Gluten Free Pineapple Upside Down Cupcakes

Who doesn’t love pineapple upside down cake? A fancy way to make a big impression if you have a party, and a comforting sweet taste that takes you back to, long hot summer days as a child. There is something very unique about this sweet treat. Perhaps it’s the ability to transport you to a sun soaked beach even in the middle of the Midwest winter.

When I was living in Alaska, this was one of the first (at the time only) baked goods that a small café made gluten free. It was like spotting an island when I had been stranded in a boat on the ocean. Since then it has been one of my favorite things to enjoy, especially on those dark and cold winter nights in Alaska.

Now that it’s summer, it seems like the perfect food to add to a BBQ. Below is the recipe I used to create this scrumptious Pineapple Upside Down Cupcakes.

It’s so good you might just decide to make it your wedding cake!



  • 4 eggs
  • 1 1/3 cup white sugar
  • 8 Tbsp pineapple juice
  • 1 1/3 cup Pamela’s Gluten Free flour
  • 2 tsp baking powder
  • 1/2 tsp salt


  • 1/2 cup butter (1/2 stick or 4 Tbsp)
  • 1 1/3 cup brown sugar (packed)
  • 2-can pineapple rings
  • 6-Black Cherries halved

The Creation of Pineapple Upside Down Cupcakes

  1. Preheat the oven to 350 degrees
  2. In a medium bowl add white sugar, eggs and pineapple juice. Beat for two minutes.
  3. In another bowl sift flour, baking powder, and salt. Combine with wet ingredients stirring for 2 minutes and set aside.
  4. In a sauce pan melt the butter and brown sugar together
  5. Add some of the brown sugar butter mixture to the bottom of the cupcake pan.
    Then place a pineapple ring on top of it and add half a cherry into the center.
  6. Pour in the batter until ¾ full and then bake for 20 minutes (25 minutes if you are using a giant size cupcake pan). Check to see if they are done with a tooth pick.
  7. Remove from oven and let cool for 5 minutes. Then run a knife around the edge of each cake.
  8. Take a cooling rack and place it over the cupcake tin. Flip upside down. You may need to tap on the top in order for them to be freed.
  9. Let cool and enjoy 😀








Author: theredheadedwheatlesswanderer

I am a writer, photographer and travel of the world.

One thought

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s