Chocolate Truffle Peppermint Kiss Cookies {gluten free}

When I worked in the corporate arena I always remember unending plates of homemade holiday treats floating around the office.  They seemed unstoppable.  Though they were delicious and made with time and care by different employees, it was not something I truly appreciated until becoming gluten free.

Of course being gluten free does not stop one from making holiday cookies, but generally holiday cookie events do not cater to those who dine ‘sans’ gluten.  Our local CSA (Celiac Sprue Association) chapter hosts an annual event that really amplified the glory of the holiday cookie for me.  A few years into being gluten free we came upon this holiday cookie exchange event that was exclusively gluten free.  Having no idea what to expect but loving a good holiday outing, we whipped up a batch of Peppermint Bark or Gender-Neutral Gingerbread People, printed out the requisite 2 dozen copies of the  recipe, grabbed two empty food storage containers and set on our way.

The exchange is held in the neighboring town of Niwot, originally a farming town with a charming downtown (about 3 blocks long), with little shops and restaurants.  The cookie exchange is held in the Grange which for those not from a more rural area is like a town hall where communities would gather.  Much to our delight several large tables were set up all festooned with gorgeous cookies and confections from home bakers and some professional gluten free bakeries in the area.  Mulled cider and coffee were served and people gathered to meet for the first time, catch up with those they already knew and eat endlessly with everything present being ‘safe’ for those gluten free.  My children were over the moon as you might imagine after practicing gluten-navigation in their daily lives whenever food is near!

This fond tradition gave way to trying something on my culinary bucket list.  I’ve never, ever baked a cookie with M & M’s or a big candy kiss in them and decided this would be the year.  I merged a few of my recipes to create this Chocolate Truffle Peppermint Kiss Cookie.  It is a moist, chewy, rich, chocolately cookie with a striped candy cane kiss in the middle.  Easy, delicious and a perfect way to get the holiday juices flowing for baking to come!

Chocolate Truffle Peppermint Kiss Cookies

Prep Time: 30 minutes

Cook Time: 12 minutes

Total Time: 1 hour

Yield: 24 cookies

Being my first attempt at candy Kiss topped cookies, I received a lesson in patience. I waited about 2 ½ minutes, left the cookies on the baking sheet and pushed the flat end of the kisses vigorously into the cookie. They looked great….for about 3 more minutes until they slowly melted into little festive striped pools like snowmen on a sunny day! Don’t jump the gun; waiting a bit longer, removing the cookies from the baking sheets and gently placing the Kiss on the cookie worked perfectly!


  • 6 tablespoons Gluten Free flour mix (OR all purpose flour if not gluten free)*
  • ¼ teaspoon Baking Powder
  • ¼ teaspoon Kosher Salt
  • 1 ½ cups plus 1/3 cup quality Semi-Sweet Chocolate Chips
  • 2 tablespoons unsalted Butter
  • 2 large Eggs, room temperature
  • ½ cup granulated Sugar
  • 1 teaspoon Vanilla Extract
  • 24 Candy Cane Kisses, unwrapped (I used Hershey’s brand)


  1. Preheat oven to 350 degrees. Prepare two baking sheets with a silpat or parchment paper.
  2. In a small bowl, combine the flour, baking powder and salt. Stir to fully mix and set aside.
  3. Using a double boiler, a metal mixing bowl over a saucepan of boiling water OR the ‘melt’ function of a microwave, combine 1 ½ cups of the chocolate chips and the butter and place in the appropriate bowl for your melting method. Heat until fully melted, stirring as needed, until smooth texture.
  4. In a medium mixing bowl combine the eggs and lightly beat with a whisk or mixer. Add sugar and vanilla extract, mixing until fully combined.
  5. Add melted chocolate mixture to butter-sugar-vanilla and stir to fully combine.
  6. Gradually stir in dry ingredients to fully combine and add the remaining 1/3 cup of chocolate chips, stirring to incorporate.
  7. Place tablespoon amounts of the cookie dough on the prepared baking dishes with 2 inch spacing in between them. Bake for 10 minutes and check for doneness (the cookies will have some cracks in them, be glossy but not dry; do not overcook); if still too soft allow to bake a few more minutes. Note: I found different baking pan types make a difference of a few minutes in the baking duration.
  8. Allow cookies to cool about 5 minutes on the baking sheet, remove and place on cooling rack. Gently place a candy Kiss in the center of each cookie, ensuring full contact of the bottom of the kiss and the top of the cookie; do not push the Kiss into the cookie. The heat of the cookie will gently melt the bottom of the Kiss to the cookie and when fully cooled they will be adhered.
  9. Store any uneaten cookies in a sealed food storage container (refrigerated if over a few days).


*I use home blended gluten free flour mixes or King Arthur’s Gluten Free Flour Blend which seems the most similar to all purpose flour in texture and flavor.

Last week I introduced you to Udi’s Gluten Free Living Community of which I am now a Community Leader.  An uber cool feature of the community is the ability to embed conversations into blog posts.  I started a conversation in the community soliciting gluten free holiday cookie recipes to share for virtual gluten free Holiday Cookie Exchange.  You too can ‘hop in’ and share any favorite recipes you might have.  Click on the conversation box, share your thoughts and recipe, hit ‘Reply’ and ‘join the conversation’!


  1. Robin D. Perera says

    Dear Toni,
    Oh my, your chocolate truffle peppermint kiss cookies look so festive and yummy!
    I have been making peanut butter cookies with Hershey”s kisses forever, and my 4 sons (ages 14, 19, 21, & 23) always request my brownies with cream cheese frosting and crushed peppermints at the holidays.
    Now, I will add your cookies to my repertoire.!
    The red striped candy kiss looks fabulous -it lends such a cool yet minimal elegance to the chocolate cookie.
    I was happy to see recently how the red & white striped paper straws from my youth have made a comeback.
    I love how you styled your gorgeous cookies with them!

    I have so enjoyed reading your blog the past year or so here in Sherborn, MA
    Thank you!

    • Toni Dash says

      Your selections sound delicious Robin! I’m honored to have these cookies served in their midst! I so appreciate your lovely comment and am honored you spend your time on my blog. Thanks you so much. Happy Holidays to you and your family!

  2. says

    These look terrific! Looks like a pretty easy recipe, great flavor, and the peppermint kisses are such a nice garnish! Great tip about not being impatient, and letting the cookie cool a bit before placing the kisses. I’m sure they still tasted great when melted, but the decorative effect was a little lacking!

  3. Patti Smith says

    Planning to make these cookies today. I assume the melted chocolate is added in step 5. Read the recipe several times and maybe missed it. That is what I will do when I make them. Looking forward to tasting them.

    Patti Smith
    Burnsville, NC

    • Toni Dash says

      Holy mole Patti! You are absolutely right; step 5 dropped out of the recipe. It’s back now thanks to your prompt! So sorry for any inconvenience! Let the baking begin!

    • says

      Hi Angel. This is the amount of flour I’ve always used, 6 Tablespoons, when making this recipe and you can see the results in the photos. If your batter seems way too runny (this does not make a thick cookie batter) you can always try adding 1-2 more tablespoons of flour if you feel the consistency works better. I would guess the fat content in different types of chocolate can affect the thinness of the batter too. Please let me know how it works out for you! Are you baking at altitude or sea level?


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