Gluten-Free Pineapple Upside-Down Cupcakes


I remember the first time my mom made pineapple upside-down cake. Actually, I’m sure she’d made it before – she seemed to know what she was doing – but it must have been before my time. Anyway, I was quite thoroughly impressed with the results, being a pineapple lover and a cake lover (and an anything-gooey-dessert lover), but for some reason it maintained its status as a rarity in our home.

Well, we’ve had a can of pineapple rings taking up space in our pantry for a couple years now, so I decided to try resurrecting the recipe gluten-free style.

A problem I’ve had with many gluten-free cake and quick bread recipes is a tendency to sink in the middle and/or crumble when they’re cooked in larger pans, so, having seen pineapple upside-down cupcakes on Pinterest numerous times, I decided it might be better to try that than an actual cake.

The results were successful, and quite a hit with hubby and Garrett (who refers to anything muffin-shaped merely as “cake!”)

The only drawback was having to cut down the pineapple slices to fit the muffin cups – not that Garrett and I weren’t more than happy to, ah, dispose of them. we ended up with about 3/4 of a slice squished into each cup.

Ready to try the recipe?


Gluten-Free Pineapple Upside-down Cupcakes

If you love pineapple upside-down cake, you’ll love this cupcake recipe.

  • Author: Elise




  • 1 can sliced pineapple
  • 2T. Melted butter
  • 1/2 cup brown sugar


  • 1/3 cup butter
  • 1 1/4 cup milk
  • 1 1/4 cup flour mix
  • 1/2 cup brown sugar
  • 2 t. Baking powder
  • 1/2 t. Salt
  • 1/2 cup pineapple juice
  • 1 egg
  • 1 t. Vanilla


  1. For the topping: Stir butter and brown sugar together.
  2. Grease a muffin tin and divide brown sugar mixture evenly between the 12 cups.
  3. Place one pineapple ring in Bottom of each cup. You’ll probably need to cut the ring to make it fit.
  4. Add half a marachino cherry to center of each ring if desired.

For the cake:

  1. Mix first 5 ingredients together.
  2. Add juice, egg and vanilla.
  3. Beat well. Pour into muffin tin (as prepared above).
  4. Bake at 350. For 15-20 minutes.
  5. Let cool for 10 minutes.
  6. Loosen edges of each cake with a butter knife and turn into a wire rack.
  7. The tips should be flat, which may not look the prettiest when you take them out of the oven, but since they’re going to be served “up-side down” that’s a good thing!


Did you make this recipe?

Share a photo and tag us — we can't wait to see what you've made!

Get Your Garden Cheat Sheets!

Want to know exactly when, where, and how to plant your vegetables? Sign up to get our FREE companion planting guide, and garden planting cheat sheet printable.

We won't send you spam. Unsubscribe at any time. Powered by ConvertKit

Similar Posts


  1. Please tell me how you measure flour? Do you scoop and level or do you spoon flour in cup then level. I am used to weighing Gluten free flours in grams

  2. FYi this morning I made your blueberry scones and I actually spooned then leveled. they turned out great ,

  3. These are delicious! No one in my family could even tell that they were gluten free. I will definitely be making them again.

Leave a Reply

Your email address will not be published. Required fields are marked *

Recipe rating 5 Stars 4 Stars 3 Stars 2 Stars 1 Star