Friday, July 24, 2009

Pineapple Upside-down Cupcakes

Wow! Cupcake Friday came around pretty quick this week…seeing as how I just posted the Buckeye Cupcakes on Tuesday. But Friday it is. And have I got a good one for you this week.

Among our talented members of Dishing-It-Up! is one of the editors of “Family Fun Magazine”, Ellen Harter Wall. Through Ellen’s generosity I get to enjoy this great magazine every month. So when I opened the August issue and saw Pineapple Upside-down Cupcakes I knew exactly what the next Friday’s cupcake was going to be. I love pineapple upside down anything!

Put that in a cupcake and I’m in heaven! I just love the crunchy, crusty, buttery, baked sugary deliciousness of the topping, with pieces of juicy pineapple and a maraschino cherry in the middle! Oh-my-gosh! (Excuse me while I wipe the drool from my keyboard.) Then once your taste buds pass the topping, they hit the moist & bouncy cake that supports the toppings. That is if we’re talking good pineapple upside-down cake.

So I had pretty high expectations when I started to bake these cupcakes. The recipe looked straightforward. And the results? Well…let me tell you these cupcakes are so incredibly delicious that I wanted to eat them in multiples. (And Bob was out of town so I could have done just that with a reasonable chance of getting away with it. However, he reads the recipes and knows how many there should be and he gets just the teensiest bit testy if he doesn’t get his share. I’m just sayin’.)

So I limited myself to one…until morning. And then I had another for breakfast. I knew I’d better start giving them away or I’d eat the entire batch! So saving back Bob’s rations, I “doled” (get it? “doled”) out cupcakes to some willing taste testers; “Hotmom” (aka: Brooke), and Clint & Virna. All three gave them a definite thumbs up!

Pineapple Upside-down CupcakesFrom the August 2009 “Family Fun Magazine”Nancie McDermott, the author of “Southern Cakes: Sweet and Irresistible Recipes for Everyday Celebrations”

For the batter:
6 tablespoons (¾ stick butter)
½ cup milk
1 cup flour
1 ½ teaspoons baking powder
¼ teaspoon salt
2 eggs
¾ cup sugar
½ teaspoon vanilla extract

For the topping:
6 tablespoons (¾ stick)
¾ cup light or dark brown sugar, tightly packed
6 maraschino cherries
1 (20-ounce) can pineapple rings

Step 1: Heat the oven to 350˚. Place the butter and milk for the batter in a small saucepan over medium heat. Warm the mixture, stirring occasionally, until the butter melts, then transfer the mixture to a small bowl to cool.

Step 2: Meanwhile, prepare the pineapple topping. Into each cup of a 12-cup muffin pan, add ½ tablespoon of unmelted butter, then evenly sprinkle 1 tablespoon of brown sugar over the bottom. Place the pan in the oven until the butter melts, about 3 minutes.

Step 3: Halve each maraschino cherry, then cut the pineapple rings into quarters. Place a cherry half, sliced side up, in the center of each cup and lay a pineapple quarter on each side. Press the fruit gently down into the butter-sugar mixture, then set the prepared pan aside.

Step 4: Finish making the batter. In a medium-size bowl, combine the flour, baking powder, and salt, and stir the ingredients with a fork until they’re evenly blended. In a large bowl, whisk together the eggs, sugar and vanilla. Add flour mixture and stir until the flour is fully incorporated. Add the milk-butter mixture and stir well to combine the ingredients into a smooth batter.

Step 5: Pour the batter into the muffin pan, dividing it evenly among all the cups. Bake the cupcakes until they’re lightly browned, dry around the edges and pulling away from the pan a little about 25 minutes.

Step 6: Transfer the pan to a rack to cool for 5 minutes. Use a butter knife to carefully loosen each cupcake from the edges and bottom of the pan, then place a cookie sheet over the top. Invert the pan, turning the cupcakes out onto the cookie sheet, then transfer them back to the rack to cool completely. Serve the cupcakes at room temperature.

Makes 12 cupcakes.


  1. Ok, Jean, you know I'm biased! But I'm so glad you liked them. All of our recipes are tested -- and tasted by staffers -- in our test kitchen. I, however, did not get to go to this particular tasting. Harumph! But you do a great job of bringing them to life for all of us.
    Now, it's not a cupcake, but watch for a piece in the November issue. I did get to go to that tasting, and oh my, the pear frangipane pie is deadly -- good, that is.

  2. I just made these, they are in the oven right now. One thing, the part of the directions in step 4, where it says to mix egg mixture in large bowl, is that meant to mean the eggs and sugar? At first I just whisked the eggs and then added the flour mix, then the milk and butter mix, and luckily I tasted the batter and realized the sugar was missing. I added the sugar at the end. Hopefully they still come out okay. Maybe it's just me, but that was a little confusing.

  3. You're absolutely right, Autumn. It is confusing! I copied it from the magazine, but I'm going to go in and correct it. I hope you like the cupcakes! They're one of my very favorites :-)

  4. Thanks Jean! They turned out great! The thing that's so great about these as cupcakes as opposed to a cake, is you get that gooey crunchy edge part in each one. When I make a pineapple upside down cake, the edge pieces always go first, and nobody is that interested in the middle. This is a great recipe. Thanks for sharing it!

  5. The oven setting? Is that really 305? That seems both very unusual AND specific? Not 300? 315? Or 350?

  6. Summer, how can it be that we haven't caught that error before this??? Thank you so much for bringing it to my attention! I really appreciate it and I've corrected the oven temperature. (350 degrees)

  7. So Are these really cupcakes or are they really mini upside down cakes?

  8. Thanks for the recipe. Baked these for teacher appreciation week and it was a smashing success. Everyone loved it! ...I've posted the recipe on my blog and linked back to you.