Pineapple Upside Down Cake Pops

Highlighted under: Everyday Dessert Recipes

I love baking and experimenting with new desserts, and these Pineapple Upside Down Cake Pops have quickly become a favorite in my household. The moist, buttery cake combined with the sweet caramelized pineapple creates a delightful treat that's fun to eat. These pops not only look adorable but also capture the classic flavors of the traditional upside down cake in a single bite. Perfect for summer parties or just a sweet craving, they are sure to impress family and friends alike!

Emily

Created by

Emily

Last updated on 2026-02-04T17:45:27.491Z

When I first tried making cake pops, I was amazed at how versatile they could be. I decided to put a tropical twist on the classic treat by using pineapple and brown sugar, reminiscent of the upside down cake I loved growing up. The cake stays moist thanks to the pineapple, and the pops can be customized with colorful sprinkles to make them extra festive!

One tip I found really helpful is to let the cake cool completely before popping them on sticks. This helps them hold their shape better and prevents the chocolate coating from sliding off. I also love using lollipop sticks for a fun presentation and easier handling!

You'll Love These Cake Pops Because

  • The unique twist on a nostalgic dessert favorite
  • Sweet and tangy flavors delight your taste buds
  • Fun and portable treats for any occasion

Perfecting the Cake Batter

The key to a moist and flavorful Pineapple Upside Down Cake Pop lies in the cake batter. Creaming the softened butter with sugar until light and fluffy is essential; this step incorporates air into the mixture, leading to a lighter texture. When adding the crushed pineapple, ensure it is well-drained to avoid excess moisture, which can make the pops soggy. The combination of pineapple and butter creates a unique richness that complements the sweetness of the sugar perfectly.

Introduce the dry ingredients gradually to maintain a smooth batter. Mixing just until combined—avoiding over-mixing—is crucial to prevent the cake from becoming dense. If you notice the batter is too thick, you can add a teaspoon or two of milk to achieve the desired consistency. Keep an eye on it; the batter should be thick enough to hold its shape but smooth enough to fill the cake pop cavities easily.

Layering for Flavor

Layering the cake pops with brown sugar and diced pineapple is where the magic happens. The brown sugar provides a deep, caramel flavor that pairs beautifully with the tropical pineapple. By placing the pineapple mixture in the middle of the batter, you're ensuring that each pop contains pockets of concentrated sweetness, mimicking the classic upside-down cake experience. Make sure the pineapple is diced finely to distribute the flavor evenly throughout the pop.

When filling the cake pop cavities, be mindful not to overfill. A filling of about halfway with batter, followed by the brown sugar and pineapple layer, ensures that there’s enough room for the top layer of batter. This layering technique is essential not only for flavor but also for achieving that perfect dome shape on top once baked. If your pops look uneven, gently press them down with a spoon before baking to achieve a more uniform appearance.

Tips for Coating and Decorating

Coating the cake pops in chocolate or candy melts adds a delightful crunch and richness that beautifully contrasts the soft cake inside. To achieve a smooth coating, melt your chocolate or candy melts in short intervals in the microwave, stirring in between to avoid burning. The coating should be glossy and fluid—if it’s too thick, add a small amount of vegetable oil to thin it out. This ensures an even coverage and avoids clumpy spots on your pops.

After dipping the pops, allow the excess chocolate to drip off before setting them on a cooling rack. This helps prevent unsightly pooling at the base of the pops. If you're adding sprinkles, do so while the coating is still wet for better adherence. For extra flair, consider using colored candy melts to match the occasion or theme. These little touches can elevate your pops from simple treats to eye-catching desserts.

Ingredients

For the Cake Pops

  • 1 cup all-purpose flour
  • 3/4 cup sugar
  • 1/2 cup unsalted butter, softened
  • 2 large eggs
  • 1/4 cup crushed pineapple (drained)
  • 1 tsp baking powder
  • 1/2 tsp vanilla extract
  • 1/4 tsp salt

For the Topping

  • 1/2 cup brown sugar
  • 1 cup diced pineapple
  • 12 lollipop sticks
  • Chocolate coating or candy melts
  • Sprinkles (optional)

Make sure to prep all your ingredients ahead of time for a smooth baking experience!

Instructions

Prepare the Pan

Preheat your oven to 350°F (175°C) and grease a cake pop pan.

Mix the Batter

In a bowl, cream the softened butter and sugar together. Add in eggs one at a time, mixing well after each addition. Stir in crushed pineapple, vanilla extract, and mix until combined. In another bowl, whisk together flour, baking powder, and salt. Gradually add dry ingredients to wet ingredients, mixing until smooth.

Fill the Pan

Pour a small amount of the batter into each cake pop cavity, filling about halfway. Top with a layer of brown sugar and diced pineapple mixture, then cover with more batter until full.

Bake and Cool

Bake for about 30 minutes or until a toothpick inserted in the center comes out clean. Allow to cool completely.

Coat the Pops

Melt chocolate coating or candy melts according to package instructions. Dip the tip of each lollipop stick into the melted chocolate, then insert it into the center of the cake pops. Once set, dip the entire pop in the melted coating and allow to set on a cooling rack. Optionally, add sprinkles before they dry.

Allow the pops to cool completely in the fridge for the best flavor and texture!

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Pro Tips

  • Customize your cake pops by adding different flavors of cake or using white chocolate coating. These pops are best enjoyed within a few days of making them.

Storage and Make-Ahead Options

These Pineapple Upside Down Cake Pops can be made ahead of time, making them a great option for parties. Once fully coated and set, store them in an airtight container at room temperature for up to three days. For longer storage, place them in the refrigerator, where they can last up to a week. If you choose to freeze them, ensure they are well-wrapped in plastic wrap and placed in a freezer-safe container. They can be frozen for up to a month; just thaw them in the refrigerator before serving.

To maintain their texture and flavor, it's best to coat them just before serving if possible. Freezing can sometimes affect the chocolate coating’s sheen, so adding a fresh coat right before serving can coax back that glossy finish. If you're short on time, pre-bake the cake pops and freeze them before dipping, which allows you to whip them out and coat them quickly when needed.

Variations and Serving Suggestions

While the classic version is delightful, consider mixing up the flavors by incorporating coconut or even lime zest into the batter for a tropical twist. You could also add a splash of rum to the batter for a fun adult version. Alternatively, try dipping the pops in white chocolate and then rolling them in toasted coconut for an irresistible tropical treat that celebrates summer flavors.

For serving, these cake pops pair beautifully with a scoop of vanilla ice cream or a splash of whipped cream. A drizzle of caramel sauce can also enhance their presentation and taste. For a fun party idea, organize a cake pop decorating station where guests can add their own toppings—this interactive element adds joy to the experience and personalizes the treats.

Questions About Recipes

→ Can I make these cake pops ahead of time?

Yes, you can prepare the cake pops a day in advance and store them in the fridge until you're ready to serve.

→ What can I use instead of pineapple?

You can substitute with other fruits like peaches or cherries, just ensure they're well-drained.

→ Why is my chocolate coating not sticking?

Ensure that the cake pops are completely cooled and that you are dipping into the melted chocolate while it's still warm.

→ How can I make these pops more festive?

Use colorful candy melts and a variety of sprinkles to match the occasion or holiday!

Pineapple Upside Down Cake Pops

I love baking and experimenting with new desserts, and these Pineapple Upside Down Cake Pops have quickly become a favorite in my household. The moist, buttery cake combined with the sweet caramelized pineapple creates a delightful treat that's fun to eat. These pops not only look adorable but also capture the classic flavors of the traditional upside down cake in a single bite. Perfect for summer parties or just a sweet craving, they are sure to impress family and friends alike!

Prep Time20
Cooking Duration30
Overall Time50

Created by: Emily

Recipe Type: Everyday Dessert Recipes

Skill Level: Intermediate

Final Quantity: 12 pops

What You'll Need

For the Cake Pops

  1. 1 cup all-purpose flour
  2. 3/4 cup sugar
  3. 1/2 cup unsalted butter, softened
  4. 2 large eggs
  5. 1/4 cup crushed pineapple (drained)
  6. 1 tsp baking powder
  7. 1/2 tsp vanilla extract
  8. 1/4 tsp salt

For the Topping

  1. 1/2 cup brown sugar
  2. 1 cup diced pineapple
  3. 12 lollipop sticks
  4. Chocolate coating or candy melts
  5. Sprinkles (optional)

How-To Steps

Step 01

Preheat your oven to 350°F (175°C) and grease a cake pop pan.

Step 02

In a bowl, cream the softened butter and sugar together. Add in eggs one at a time, mixing well after each addition. Stir in crushed pineapple, vanilla extract, and mix until combined. In another bowl, whisk together flour, baking powder, and salt. Gradually add dry ingredients to wet ingredients, mixing until smooth.

Step 03

Pour a small amount of the batter into each cake pop cavity, filling about halfway. Top with a layer of brown sugar and diced pineapple mixture, then cover with more batter until full.

Step 04

Bake for about 30 minutes or until a toothpick inserted in the center comes out clean. Allow to cool completely.

Step 05

Melt chocolate coating or candy melts according to package instructions. Dip the tip of each lollipop stick into the melted chocolate, then insert it into the center of the cake pops. Once set, dip the entire pop in the melted coating and allow to set on a cooling rack. Optionally, add sprinkles before they dry.

Extra Tips

  1. Customize your cake pops by adding different flavors of cake or using white chocolate coating. These pops are best enjoyed within a few days of making them.

Nutritional Breakdown (Per Serving)

  • Calories: 220 kcal
  • Total Fat: 10g
  • Saturated Fat: 5g
  • Cholesterol: 40mg
  • Sodium: 100mg
  • Total Carbohydrates: 30g
  • Dietary Fiber: 1g
  • Sugars: 18g
  • Protein: 2g