These are, hands down, the BEST Homemade Pineapple Upside Down Cupcakes! Made entirely from scratch, they are still super quick and easy to whip up.
The secret spice ingredient makes them super scrumptious, nobody is ever going to guess WHAT you added!
This recipe is a wonderful twist on an old fashioned dessert favorite – everyone is going to love it! Bake them for a special occasion, a party or just because – your family will thank you for it.
So. Pineapple Upside Down Cupcakes.
They’re cute, right?
I love this mini twist on an old retro favorite. I remember my mom having a recipe book with retro recipes, and Pineapple Upside Down Cake was one of them.
It always intrigued me as a kid, because it’s just such an exciting moment when you invert the pan and finally get to see the glossy pineapple surface!
I know a lot of Pineapple Upside Down Cakes are made with boxed cake mix. And there’s nothing wrong with that!
Hey, I use it from time to time when I need to make a last minute Lemon Blueberry Sour Cream Coffee Cake!
But baking has always been a way for me to relax and blow off some steam, and since my husband and I have both been super busy lately I wanted to make a special treat for my girls.
This is the point where I’m telling you my baby isn’t allowed cake yet. She just grabs it any second I’m not 100% alert and shoves fistfuls into her mouth.
But if you crawl and stand up and go up the stairs at 7 months old, apparently you’re allowed to get yourself a slice of cake.
This Pineapple Upside Down Cupcakes recipe has a few twists that make it both easy and super delicious:
In all traditional recipes that I found, the butter and brown sugar for the topping got melted together.
But really, the sticky mess just annoyed me so much, ha!
So I tried to only melt the butter and just sprinkle the dry sugar into the muffin pan – and it works like a charm!
The secret spice…
Ever see recipes that claim to be SO easy, but then there’s ten spices to be measured out?
Yeah, I don’t do that anymore with two active kids around.
But I REALLY wanted a little more depth in these cupcakes, so I tried…
No kidding. There’s pumpkin spice in these cupcakes and it’s like a magic sprinkle of fairy dust.
Try it, even if it sounds strange to bust out the pumpkin spice in the middle of spring, it’s worth it.
More quick tips for the perfect Pineapple Upside Down Cupcakes:
Scoop the batter with a cookie or ice cream scoop, it’s mess-free, fast and easy!
After baking, cool the cakes in the pan for 4-5 minutes, but NOT for any longer, or else the sugary topping will start sticking to the muffin cups.
But do not under any circumstances try to invert them right out of the oven, because they do need a little time to set. Otherwise the hot butter/sugar syrup will run all over your hands, and it’s painful, and I know from experience.
Watch the Homemade Pineapple Upside Down Cupcakes recipe video here:
Here is the printable recipe for these scrumptious Homemade Pineapple Upside Down Cupcakes:
The Best Homemade Pineapple Upside Down Cupcakes (From Scratch!)
Made entirely from scratch, they are still super quick and easy to whip up. The secret spice ingredient makes them super scrumptious, nobody is ever going to guess WHAT you added!
For the Topping:
- 1/4 cup melted butter
- 1/4 cup brown sugar
- 20oz can pineapple tidbits in juice, drained and 1/2 cup juice reserved
For the Cake
- 1/4 cup butter
- 2/3 cup sugar
- 1 large egg
- 1 cup all-purpose flour
- 1.5 teaspoons pumpkin spice
- 1/2 teaspoon baking powder
- 1 tablespoon vanilla
Maraschino cherries, to garnish
Heat the oven to 360°F. Divide the melted butter between 12 muffin cups. Sprinkle about 1 teaspoon brown sugar in each cup and then divide the drained pineapple tidbits on top.
Blend the butter and sugar in a medium bowl with a hand mixer until soft. Add the egg and blend until light and fluffy. Add the remaining cake ingredients and reserved pineapple juice, mix until well combined.
Divide the batter between the prepared muffin cups and bake for 25-30 minutes, or until a toothpick inserted comes out clean.
Cool in the pan for 5 minutes, then invert on a rack and cool completely. Garnish with maraschino cherries.