Hostess-Style Chocolate Cupcakes

gluten free chocolate cupcakes

Whew! I just finished my first year teaching at a wonderful school. There is one thing I’ve heard talking to teachers: it doesn’t matter if are teaching second grade or twelfth grade, public or private school – the first year is a doozie. And it was, but I’m hoping that I’ll have more time to share recipes with you on the blog going forward.


These cupcakes are a nostalgic treat that everyone will love. They do take some time to assemble but they are worth it. The prep is reduced by using another cake box hack, and if marshmallow fluff is available and meets your dietary requirements, you can use it instead of making your own filling. If you have some of the chocolate icing in your freezer, the assembly gets even faster.

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Yellow Cupcakes

These cupcakes were one of my first (successful!) gluten free baking attempts, and they are a great place for anyone to start. I found the recipe on A Gluten Free Guide , and it follows in the great tradition of doctored cake mixes. That’s right, these cupcakes “cheat” by using a boxed GF cake mix as a base. No tracking down multiple flours, no covering your entire kitchen in tapioca flour dust, and these things are pretty much foolproof.

The chocolate frosting recipe can be found here.

Ingredient note: This recipe calls for orange juice, which I don’t always have available (you know, for those cupcake emergencies). I keep a container of orange juice concentrate in my freezer, and scoop 2-3 tablespoons into a measuring cup, and add enough warm water to bring the total volume to the 3/4 c. required for this recipe.

Yield: 18-21 cupcakes



  • 1 package gluten free yellow cake mix (Betty Crocker brand and Gluten Free Pantry brand both work well)
  • 1 package (3.4 oz/96 g) Jello instant vanilla pudding
  • 1/4 c. sugar
  • 1/4 teaspoon salt
  • 3/4 c. orange juice
  • 1/2 c. oil
  • 4 eggs
  • 1-1/2 Tablespoon vanilla (recommended: Nielsen-Massey vanilla bean paste)


Other Equipment:

  • 2 – 12 cupcake pans
  • cupcake liners
  • #40 portion scoop (optional)
  • hand-held wish or electric mixer
  • spatula

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Chocolate Icing

This chocolate icing recipe is based on the Pioneer Woman’s  sticky chocolate icing. I scaled it up a bit since the original recipe left small amounts of sweetened condensed milk languishing in my fridge.

This batch makes enough icing to frost two batches of yellow cupcakes (recipe here). This stuff freezes well, so after frosting your cupcakes, scoop the rest of the icing into a resealable container, let it cool, and then freeze. When you make your next batch of cupcakes, just microwave the frozen icing and stir it every minute. As it softens, shorten the time between stirs to 30 seconds.


Sometimes the icing doesn’t always last until the next batch of cupcakes…


Yield: ~ 2 c. icing (enough for two batches of 18-21 cupcakes)



  • 1 – 14 oz. (396 g) can sweetened condensed milk
  • 8 oz. (226 g) semi-sweet chocolate
  • 2 Tablespoons butter

Other Equipment:

  • medium sized saucepan
  • spatula
  • small spoon

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