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