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Pineapple Upside Down Cupcakes

The first cake I ever made all by myself was pineapple upside down. It wasn’t from scratch or anything (a boxed mix instead), but to six year old me it was one of the best cakes ever. It’s still one of my favorite cakes to make. I mean, what’s more easy and fun than just dumping a cake pan upside down and presto. . . it looks nice and is ready to serve. And honestly, anytime I can get out of frosting a cake, I’m all for it.

Saturday, with our family reunion going on I needed one more dessert, and there happened to be a box of yellow cake mix sitting in the cabinet just calling my name. So, with a quick trip to the grocery store to buy pineapple rings and maraschino cherries, I set to work making pineapple upside down cupcakes. Surprisingly, it took me over three hours to make them, but it shouldn’t take you anywhere near as long. I was the official driver for guided tours on Saturday and had to put the cupcake batter in the refrigerator a few times to ride people through the woods on a golf cart. It was a real adventure for us all and a lot of fun, and the cupcakes did eventually get made.

1 box of Yellow Cake Mix
1 tsp vanilla extract
1 can of pineapple rings
1 jar of maraschino cherries
Brown sugar
Melted Butter
Cupcake liners
Muffin pan
Parchment paper

1) In a large bowl, prepare the cake mix according to the directions on the box. Add the vanilla extract to the batter, and mix it in well. You can add pineapple juice if you want instead, but for some reason, I’ve always liked a plain yellow cake with vanilla for pineapple upside down cake – I know, I’m an oddball, but that’s just me :). Anyways, set the cake batter aside for now.

2) Spray the muffin pan with a baking spray or use butter to grease it. Pour about a teaspoon or less of melted butter into each well of the muffin pan. Then, sprinkle about half a teaspoon of brown sugar into each well on top of the melted butter.

3) Since the pineapple rings were much too large to fit into the bottom of each well of my muffin pan, I cut them into small bite-sized pieces. I placed three or four pieces into each well. Then, I sliced the maraschino cherries in half and placed a cherry half into each well with the cut side facing up. I only ended up using 12 cherries from the jar in all.

4) Then fill each well of the muffin pan about 3/4 of the way full. Bake in preheated oven according to the directions on the cake mix box, but make sure to keep a close eye on the cupcakes as they may not take as long to get done as the box indicates. I think mine only took about 20 minutes in a 350 degree oven.

5) Once, the cupcakes are out of the oven let them cool in the pan for about 5-10 minutes, then flip them out of the pan onto a large piece of parchment paper. Allow them to cool, then place the cupcakes in cupcake liners and serve.

This recipe made 24 cupcakes in all for me, but unfortunately, I don’t have any pictures of the finished ones to share. I was going to take pictures of the leftover cupcakes, but, uh, there weren’t any. It makes you feel good when people enjoy your efforts that much. These are definitely going on my repeat list, and when I make them again I’ll be sure to take a picture and update this post.

Updated on October 11, 2012:
I finally made these again a couple of weeks ago and managed to get a picture this time:

A good idea (and something I’m going to try next time), suggested by hennotrooster on Backyardchickens, is to use crushed pineapple instead of pineapple rings.

2 thoughts on “Pineapple Upside Down Cupcakes

  1. Beautiful! I’m trying this for Thanksgiving. They are in the oven now. Wish me luck 🙂

    1. Good luck and hope you enjoy them as much as we did. Have a Happy Thanksgiving!

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