Cake Pops

Highlighted under: Cozy Dessert Classics

I absolutely adore making Pineapple Upside Down Cake Pops! They combine the flavors of my favorite classic dessert with a fun, bite-sized twist. Each pop packs a delightful burst of juicy pineapple and the rich taste of buttery cake, all coated in a sweet glaze. They’re perfect for parties or just as a sweet treat at home. In just a few simple steps, you can impress your family and friends with these delicious little delights that are sure to become a hit!

Ella

Created by

Ella

Last updated on 2026-02-04T16:53:28.662Z

When I first tried making Pineapple Upside Down Cake Pops, I was amazed at how well the flavors translated into this fun format. The caramelized pineapple pieces retain their sweetness and juiciness, while the cake stays moist and flavorful. My secret is to let the pops chill in the freezer for a bit before serving, which helps the coating set perfectly.

I remember experimenting with different glazes and finally settled on a light orange and vanilla drizzle that complements the pineapple beautifully. It adds a zesty kick that elevates the pops to a whole new level. Trust me, these treats will become a staple at our gatherings!

Why You Will Love This Recipe

  • A fun and trendy twist on the classic dessert
  • Perfectly caramelized pineapple in every bite
  • Moist, flavorful cake that pairs beautifully with glaze

Perfecting the Caramelized Pineapple

The caramelization of the pineapple is a key component that elevates the flavor of these cake pops. Cooking the pineapple with brown sugar and butter over medium heat not only draws out the juices but also helps enhance its natural sweetness. Look for a golden-brown color and slightly softened texture before removing it from the heat—this usually takes about five minutes. This step is crucial as it creates that delightful contrast between the moist cake and the sweet, tangy topping.

If you find that your pineapple doesn't caramelize properly, it could be due to the heat being too low or the pineapple being too watery. In these cases, try cooking it on medium-high for a few more minutes, or drain any excess juice before adding it to the skillet. A well-caramelized pineapple will not only taste good but also add beautiful texture that complements the creamy cake.

Achieving the Perfect Cake Texture

When making the cake batter, it's essential to cream the butter and sugar thoroughly. This aeration process helps create a light and fluffy texture, which is ideal for cake pops. After adding the eggs, mix just until combined; over-mixing at this stage can lead to denser cake pops. The final batter should be smooth but still thick enough to hold the chunks of caramelized pineapple without collapsing or becoming overly crumbly.

Remember to check your baking dish for non-stick properties before pouring in the batter. Greasing is important to ensure easy removal after baking. If you don’t have cooking spray, lining the dish with parchment paper is an excellent alternative, as it provides an additional layer of safety against sticking.

Storage Tips for Cake Pops

After you've assembled your cake pops, you might want to prepare ahead for future occasions. These pops can be stored in an airtight container in the refrigerator for up to a week. Alternatively, if you want to keep them longer, consider freezing them. Place the pops on a baking sheet without touching to freeze individually, then transfer them into a freezer bag for up to 2 months. Thaw in the refrigerator when you’re ready to serve—this helps retain moisture.

For a beautiful presentation, consider drizzling some extra glaze over the pops after they've set. This not only enhances the look but adds an extra layer of flavor. If you're feeling adventurous, try rolling some of the pops in crushed nuts or shredded coconut immediately after dipping for a delicious twist on the classic treat.

Ingredients

For the Cake Pops

  • 1 cup all-purpose flour
  • 1/2 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 2 eggs
  • 1/4 cup milk
  • 1 teaspoon vanilla extract
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt

For the Topping

  • 1 cup pineapple, chopped
  • 1/4 cup brown sugar
  • 1 tablespoon butter

For the Glaze

  • 1/2 cup powdered sugar
  • 1 tablespoon orange juice
  • 1/2 teaspoon vanilla extract

Instructions

Prepare the Topping

In a skillet over medium heat, melt the butter. Add the chopped pineapple and brown sugar, cooking until the pineapple is caramelized, about 5 minutes. Set aside to cool.

Make the Cake Batter

In a mixing bowl, cream together the softened butter and sugar. Add the eggs one at a time, beating well after each addition. Mix in the milk and vanilla extract. Gradually add flour, baking powder, and salt, stirring until combined.

Combine and Bake

Fold the caramelized pineapple into the cake batter. Pour the batter into a greased baking dish and bake at 350°F (175°C) for 25 minutes or until a toothpick inserted in the center comes out clean.

Shape Into Pops

Once cooled, crumble the cake into a large bowl. Roll the crumbled cake into balls and insert a lollipop stick into each. Freeze for at least 30 minutes.

Prepare the Glaze

In a small bowl, whisk together powdered sugar, orange juice, and vanilla extract until smooth.

Dip and Serve

Dip each cake pop into the glaze and allow excess to drip off. Place on a baking sheet lined with parchment paper and let set. Serve chilled.

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Pro Tips

  • For best results, ensure the cake pops are thoroughly chilled before dipping to avoid them falling apart in the glaze.

Ingredient Substitutions

If you want to make a gluten-free version of these pineapple upside down cake pops, substituting all-purpose flour with a 1:1 gluten-free baking blend can work wonders. Ensure that the blend contains xanthan gum, or add it separately to help bind the ingredients together. The flavor will remain intact, and the texture will still be satisfying.

For those butter-intolerant individuals, you can substitute the unsalted butter with a non-dairy option such as coconut oil or a vegan butter alternative. Just make sure that your chosen substitute has a similar fat content to maintain the moisture level in the batter.

Variations to Explore

Feel free to switch up the flavors of your cake pops! For an added twist, consider incorporating spices into the batter, like cinnamon or nutmeg. These spices complement the tropical flavors of pineapple beautifully and add a warm aroma that can make your cake pops feel even more nostalgic.

Another idea is to experiment with different fillings. You could mix in crushed pineapple or even coconut flakes right into the batter for a more tropical taste. If you prefer a chocolatey flavor, consider adding cocoa powder to the batter for a rich chocolate cake pop that pairs well with the sweet pineapple topping.

Questions About Recipes

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works beautifully and adds even more flavor.

→ What if I don’t have lollipop sticks?

You can use small skewers or even forks as a substitute.

→ How do I store leftovers?

Store them in an airtight container in the fridge for up to five days.

→ Can I make the pops ahead of time?

Absolutely! You can make the cake and pops a day ahead and store them in the fridge.

Pineapple Upside Down Cake Pops

I absolutely adore making Pineapple Upside Down Cake Pops! They combine the flavors of my favorite classic dessert with a fun, bite-sized twist. Each pop packs a delightful burst of juicy pineapple and the rich taste of buttery cake, all coated in a sweet glaze. They’re perfect for parties or just as a sweet treat at home. In just a few simple steps, you can impress your family and friends with these delicious little delights that are sure to become a hit!

Prep Time20 minutes
Cooking Duration25 minutes
Overall Time45 minutes

Created by: Ella

Recipe Type: Cozy Dessert Classics

Skill Level: Intermediate

Final Quantity: 12 pops

What You'll Need

For the Cake Pops

  1. 1 cup all-purpose flour
  2. 1/2 cup granulated sugar
  3. 1/2 cup unsalted butter, softened
  4. 2 eggs
  5. 1/4 cup milk
  6. 1 teaspoon vanilla extract
  7. 1/2 teaspoon baking powder
  8. 1/4 teaspoon salt

For the Topping

  1. 1 cup pineapple, chopped
  2. 1/4 cup brown sugar
  3. 1 tablespoon butter

For the Glaze

  1. 1/2 cup powdered sugar
  2. 1 tablespoon orange juice
  3. 1/2 teaspoon vanilla extract

How-To Steps

Step 01

In a skillet over medium heat, melt the butter. Add the chopped pineapple and brown sugar, cooking until the pineapple is caramelized, about 5 minutes. Set aside to cool.

Step 02

In a mixing bowl, cream together the softened butter and sugar. Add the eggs one at a time, beating well after each addition. Mix in the milk and vanilla extract. Gradually add flour, baking powder, and salt, stirring until combined.

Step 03

Fold the caramelized pineapple into the cake batter. Pour the batter into a greased baking dish and bake at 350°F (175°C) for 25 minutes or until a toothpick inserted in the center comes out clean.

Step 04

Once cooled, crumble the cake into a large bowl. Roll the crumbled cake into balls and insert a lollipop stick into each. Freeze for at least 30 minutes.

Step 05

In a small bowl, whisk together powdered sugar, orange juice, and vanilla extract until smooth.

Step 06

Dip each cake pop into the glaze and allow excess to drip off. Place on a baking sheet lined with parchment paper and let set. Serve chilled.

Extra Tips

  1. For best results, ensure the cake pops are thoroughly chilled before dipping to avoid them falling apart in the glaze.

Nutritional Breakdown (Per Serving)

  • Calories: 185 kcal
  • Total Fat: 8g
  • Saturated Fat: 4g
  • Cholesterol: 45mg
  • Sodium: 105mg
  • Total Carbohydrates: 26g
  • Dietary Fiber: 1g
  • Sugars: 15g
  • Protein: 2g