Wednesday, February 10, 2010

Pineapple Upside Down Cupcakes

Pineapple Upsidedown cake is my brother's favorite cake and he always gets one for his birthday. This year, since he was turning 30 and having a party, I decided that I'd put a twist on this traditional classic. I decided to make individual cupcakes for each guest. This recipe is great because it's easy to double, is moist and delicious, and keeps people coming back for more!

For the cupcakes, adding the pineapple juice really makes a difference because it incorporates the flavors of the topping. As a side note, I played around with the pineapple I used. Originally, the recipe called for crushed pineapple. I found that this made the topping stick to the cupcake pans and didn't come out looking quite so clean and pretty. The tidbits are small enough to fit on the cupcake and really made a difference. That being said, if your topping happens to stick slightly to the cupcake pan - DON'T PANIC! You can just scrape it off with a spoon and carefully arrange it atop the cupcake. No one will ever know! :)
Also, adding the sour cream to the batter makes this cake ultra moist and creamy - the cupcakes can sit out at a party without you having to worry they are getting dry. Once you make these, you can set them out and kick back and enjoy the party!


1 stick butter, melted
3/4 C. brown sugar, packed
1 (20 oz.) can pineapple tidbits in pineapple juice- drained, juice reserved
12 maraschino cherries - drained and halved

1 box yellow cake mix
1 C. sour cream
1/2 C. pineapple juice (reserved from pineapple tidbits)
1/3 C. vegetable oil
4 eggs
1 tsp. vanilla extract
flour for dusting pans

Preheat oven to 350 degrees. Lightly mist 24 cupcake cups with cooking spray and dust with flour.

For the topping, measure 1 tsp. of melted butter into each cupcake cup. Sprinkle with 1 heaping teaspoon of brown sugar on the melted butter. Spread about 1 T of the pineapple tidbits on top of the brown sugar. Gently place a cherry half in the center and push it down so the cherry is at the bottom, touching the pan.

For the cupcakes, blend cake mix, sour cream, pineapple juice, oil, eggs, and vanilla in a large bowl on low speed for 30 seconds. Scrape the bowl. Blend on medium speed until the batter is smooth and light, about 2 minutes. Spoon about 1/3 C of batter into each cupcake cup.

Bake at 350 degrees until the cupcakes are golden and spring back when lightly pressed with your finger - about 20 - 22 minutes. Immediately run a knife around the edges of the cupcakes to loosen and invert onto a platter. Cool at least 15 minutes before serving.


  1. Lisa - these look delicious and so easy. What a great twist on a yummy classic. Can't wait try them.

  2. I made these for Thanksgiving dinner yesterday and they turned out GREAT.. a huge hit with my family and friends. I am GIVING THANKS to you for mentioning that they might stick to the pan- they did, but you were indeed right that they were easily rearranged and no one noticed.
    I did end up needing more like 1+1/2 cans of pineapple chunks and closer to a full cup of brown sugar for the topping. Also, next time (because I definitely will make them again) I plan to add about 1/2 cup chopped pecans to the topping mixture. I think it would be a nice touch.
    Thanks for the great recipe! I plan on browsing around your blog and finding something else to make soon!
    Kristen in Nashville, TN :)