Pineapple Upside Down Cupcakes

If you love the old-fashioned classic, you must give these delicious Pineapple Upside Down Cupcakes a try! Easy and always a hit with great reviews.

Why You Will Love These Pineapple Upside Down Cupcakes

If you grew up loving pineapple upside-down cake, these little cupcakes will take you right back. Made with sweet pineapple, cherries, buttery brown sugar, and soft cake, they have that classic old-fashioned flavor everyone remembers. What is great is we used a cake mix in this recipe and no one will ever know! The flavor is wonderful and my family loves them. Great for family gatherings, church suppers, potlucks, and anytime you want a dessert that feels nostalgic and special without much fuss.

Why These Are Perfect For Any Gathering

These are so great since they are really like an individual serving! They’re beautiful on a dessert tray, easy to serve, and always one of the first things to disappear. If you love old-fashioned desserts that never go out of style, this recipe belongs in your collection. We make them with pinapple rings and with crushed pineapple and they look beautiful!

How Many Does It Make?

This recipe makes between 18 and 24 cupcakes, depending on how you do it. We use a large cup muffin tin (6 muffins) for the pineapple rings and a regular muffin tin for the crushed pineapple. So we get 18 cupcakes, but if you used just 2 regular muffin tins, you would get 24.

Tips and Storage

These can stay our for a day but after that we suggest putting them in the refrigerator. You can make these a day in advance and we think they are great the next day. We have not tried freezing them but they would probably freeze just fine.

Other Delicious Pineapple Recipes:

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Judy Yeager

These Pineapple Upside Down Cupcakes is a dessert favorite made with pineapple, cherries, brown sugar, and a moist cake baked right into individual servings. Perfect for potlucks, holidays, and family gatherings.

Prep Time 20 minutes

Cook Time 25 minutes

Total Time 45 minutes

Course Dessert

Cuisine American, southern

1 box Pillsbury Moist Supreme Classic Yellow Cake Mix
1 (3.4 ounce) Vanilla Instant Pudding
3 eggs
1/3 cup oil
2/3 cup pineapple juice
1/3 cup milk
1 15.25 ounce can pineapple slices, drained (save juice)
1 20 ounce can crushed pineapple, drained (save juice)

Topping

1 stick butter melted
1 cup brown sugar
maraschino cherries

Spray muffin tins well with cooking spray. Melt butter and sugar together on top of the stove. Add 1 tablespoon sugar mixture to each muffin cup. Next, put in 1 tablespoon crushed, drained pineapple or 1 pineapple slice in bottom of each cup. In a large bowl mix cake mix, pudding mix, eggs, oil, juice and milk with mixer.
Fill cups 1/2 to 3/4 full with cake mix. Bake in preheated 350 degree oven for 25 minutes. Remove and let cool at least 10 minutes. Run a knife around the edges to loosen muffins from cups before removing. Turn cupcakes upside down on a platter and add cherries.

I used one regular 12 cup muffin tin and one large 6 cup tin to make these. This way the recipe made 18 cupcakes.. If just using regular 12 cup tins, it should make about 24 cupcakes. You could use all crushed pineapple or all pineapple rings as well. I wanted to try them both ways to see how they turned out. I think the pineapple rings work better in the larger cup muffin tins.) These would be good topped with whipped cream and you could add nuts to the mix.

Keyword Pineapple Upside down cupcakes

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