If you love old-fashioned classics, you’ll want to try these delicious Pineapple Upside Down Cupcakes. It’s easy and always popular with great reviews.

Why you’ll love these Pineapple Upside Down Cupcakes
If you grew up loving pineapple upside-down cakes, you’ll be instantly drawn back to these little cupcakes. Made with sweet pineapple, cherries, buttery brown sugar, and soft cake, it’s the classic flavor everyone remembers. The great thing is that this recipe uses a cake mix and no one will notice. It tastes great and my family loves it too. Perfect for family gatherings, church dinners, potlucks, or any time you want a nostalgic and special dessert without the hassle.
Why it’s perfect for any gathering
It’s really amazing because it feels like a full-fledged meal! It looks beautiful on a dessert tray, is easy to serve, and is always one of the first things to disappear. If you like old-fashioned desserts that never go out of style, this recipe will become part of your collection. It’s made with pineapple rings and crushed pineapple, so it looks beautiful.
How many can you make?
This recipe makes 18-24 cupcakes, depending on how you do it. Use a large cup muffin tin (makes 6 muffins) for the pineapple rings, and a regular muffin tin for the crushed pineapple. So you’ll get 18 cupcakes, but if you used just two regular muffin tins you’d get 24.


Tips and storage
It’s fine for about a day, but after that we recommend storing it in the refrigerator. If you make it the day before, it will be delicious the next day. I haven’t tried freezing it, but it probably will work fine.
More delicious pineapple recipes:


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pineapple upside down cupcake
These Pineapple Upside Down Cupcakes are a popular dessert made with pineapple, cherries, brown sugar, and a moist cake baked directly into individual servings. Perfect for potlucks, holidays, and family gatherings.
topping
1 stick butter melted1 cup brown sugarmaraschino cherry
Spray muffin tins well with cooking spray. Melt the butter and sugar together on the stove. Add 1 tablespoon sugar mixture to each muffin cup. Then place 1 tablespoon of crushed, drained pineapple or 1 pineapple slice in the bottom of each cup. Combine cake mix, pudding mix, eggs, oil, juice, and milk in a large bowl with a mixer.
Fill cup 1/2 to 3/4 full with cake mix. Bake in a preheated 350 degree oven for 25 minutes. Remove and let cool for at least 10 minutes. Run a knife around the edge of the cup to loosen the muffin from the cup before removing. Flip the cupcakes onto a plate and add the cherries.
To make these, I used one regular 12-cup muffin pan and one large 6-cup muffin pan. This recipe made 18 cupcakes. If you only use a regular 12 cup tin, you should be able to make about 24 cupcakes. You can also use all the crushed pineapple or all the pineapple rings. I wanted to try both methods and see the results. I think the pineapple rings work better in a larger cup muffin tin. ) You can also top it with whipped cream or add some nuts to the mix.
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