Mini Pineapple Upside-Down Cakes

Pineapple upside down cakes

Made in a jumbo muffin pan, these Mini Pineapple Upside-Down Cakes are just the right size for snacking! With a moist cake, brown sugar caramel, a caramelized pineapple ring, and that traditional maraschino cherry, you may find them difficult to share!

The best thing about a mini dessert is that it’s a self contained serving.  You might feel guilty about having a big slice of pie or cake; how big should you slice it, does the height or width matter, what about the number number of layers?  Do those need to be accounted for?  But a mini dessert is already divided into its perfect serving size!  No crazy decision making needed.

This recipe makes 12 mini pineapple upside-down cakes, enough to share with a lot of people and still keep a couple for yourself!  I use 2 jumbo muffin pans for the recipe, mostly because the pineapple rings fit perfectly in the bottom of each muffin cup.  See? Even the universe was telling me that these were the perfect “serving size.”


Mini Pineapple Upside-Down Cakes

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Topping (which, I know, starts on the bottom. But it ends up on the top, so: Topping)

  • 1/4 cup butter (half a stick) melted
  • 3/4 cup dark brown sugar (if you only have light brown sugar, that's fine. I just like the darker color and depth of flavor from dark.)
  • 12 maraschino cherries
  • 12 pineapple rings (you'll need 2 cans. Each can has 10 rings, so you'll have to eat the rest. Too bad. Save the juice. We'll use it in the cake batter!)

Cake Batter

  • 2 1/4 cup all-purpose flour
  • 1 1/2 cup white sugar
  • 1 1/2 tsp baking powder
  • 1/2 tsp salt
  • 2 eggs
  • 1/4 cup butter, or half a stick, melted
  • 1 tsp vanilla extract
  • 1/2 cup pineapple juice that you saved like I told you to, remember?
  • 1/4 cup sour cream


  • Preheat your oven to 350°. Spray the inside of 2 jumbo muffin pans with non-stick spray. Into each muffin cup, spoon 1 teaspoon of melted butter and sprinkle in 1 tablespoon of dark brown sugar. Lay a pineapple ring on top of that. It should fit perfectly. If it doesn't, just trim out a piece of each ring until it fits. You can eat that bit, that's fine. It's fruit. As you can see, I had to do exactly that in one of my pans. And yes, my pans are mismatched. I don't even remember buying these pans, so welcome to real life. We adjust. Place a maraschino cherry in the center of each ring. Isn't that pretty? Let's make some cake.
  • Whisk together the flour, salt, sugar, and baking powder in a large bowl. In a small bowl, whisk together your eggs, melted butter, vanilla, pineapple juice, and sour cream. Pour the wet ingredients into the dry ingredients and mix until fully combined. Fill each muffin cup 2/3 full. You should have just enough batter to fill each one. If you have a little batter left over, just distribute it evenly amongst all the muffin cups. Tap your pans lightly against the counter to remove any large air bubbles.
  • Bake at 350° for 20-25 minutes, or until a toothpick inserted in the center of a cake comes out clean. They will look delightfully fluffy and golden! See?!
  • Allow the cakes to cool for 5-10 minutes in the pan. Here's the cool part that will make you feel totally chef-y. Use a potholder to hold the bottom of the muffin pan (remember, it's still warm!), and then place a sheet pan over the top of the muffin pan. Grip securely with both hands, and flip it all over in one quick motion. Give it a little shake and all the cakes should come out easily. You'll be able to hear and feel when they've all dropped down onto the sheet pan. It's okay if one or two pineapples stay in the muffin pan. Just gently remove them and place them on their cakes. They'll taste just as delightful. If it still looks a little wonky and you're not-so-sure about it, just eat those first for quality control. Share the rest with friends and family. Or not. You did all the hard work. You get to decide who is cake worthy.

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