Chocolate Gooey Filled Peppermint Cupcakes, Gluten Free

Chocolate Gooey Filled Peppermint Cupcakes, Gluten Free & Dairy Free. I hope you have more in the kitchen!

Think of these peppermint gooey filled chocolate cupcakes as a fond holiday farewell to Hostess.  Holiday nostalgia, right? But really, the only thing these Chocolate Gooey Filled Peppermint Cupcakes have in common with Hostess is the fact that they are both gooey filled. One of these things is not like the other – it’s much tastier.  No one would be unhappy getting one of these cupcakes as a gift. Or finding one on a tray at a holiday gathering. They may want the entire pan, actually.

These began as a simple chocolate cupcake and grew to become something slightly over-the-top-better. But hey, the holidays can be over the top. After all, when else is it reasonable to buy bags of green and red candy on purpose? Next to never, right?

Nothing in the recipe requires any magical baking skill. The cupcakes are easy – just don’t skimp on the peppermint extract. It will seem like too much at first but the perfume and flavor mellow just as you finally wash it out of your hands and hair.

And don’t fret about getting the filling into the cupcake. If you can’t pipe it in, just use the drill & fill method, otherwise known as scooping out some cake and replacing it with filling. Neatness doesn’t even matter because the fluffy buttercream will hide all kinds of cupcake-filling construction challenges.

If you do pipe the filling, fair warning – the first cupcake usually gets sacrificed as you gauge just how much gooey stuff should go in before it bursts apart. But no worries. I guarantee you will want to eat that first overfilled cupcake yourself – if for no other reason than to stop drooling. You know. In the name of neatness and all. In any case you don’t want a messy blown up cupcake on the plate, right?

What are you reading this for? Go. Get baking. Chocolate Gooey Peppermint  filled Cupcakes await. All you need is a couple of hours including all the cooling-your-heels time and this decadent holiday goody can be yours or yours to share. Should you wish. Probably a good idea. You know, the nice-list.

Happy almost holiday.

Chocolate Gooey Filled Peppermint Cupcakes, Gluten Free & Dairy Free. Mine!

Chocolate Gooey Filled Peppermint Cupcakes, Gluten Free
Chocolate Peppermint Cupcakes
  • 130 grams AP GF flour (66 grams superfine brown rice flour plus 32 grams each superfine white rice flour and tapioca flour/starch) (1 cup)
  • 186 grams granulated sugar (scant 1 cup)
  • 30 grams unsweetened good quality cocoa (1/3 cup)
  • 1 scant teaspoon baking powder
  • ½ teaspoon instant espresso powder
  • ½ teaspoon kosher salt
  • 96 grams solid vegetable shortening (Spectrum) in pieces (8 tablespoons)
  • 3 extra-large eggs
  • 140 grams almond milk (very scant ⅔ cup)
  • 1 teaspoon vanilla
  • 1 teaspoon pure peppermint extract
Gooey Filling
  • 196 grams solid vegetable shortening (Spectrum) (1 cup)
  • 220 grams powdered sugar, sifted (2 scant cups)
  • 2 tablespoons AP GF flour
  • 120 grams canned full fat coconut milk (1/2 cup)
  • 1 teaspoon vanilla extract
Peppermint Buttercream
  • 96 grams solid vegetable shortening (Spectrum) (8 tablespoons)
  • 325 grams powdered sugar, sifted (about 3 cups)
  • 1 teaspoon pure peppermint extract
  • 1 teaspoon vanilla
  • 1-3 tablespoons warm water
  1. Preheat oven to 350. Place cupcake liners in a muffin pan (about 12-14 total). Set aside.
  2. In a large bowl whisk together flour, sugar, cocoa, baking powder, espresso powder, and salt. Add in shortening pieces, eggs, almond milk, vanilla and peppermint extract. Using a handheld (or stand) mixer on medium/low combine until batter is smooth, lump-free and a little bit fluffy, about 2-3 minutes. Fill each liner just shy ⅔ full. Bake 18-22 minutes though it might take a minute more or less. Remove from the oven when a toothpick comes out without crumbs. Cool for a few minutes. Remove cupcakes to a rack and cool completely before adding filling and buttercream.
Gooey Filling
  1. Place all the ingredients in the bowl of a stand-mixer. Using the paddle attachment, mix on low-speed until all the ingredients are combined. Scrape down the sides as needed. Turn the speed to medium-high and keep mixing for a few minutes. The filling will start out looking almost curdled and then turn satiny smooth and fluffy. When the cupcakes are cool, use a chopstick and poke a hole in the top and rough up the insides a bit. Using a plain filling piping tip (it's long and skinny) pipe filling into the hole until it begins to come out the top. You'll get an idea when to stop. You may have to sacrifice one cupcake to know (one for the baker). Alternatively cut out a cylindrical plug in the cupcake and fill, adding back a cupcake cap. The buttercream will cover all kinds of construction.
Peppermint Buttercream
  1. In the bowl of stand-mixer or using a hand-held mixer whip together shortening, sifted sugar, vanilla, peppermint and 1 tablespoon of warm water. Whip mixture until it is very light and fluffy. It is seems too stiff, add a tiny bit of warm water at a time. Pipe onto each cupcake.
  1. Top with a candy cane kiss or chocolate kiss

Chocolate Gooey Filled Peppermint Cupcakes, Gluten Free & Dairy Free. You might need a spoon...


  1. Please tell me you can sub butter every time solid vegetable shortening is listed. Same measurements?

    • GlutenFreeCanteen says:

      Hi Tori – I think that would work. I’m not sure that it would work for the filling, though. I haven’t tried it with butter. I use Spectrum organic shortening, if that helps. For the cupcake, I’d add a tablespoon more butter. For the buttercream, the same. And the filling is an experiment you’ll have to try. Hope that helps.

  2. I have tried this recipe twice and neither time has the cake turned out well AT ALL. The shortening does not meld with the batter, the bottoms of the cupcakes are filled with grease when I take them out, and the cake ends up spongey. Please tell me that someone else has had this problem. Is there a reason that shortening is used in the batter instead of something else, say canola oil?

    • GlutenFreeCanteen says:

      Hi Catherine – to trouble shoot a recipe, first compare the ingredients list to what you are using – are they all exactly the same, including the flour mix? And same with the instructions. Are you making any ingredient substitutes? Are you using an electric mixer? Are all your ingredients room temperature, including the eggs? The shortening, if room temperature, will work into the other ingredients all in one bowl as written – think of it as like a cake mix where you work in the ingredients the same way. When it is fully mixed the batter will be thick and fully combined – if any white flecks from the shortening show, then it is not mixed enough. The cake should not come out greasy but the cake will a little spongy as you see in the photo.

      We use shortening so that the whole thing is dairy-free. If you want to use butter, see the comment above. It has not been tested with butter so you’d be experimenting. I’m sorry it is not working out for you, that must be frustrating. Spectrum can be stored at room temperature. When it is cold in my house it seems a little more solid than when the kitchen is warm. Try setting it in a warm spot, but not warm enough to melt. BTW, canola oil, while used in other cake recipes on our blog is not a good substitute for the fat in this recipe – cake batter is based on ratios and a liquid fat will not work for this.

      I’m happy to go over it with you if you let me know exactly what you are using and how you are making the cupcakes – hope that helps.

      • Hi, I am using all ingredients as written including the flours and the eggs at room temperature. I stay away from dairy as I try to make all of baking allergen-friendly. I have a Kitchen-Aid stand mixer and even after beating the batter for a long period of time and trying to “smash” it against the side of the bowl to incorporate the shortening I could not get it to disappear into the batter. It stays chunky. 🙁 I have used two different tubs of the Spectrum shortening each time I tried this recipe. I think the cake on my first tub turned out better than this one. My shortening just stays in the cupboard, so it’s room temperature. I follow the recipe exactly as well.

      • GlutenFreeCanteen says:

        Thanks for getting back so quickly. Try this – use the whip attachment rather than the paddle. That should help break up the shortening a little bit better. If there are tiny little flecks of white, that would be ok because it will melt into the batter as it bakes, but large chunks will sink and that’s when you’ll see the greasy bottom. I do like Spectrum but having used a zillion tubs by now I have noticed that some are more soft than others. The one I am using right now is really solid and it does have trouble mixing in but as long as it ends up being tiny flecks, it works just fine. Sometimes I also let the batter sit for 5-10 minutes when the shortening flecks and then I whip or mix it again and by then the shortening will fully incorporate. Hope that helps.

        If the whip attachment doesn’t solve the problem, look in the index for a cupcake that uses canola or vegetable oil. There are plenty. Make the filling and icing the same as this recipe, using the whip attachment.

      • Thank you for the suggestions – if the shortening and I cannot get along, I’m sure the filling and frosting will taste great on another cake.