If you’re looking for a delightful twist on a classic dessert, look no further than Pineapple Upside Down Cupcakes! These charming treats combine the nostalgic flavors of the traditional pineapple upside-down cake with the convenience and individual servings of cupcakes. Imagine biting into a moist cupcake topped with luscious caramelized pineapple and a sweet maraschino cherry. Not only are they visually appealing, but they also make for a fantastic dessert that can brighten up any occasion. Whether you’re hosting a gathering or simply satisfying your sweet tooth, Pineapple Upside Down Cupcakes are sure to impress your family and friends!

Ingredients List
- 1 cup all-purpose flour
- 1/2 cup sugar
- 1/2 cup unsalted butter, softened
- 2 large eggs
- 1/2 cup milk
- 1 tsp baking powder
- 1/4 tsp salt
- 1 cup crushed pineapple, drained
- 1/4 cup brown sugar
- 10 maraschino cherries
How to Prepare Pineapple Upside Down Cupcakes
Prepping the Oven and Ingredients
To begin your delicious journey with Pineapple Upside Down Cupcakes, start by preheating your oven to 350°F (175°C). This step is crucial as it ensures that your cupcakes bake evenly and rise perfectly. While the oven is warming up, gather all your ingredients and tools. You’ll need a mixing bowl, a muffin tin, a whisk, and a spatula. Make sure your unsalted butter is softened to room temperature for easier mixing. This will help create a light and fluffy batter.
Mixing the Batter
In a mixing bowl, cream together the softened butter and sugar using an electric mixer or a whisk. Beat the mixture until it becomes light and fluffy, which should take about 2-3 minutes. Next, add the two large eggs, one at a time, mixing well after each addition to ensure they are fully incorporated. Once the eggs are blended in, pour in the 1/2 cup of milk and mix until combined. In a separate bowl, whisk together the 1 cup of all-purpose flour, 1 tsp of baking powder, and 1/4 tsp of salt. Gradually add the dry ingredients to the wet mixture, stirring gently until just combined. Be careful not to overmix, as this can lead to dense cupcakes.

Preparing the Muffin Tin
Now it’s time to prepare your muffin tin! Start by adding 1/4 cup of brown sugar to the bottom of each muffin cup. This will create a lovely caramel base for your cupcakes. Next, evenly distribute the 1 cup of drained crushed pineapple over the brown sugar in each cup, followed by placing a maraschino cherry on top of the pineapple. This will not only add sweetness but also a pop of color to your Pineapple Upside Down Cupcakes.
Baking and Cooling
Carefully spoon the cupcake batter over the pineapple and cherry mixture in each muffin cup, filling them about two-thirds full. Place the muffin tin in the preheated oven and bake for 20-25 minutes, or until the cupcakes are golden brown and a toothpick inserted in the center comes out clean. Once baked, remove the cupcakes from the oven and let them cool in the tin for about 5 minutes. After that, invert the muffin tin onto a serving plate to reveal the delightful pineapple and cherry topping. Allow them to cool completely before serving, as this will help the flavors meld together beautifully.
Why You’ll Love This Recipe
- Quick Preparation: With a total time of just 40 minutes, you can whip up these delightful Pineapple Upside Down Cupcakes in no time, making them perfect for unexpected guests or last-minute celebrations.
- Delicious Flavors: The combination of moist vanilla cupcakes with sweet caramelized pineapple and cherries creates a mouthwatering flavor profile that will leave your taste buds wanting more.
- Fun Presentation: Each cupcake features a beautiful topping of pineapple and cherries, making them not only delicious but also visually appealing for any occasion.
- Individual Servings: Unlike traditional pineapple upside-down cake, these cupcakes offer a convenient and portion-controlled dessert, ideal for parties or dessert tables.
- Versatile Delight: Whether enjoyed at a birthday party, potluck, or just as a sweet treat at home, Pineapple Upside Down Cupcakes are a crowd-pleaser that everyone will love!
Tips for Success
To ensure your Pineapple Upside Down Cupcakes turn out perfectly every time, consider these pro tips:
- Use Quality Ingredients: The flavor of your cupcakes greatly depends on the quality of the ingredients. Use fresh eggs, high-quality butter, and ripe crushed pineapple for the best results. If possible, opt for fresh pineapple instead of canned for a more vibrant taste.
- Measure Accurately: Baking is a science, so be sure to measure all your ingredients precisely. Use a kitchen scale for the flour and sugar to ensure accuracy, which can lead to a better texture in your cupcakes.
- Don’t Overmix: When combining the wet and dry ingredients, mix until just combined. Overmixing can lead to dense cupcakes, so be gentle and stop as soon as you don’t see dry flour.
- Watch the Baking Time: Every oven is different, so keep an eye on your cupcakes as they bake. Start checking for doneness a few minutes before the suggested baking time, and use the toothpick test to ensure they’re cooked through.
- Store Properly: After your cupcakes have cooled completely, store them in an airtight container at room temperature for up to 3 days. If you want to keep them longer, consider freezing them. Wrap each cupcake individually in plastic wrap, then place them in a freezer-safe bag for up to 3 months. When ready to enjoy, simply thaw at room temperature.
Nutritional Information Disclaimer
Please note that the nutritional information provided for Pineapple Upside Down Cupcakes is an estimate and can vary based on the specific ingredients and brands used. Factors such as the type of butter, sugar, and any substitutions made can significantly alter the nutritional values. For the most accurate information, it is recommended to calculate the nutrition based on the exact ingredients you choose to use. Always consult a registered dietitian or nutritionist for tailored dietary advice.
FAQ Section
What If My Pineapple Upside Down Cupcakes Doesn’t Turn Out Right?
If your Pineapple Upside Down Cupcakes don’t turn out as expected, don’t worry! Common issues include cupcakes sticking to the muffin tin or being too dry. To avoid sticking, ensure you grease your muffin tin well before adding the brown sugar and pineapple mixture. If they are dry, it may be due to overbaking or incorrect measurements. Always check for doneness a few minutes before the suggested time.
Can I Prepare This in Advance?
Absolutely! Pineapple Upside Down Cupcakes can be made ahead of time. Bake them and let them cool completely before storing them in an airtight container. They can be kept at room temperature for up to three days or in the refrigerator for up to a week. If you prefer, you can also freeze them for longer storage. Just remember to thaw them before serving!
What Ingredients Can I Swap?
There are several ingredient swaps you can make for Pineapple Upside Down Cupcakes. If you need a dairy-free version, you can substitute the butter with a plant-based alternative and the milk with almond milk or coconut milk. For a gluten-free option, replace all-purpose flour with a gluten-free flour blend. You can also experiment with different toppings like mango or peaches for a fruity twist!
Storage & Reheating Instructions
To keep your Pineapple Upside Down Cupcakes fresh, store any leftovers in an airtight container at room temperature for up to 3 days. If you want to extend their shelf life, you can refrigerate them for up to a week. For longer storage, consider freezing the cupcakes. Wrap each cupcake individually in plastic wrap and place them in a freezer-safe bag. They can be frozen for up to 3 months. When you’re ready to enjoy them, simply thaw the cupcakes at room temperature for about 1-2 hours. If you prefer them warm, you can reheat them in the microwave for about 15-20 seconds, ensuring they’re not heated too long to avoid drying out.
Serving Suggestions
To elevate your Pineapple Upside Down Cupcakes and create a delightful dessert experience, consider pairing them with a scoop of vanilla ice cream or whipped cream. The creaminess complements the sweet and tangy flavors of the cupcakes beautifully. For an extra touch, drizzle some caramel sauce over the top or sprinkle toasted coconut flakes for added texture and flavor.
These cupcakes also make a wonderful addition to a tropical-themed dessert table, where they can be served alongside fresh fruit skewers or a refreshing fruit salad. If you want to impress your guests further, consider garnishing each cupcake with a sprig of mint for a pop of color and freshness. Enjoying these cupcakes with a cup of coffee or tea can also enhance their delicious flavors, making for a perfect afternoon treat!


Pineapple Upside Down Cupcakes
Ingredients
- 1 cup all-purpose flour
- 1/2 cup sugar
- 1/2 cup unsalted butter, softened
- 2 large eggs
- 1/2 cup milk
- 1 tsp baking powder
- 1/4 tsp salt
- 1 cup crushed pineapple, drained
- 1/4 cup brown sugar
- 10 maraschino cherries
Instructions
- Preheat your oven to 350°F (175°C).
- In a mixing bowl, cream together the butter and sugar.
- Add the eggs one at a time, mixing well after each addition.
- Mix in the milk and combine.
- In another bowl, whisk together the flour, baking powder, and salt.
- Gradually add the dry ingredients to the wet mixture until just combined.
- In a muffin tin, add brown sugar to the bottom of each cup.
- Place crushed pineapple and a cherry on top of the brown sugar in each cup.
- Spoon the batter over the pineapple and cherry.
- Bake for 20-25 minutes until golden brown.
- Let them cool for a few minutes before inverting onto a plate.
Notes
- Ensure the pineapple is well-drained to avoid excess moisture.
- You can use fresh pineapple for better flavor.
- Store leftovers in an airtight container.