Pineapple Upside Down Cupcakes

These Pineapple Upside down Cupcakes have a tender yellow cupcake that is baked with a pineapple ring and an easy caramel sauce. The cupcake is turned upside down to serve, making the perfect single sized cake.

Love a good dessert with pineapple? Also check out this Dump Cake Recipe or Pineapple Dole Whip.

I don’t know if these Pineapple Upside Down Cupcakes would be considered vintage, but I do know they’ve been around for a long time because they are so delicious!

Based off of the bigger cake version, these cupcakes are more like mini, single serve cakes. Made in a jumbo muffin tin, these little cakes are the perfect dessert.

A moist yellow cupcake is baked with a simple caramel and pineapple slice on the bottom. Once baked, you turn the whole thing over, and serve each cupcake upside down so that the pineapple is now on the top.

If you are a fan of pineapple upside down cake, you definitely need to try this cupcake version!

Ingredients

Make sure you check out the recipe card below for full ingredient amounts and instructions.

• Flour: I use all-purpose flour.
• Baking Powder and Baking Soda: These are both used to give the cupcakes their lift.
• Salt: The salt balances out the flavors.
• Eggs: You will need both full eggs and egg yolks for this recipe.
• Sugar: For the cupcakes, you use regular granulated sugar.
• Oil: You need a neutral flavored oil – I like to use vegetable oil, but you can use what you like.
• Vanilla: A good dose of real vanilla extract gives these cupcakes a lot of flavor.
• Sour Cream: The sour cream keeps the cupcakes super moist and gives them a wonderful texture.
• Butter: The butter is used to make the caramel for the pineapple topping.
• Corn Syrup: The main purpose of the corn syrup is to keep the sugar from crystalizing. It also helps to sweeten the caramel.
• Brown Sugar: The brown sugar makes up the caramel around the pineapple.
• Pineapple: I think it is easiest to use canned pineapple. Since you need 12 rings, you’ll need one 20 oz can and a smaller 8 oz can.
• Cherries: The original recipe I had published here did not have the cherries, but they are a pretty iconic part of pineapple upside down cake!

How to Make Pineapple Upside Down Cupcakes

1: Whisk together the dry ingredients.

2: Mix together the eggs, egg yolks, and sugar. Beat this well – about 2 to 3 minutes, until it is lighter in color.

3: Add in the oil and the vanilla.

4: Mix in the sour cream just until you can’t see any white streaks.

5: Add the dry ingredients and mix just until combined. I like to do this by hand to make sure I don’t overmix.

6: Make the caramel by combining the butter, corn syrup, and brown sugar and cook it over medium heat until everything is smooth and the sugar is melted.

7: Divide the caramel between the 12 muffin cups.

8: Top each cup with a pineapple ring.

9: Place a cherry in the center of each pineapple ring.

10: Divide the batter evenly between all 12 cups. They should be almost all of the way full. Bake the cupcakes.

11: Remove from the oven and let them cool for about 5 minutes. Place a serving tray over the tin, then turn it all over.

12: Remove the tin and any parchment circles. Serve as is, or with a bit of whipped cream.

Tips and Tricks

You don’t want to wait more than 10 minutes before flipping your pineapple upside down cupcakes over. If you wait too long, the caramel mixture will stick and you’ll have a hard time getting the cupcakes out. I think 5 minutes is the perfect amount of waiting time.

If you are using fresh pineapple, you’ll want to make sure that you drain it and dry it as well as possible, as it will be juicier than canned pineapple.

Lining the cupcake tins helps them to release a little easier. If you choose not to line them, make sure you grease the pans very well.

If you don’t have 12 jumbo muffin tins, (mine only have 6 cavities each so I have to have 2 pans), you can bake them one at a time. But it is easiest if you have 2 pans. A lot of times, they will come in a 2 -pack.

My favorite way to eat these is when they are warm with some fresh whipped cream. They can be served room temperature or cold, though.

Make Ahead and Storage Instructions

You can make these cupcakes in advance, if needed. I wouldn’t make them more than 24 hour hours before serving. They will still be good up to 4 days after you make them, but they are best when they are fresher.

If making ahead of time, heat them slightly in the microwave or oven before serving.

Store the cupcakes in a covered container in the refrigerator.

More Fun Cupcake Recipes

Key Lime Cupcakes
Cookies and Cream Cupcakes
Circus Animal Cookie Cupcakes
Coconut Cherry Cupcakes
Banana Split Cupcakes

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Pineapple Upside Down Cupcakes

5 from 2 votes

Author: Deborah Harroun

Prep Time: 15 minutes minutes

Cook Time: 25 minutes minutes

Total Time: 40 minutes minutes

Servings: 12 servings

Course: Dessert

Cuisine: American

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These Pineapple Upside down Cupcakes have a tender yellow cupcake that is baked with a pineapple ring and an easy caramel sauce. The cupcake is turned upside down to serve, making the perfect single sized cake.

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Ingredients

• ▢ 2 1/2 cup all-purpose flour
• ▢ 1 teaspoon baking powder
• ▢ 1/2 teaspoon baking soda
• ▢ 1/2 teaspoon salt
• ▢ 2 large eggs
• ▢ 2 large egg yolks
• ▢ 2 cups sugar
• ▢ 1 cup neutral flavored oil such as vegetable or canola
• ▢ 2 teaspoons vanilla extract
• ▢ 1 cup sour cream
• ▢ 6 tablespoons unsalted butter
• ▢ 2 tablespoons light corn syrup
• ▢ 1 cup packed light brown sugar
• ▢ 12 pineapple slices*
• ▢ 12 maraschino cherries stems removed
• ▢ Fresh whipped cream for serving, optional

Instructions

• Preheat the oven to 350ºF. Line the bottom of 12 jumbo muffin tins** with parchment paper or wax paper. Spray the tins with nonstick cooking spray.
• In a bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.
• In the bowl of a stand mixer, or in another large bowl, beat the eggs, egg yolks, and the sugar together until light and fluffy, 2-3 minutes. Scrape down the sides of the bowl, then add in the  oil and the vanilla and continue to beat until combined. Add the sour cream and and mix until no streaks of white remain. Add the flour mixture and mix just until combined.
• In a saucepan, melt the butter with the corn syrup and the brown sugar. Cook over medium heat, stirring often, until the mixture is smooth and the sugar is dissolved. Remove from the heat.
• Carefully divide the caramel mixture between the 12 cups. Be careful not to touch it, as it is very hot. Each cup will need a heaping tablespoon of the caramel. (I used a small spring loaded cookie scoop.) Place a pineapple ring on top of the caramel in each cup, then place a cherry in the center of each pineapple.
• Divide the cupcake batter evenly between the 12 cups. The batter should nearly reach the top of the cup.
• Bake in the preheated oven until a toothpick inserted in the middle of the cupcake comes out clean or with just a few moist crumbs. When testing, make sure you don’t push the toothpick all the way down to the pineapple.
• When done, remove from the oven and let the cupcakes sit for 5 minutes. Carefully run a knife around the edges of the cupcakes, then carefully flip the pan over onto a serving platter to remove the cupcakes.
• Serve with freshly whipped cream, if desired.

Recipe Notes:

slightly adapted from cupcakes!

*If using canned pineapple, you will need 1 20-oz can and 1 8-oz can of pineapple in its own juice. You can also use fresh pineapple. If using fresh pineapple, try to dry it off before using as it usually has more moisture.

**Most jumbo muffin tins only have 6 cups. If you only have one pan, you’ll have to bake the cupcakes in 2 batches. This will work best if baked all at the same time, though.

Nutrition information provided as an estimate only. Various brands and products can change the counts. Any nutritional information should be used as a general guide. Nutritional information does not include whipped cream.

Nutrition Information

Serving: 1cupcake, Calories: 610kcal (31%), Carbohydrates: 83g (28%), Protein: 5g (10%), Fat: 29g (45%), Saturated Fat: 9g (56%), Polyunsaturated Fat: 16g, Cholesterol: 93mg (31%), Sodium: 252mg (11%), Fiber: 1g (4%), Sugar: 45g (50%)

Keywords: cupcake recipe, pineapple upside down cupcakes