Pineapple Upside-Down Cupcakes

These fun and personal-sized pineapple upside-down cupcakes feature a fluffy vanilla cupcake base topped with caramelized pineapple and cherries. They taste just like the classic cake, but are faster and more portable! Recipe includes a how-to video tutorial!

Mini Pineapple Upside-Down Cakes

While my classic pineapple upside-down cake has been around for a while, I’ve received enough requests on how to turn it into pineapple upside-down cupcakes that I felt a stand-alone post was in order. Truthfully, the actual recipe varies only slightly from the original, but the technique is different enough that I think this post (and video!) is worth sharing independently rather than trying to cram it into a note at the bottom of the original.

These cupcakes have a soft, moist, and tender vanilla cupcake base borrowed from my vanilla cake recipe. They’re topped off (technically the bottom, until you flip them over) with a brown sugar caramelized fruit topping that is uniquely trademarked to this cake and so flavorful. There’s a reason this cake is a classic–it’s just so good!

Why You’ll Love This Recipe

• You get the ultimate pineapple-to cake ratio in each bite! As a pineapple lover, I am a big fan of the cupcake version for this reason.
• Faster than making a whole cake, and there’s no slicing or decorating needed!
• Flips out of the pan beautifully! Just make sure to grease your pan really well and remove the cupcakes within a few minutes, and you should be just fine. I describe how to do this in more detail below.
• Perfectly miniature! Just like my mini cheesecakes or pavlova, these tiny cakes would be so cute as a baby shower dessert or tea party treat.

Ingredients

All of the ingredients used here are the same ones you’ll find in the larger cake-version of today’s recipe. I wanted to keep things the same so you had truly classic results.

• Pineapple. Fresh or canned pineapple will work fine here. I like canned pineapple chunks and they are the proper thickness for cooking the cupcakes according to the recipe, but in a pinch you could use the rings. If you do, you’ll still need to cut them into pieces to fit and, since they are typically thinner than the chunks, the cupcakes will likely bake faster. Make sure to drain your pineapple well; too much juice can cause the cupcake pan to overflow.
• Sugar. Light brown sugar works best for the caramelized fruit topping and granulated sugar is ideal for the cupcakes themselves.
• Cherries. Use pitted, stemless maraschino cherries for classic flavor.
• Buttermilk. Buttermilk keeps our pineapple upside-down cupcakes moist. This is important, since you will have to store these cupcakes in the fridge (and the fridge tends to dry out cakes). Real buttermilk is always my preference, but my easy buttermilk substitute will work in a pinch (and you can substitute pineapple juice for the lemon or vinegar I typically use). While I’ve had a few readers use pineapple juice in place of the buttermilk completely, I personally prefer to use buttermilk here and think it gives the most authentic results with the fluffiest crumb.
• Vanilla. Sometimes vanilla and fresh fruit don’t play nicely together (one of the reason I omit this ingredient in my lemon cheesecake), but in this instance the cake base should have a classic vanilla flavor. It works well here, especially against the rich caramelized flavor of the toppings.

SAM’S TIP: If you use canned pineapple, one 20 oz can will not be enough. Typically you’ll need one additional small can for the last cupcake or so.

Remember, this is just an overview of the ingredients I used and why. For the full recipe please scroll down to the bottom of the post!

How to Make Pineapple Upside-Down Cupcakes

1. Prepare your pan – thoroughly butter your cupcake pan, then add a tablespoon of brown sugar to the bottom of each well. Top with pineapple and a maraschino cherry, then set this aside.
2. Cream the butter and sugar with an electric mixer until light and fluffy.
3. Stir in the eggs and vanilla, then set this aside. Whisk together the dry ingredients in a separate bowl.
4. Add ¼ of the dry ingredients and stir with a spatula until just combined.

5. Add ⅓ of the buttermilk, then stir again with a spatula to combine. Continue alternating between flour and buttermilk until you have added everything. Do not use a mixer at this point and do not over-mix (remember my tips from my post on tips to keep from ruining your homemade cakes!)!
6. Portion the batter into your cupcake pan and use a spoon to spread/smooth the tops. Be careful not to overfill. If you have extra batter, discard it.
7. Bake on a foil lined rimmed baking sheet until a toothpick comes out clean or with moist crumbs. Let the cupcakes cool for 5 minutes, then gently loosen them from the pan with a knife.
8. Invert the cupcakes onto a cooling rack and let cool slightly before serving.

SAM’S TIP: Some people have reported that the caramelized topping overflows from the cupcake tin while baking. This is likely related to the juiciness of the pineapples or overfilling the cupcake liners. To combat this, simply place your cupcake tray on a rimmed foil lined baking sheet. This way, if any spilling occurs, this will be much easier to clean up than trying to clean your oven!

Frequently Asked Questions

If you’ve tried my original cake version, I’d love to hear what you think of this mini one 😊

Enjoy!

Let’s bake together! Subscribe to my newsletter to be notified of all the newest recipes, and find my free recipe tutorials on YouTube 💜

Pineapple Upside-Down Cupcakes

Pineapple upside-down cupcakes feature a fluffy vanilla cupcake base topped with caramelized pineapple and cherries. They taste just like the cake, but are faster and more portable!

Recipe includes a how-to video!

5 from 3 votes

Print Pin Rate

Cook ModePrevent your screen from going dark

Course: cupcakes, Dessert

Cuisine: American

Prep Time: 25 minutes minutes

Cook Time: 25 minutes minutes

Total Time: 50 minutes minutes

Servings: 12 cupcakes

Calories: 322kcal

Author: Sam Merritt

Ingredients

For the topping

• ▢ 6 Tablespoons (85 g) salted butter melted
• ▢ 12 Tablespoons (150 g) light brown sugar (¾ cup) firmly packed
• ▢ 2 ⅓ cups (438 g) pineapple chunks drained/patted dry (see note)
• ▢ 12 Maraschino cherries drained

For the cupcakes

• ▢ ½ cup (113 g) unsalted butter softened to room temperature
• ▢ ¾ cup (150 g) granulated sugar
• ▢ 2 large eggs room temperature preferred
• ▢ 1 teaspoon vanilla extract
• ▢ 1 ½ cups (187 g) all-purpose flour
• ▢ 1 ½ teaspoons baking powder.
• ▢ ¼ teaspoon table salt,
• ▢ ½ cup (118 ml) buttermilk

Recommended Equipment

• ▢
  Cupcake tin
• ▢
  Baking sheet
• ▢
  Mixing bowls

Instructions

• Preheat oven to 350F (175C). Evenly divide butter into the bottom of each cupcake well and use a pastry brush to lightly brush the sides with butter as well.
  6 Tablespoons (85 g) salted butter
• Sprinkle 1 Tablespoon (12 grams) of sugar evenly into the bottom of each cupcake well.
  12 Tablespoons (150 g) light brown sugar
• Arrange 4 pineapple chunks in a flower pattern over the butter and brown sugar and press a Maraschino cherry into the center of each “flower”. Set aside as you prepare your cupcake batter.
  2 ⅓ cups (438 g) pineapple chunks, 12 Maraschino cherries

For the cupcakes

• Combine butter and sugar in a medium-sized mixing bowl (or the bowl of a stand mixer fitted with the paddle attachment) and use an electric mixer to beat until light and fluffy.
  ½ cup (113 g) unsalted butter, ¾ cup (150 g) granulated sugar
• Add eggs and vanilla extract and beat well.
  2 large eggs, 1 teaspoon vanilla extract
• In a separate mixing bowl, whisk together flour, baking powder and salt.
  1 ½ cups (187 g) all-purpose flour, 1 ½ teaspoons baking powder., ¼ teaspoon table salt,
• Alternate adding the flour mixture and the buttermilk to the batter, starting and ending with the flour mixture and stirring until just combined after each addition (I add the flour mixture in 4 parts and the buttermilk in 3 parts and recommend doing this part gently by hand with a spatula to not over-mix).
  ½ cup (118 ml) buttermilk
• Evenly divide the cupcake batter into your prepared pan, filling each cupcake well to the rim (don’t overfill, if you have excess batter discard it). The batter will be thick, so use a spoon to gently spread it into each cupcake well.
• Place cupcake tin on a foil lined rimmed baking sheet (in case of spills) and transfer to center rack of 350F (175C) preheated oven and bake for 22-25 minutes and a toothpick inserted in the center comes out clean or with moist crumbs.
• Allow cupcakes to cool in pan for 5 minutes then use a knife to gently loosen the cupcake from the edges of the pan before inverting. Place a wire cooling rack over the cupcake tin and, carefully, using potholders (the tin will be very hot!) keep the cooling rack pressed securely against the tin and invert cupcakes onto cooling rack. Lift the tin, the cupcakes should release easily.
• Allow to cool a bit before serving. These are great served warm and we love them with vanilla ice cream, too!

Notes

Pineapple chunks

I use canned pineapple chunks in 100% pineapple juice. Drain the pineapple chunks and pat dry. I find a single can is usually not enough, you’ll need at least 21 oz of canned pineapple chunks.

Doubling

You can easily double this recipe for 24 cupcakes.

Storing

Store in an airtight container in the refrigerator and enjoy within 2-3 days.

Nutrition

Serving: 1cupcake | Calories: 322kcal | Carbohydrates: 46g | Protein: 3g | Fat: 15g | Saturated Fat: 9g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 4g | Trans Fat: 1g | Cholesterol: 64mg | Sodium: 159mg | Potassium: 119mg | Fiber: 1g | Sugar: 33g | Vitamin A: 493IU | Vitamin C: 4mg | Calcium: 79mg | Iron: 1mg

Nutritional information is based on third-party calculations and should be considered an estimate only. Actual nutritional content will vary based upon brands used, measuring methods, cooking method, portion sizes, and more.

Tried this recipe? Show me on Instagram!Mention @SugarSpun_Sam or tag #sugarspunrun!

I first shared this recipe in 2017 over on my friend The Recipe Critic’s website!

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