by Amy Brinkley Published: Mar 17, 2014 Updated: May 14, 2020
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These little Pineapple Upside-Down Cupcakes are just as cute as they are delicious!
With the Easter holiday approaching, I thought back on what we used to eat at my grandma’s house for Easter dinner after church.
Somehow Grandma would always manage to throw together the BEST pineapple cake at the last minute. It was like she didn’t even have to think about what she was doing. It was from a box and she never read the directions or measured out any of the ingredients… but it always turned out phenomenal. I think Grandma always timed it at the very last minute so it would be piping hot from the oven when it was time for dessert.
I think if Grandma were here today, she’d sure enjoy these little Pineapple Upside-Down Cupcakes. I’ve seen them around online and have always thought they were so dainty… not to mention that everyone isn’t scrambling to get a slice of cake at the same time (like it used to be at Grandma’s).
It all starts with putting a spoonful of a brown sugar, butter and rum mixture in the bottom of a muffin tin that has been greased or sprayed with cooking spray.
Then place half of a maraschino cherry in the center and surround it with pineapple tidbits. Pour the batter over the top and bake… it’s as simple as that!
Pineapple Upside-Down Cupcakes
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5 from 1 review
- Total Time: 37 mins
- Yield: 24 cupcakes
Description
These easy and delicious cupcakes are always a welcomed dessert!
Ingredients
For the topping:
- ½ cup (1 stick) butter
- 1 cup dark brown sugar
- 2 teaspoons dark rum
- 12 maraschino cherries, sliced in half
- 1 (20 ounce) can pineapple tidbits, reserve juice for cake mix
For the cupcake batter:
- 1 package yellow cake mix (I used Duncan Heinz Classic Yellow, 16.5 ounce mix)
- Reserved pineapple juice (should yield 1 cup of juice)
- 3 large eggs
- ⅓ cup vegetable oil
Instructions
- Preheat your oven to 350 degrees F.
- Grease 2 (12 cup) muffin pans.
- In a small saucepan over medium heat, melt butter. Add brown sugar and rum. Bring to a gentle boil and cook for approximately 2 minutes (stirring often), or until thickened. Remove from heat.
- Spoon brown sugar mixture evenly into cupcake tins. Place half of a maraschino cherry in the center of each muffin section. Surround with pineapple tidbits.
- In a large bowl, beat cake mix, pineapple juice, eggs and oil on low speed for until moistened, about 30 seconds. Beat on medium speed for 2 minutes.
- Spoon cake batter over pineapple, filling almost to the top of each tin (mine were about ⅞ full).
- Bake 18 to 22 minutes, or until toothpick inserted in the center is removed clean.
- Immediately invert onto wire racks and allow to cool.
Notes
Adapted from Taste of Home and A Beautiful Mess
- Prep Time: 15 mins
- Cook Time: 22 mins
- Category: Dessert
- Method: Bake
- Cuisine: American
Reader Interactions
Comments
JenWhat dark rum do you use? Have you ever tried this with a spiced rum?
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- Amy @ The Blond Cook
Hi Jen, whatever your favorite brand of dark rum is will do… spiced rum will work as well and sounds delicious! Hope you enjoy them! 🙂
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- Stephanie
Hi can you use light brown sugar instead of dark with this recipe?
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- Amy @ The Blond Cook
Hi Stephanie, I’ve always used dark brown sugar in this recipe but I think it would probably be fine with light brown sugar. Let me know how it turns out and hope you enjoy them! 🙂
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- Farah Horigan
Hi! I just wanted to tell you. I made these substituting pineapple juice for the rum, for my girls daddy daughter dance last night. Since then I have had 3 mom’s call and text me asking for the recipe and 1 marriage proposal, which I turned down because I have a husband and 1 is enough. My husband also said that he witnessed many of the dad’s going back for seconds and 3rds! Thanks for the awesome recipe!
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- Amy @ The Blond Cook
Hi Farah, I laughed out loud at the marriage proposal! 🙂 So glad everyone enjoyed them and thank you so much!!!
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- sarah
Great Recipe ,i would love to make them on weekend looks juicy,Thanks for sharing
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- Amy @ The Blond CookSee AlsoEasy Gluten-Free Soft Pretzels
Thanks, Sarah!
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- Debbie
I bake a lot for Christmas, then package up and give away. Can these be frozen until I’ve finished all my baking?
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- Amy @ The Blond Cook
Hi Debbie, I’ve never frozen these so I can’t say. I wouldn’t think so because I think the cooked pineapple would probably we watery when thawed… but then again I’ve never frozen them so I can’t say for sure. Hope you enjoy these if you make them!
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- Lisa T
Can you bake then refrigerate a day before serving?
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- cheri williams
love pineapple upset down cake or cupcakes. my husbands grandma had a secret that absolutely is essential to the perfect dessert. lay out paper towels in 2 or 3 layers then lay out the pineapple and cherries allowing the fruit to dry some. this way your cake is not soggy in the center!
ooohh, the rum is a delicious add! thanks for the tip!!
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- Linzi Meyer
In stead of using the rum as a personal preference, could you use almond extract and how much?
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- Amy @ The Blond Cook
Hi Linzi, someone else asked the same question in the comments and I don’t know if they tried it or not. I’ve never tried it without rum so I can’t say from personal experience. However, it is such a small amount I would try using the extract (same amount). Please let me know how it turns out! 🙂
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- Judy Green
Vanilla works great in this recipe. However, I did cut the amount down somewhat as too much Vanilla tends to put an artificial flavor in this great recipe!
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- Amy @ The Blond Cook
Thanks Judy, glad you enjoyed it!
- Jennifer
Great recipe. Amounts were exactly as you posted. I might reduce butter next time. Thanks for sharing.
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- Amy @ The Blond Cook
Thanks Jennifer! 🙂
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- helen
Can i put the mixture into paper muffin cases instead of straight into the tin
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- Amy @ The Blond Cook
Hi Helen, yes you can!
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Is there an alternative to rum for the brown sugar mixture base?
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- Amy @ The Blond Cook
Hi Helen! I’ve never tried it without using rum, but I’m thinking that since it’s such a small amount, it might not hurt to omit it. Vanilla extract might be a good alternative also. Please let me know how it turns out if you try it!
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- Farah Horigan
I used pineapple juice instead of rum. I made mine for a daddy daughter dance at my kids school. So the rum wasn’t an appropriate additive.
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- Tara
Are you using standard size muffins tins or
mini muffin tins for this recipe?Reply
- Amy @ The Blond Cook
Hi Tara, I used standard size muffin tins… hope you enjoy them if you make them! 🙂
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- Tara
Perfect , thank you! Planning to make them for my grandmother’s 90th birthday luau!
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