First, Make The Cookies:

1. Preheat The Oven & Prep Your Pans. Start by preheating the oven to 350 degrees F. Then, line two cookie sheets with parchment paper or silicone baking mats (I prefer parchment here).
2. Mix The Dry Ingredients. In a medium bowl, combine gluten-free flour blend, cocoa powder, baking soda, and salt. Whisk until it’s well blended and set aside.
3. Cream Butter & Sugars. In the bowl of a stand mixer (or a large mixing bowl), combine softened butter, brown sugar, and sugar. Cream 2-3 minutes, or until smooth, light, and fluffy.
4. Add Eggs & Flavoring. Scrape down the edges of the bowl, and add eggs one at a time, beating to combine fully before adding the next one. Add vanilla extract and peppermint extract and stir to combine.
5. Slowly Add Dry Ingredients & Milk. Add about dry ingredients a little at a time, and mix until almost fully combined. Add the milk and mix for a few seconds, then add the second half of the dry ingredients and mix until almost fully combined (just a little powder left).
6. Mix In Chocolate Chips. Pour in the chocolate chips and mix until just combined. The dough will be sticky, like thick brownie batter.
7. Scoop & Bake. Use a large cookie scoop (3 Tablespoon) to scoop 6 cookie dough balls onto a baking sheet. (I like to roll them smooth first for the prettiest presentation.) Bake cookies 9-11 minutes, or until the edges are set and the centers look just underdone. (I bake mine 9.5 minutes)
8. Shape & Cool. When the cookies are done baking, use a large round cookie cutter to gently coax them into perfect circles (this is just for looks!) and cool 2-3 minutes on the baking sheet before transferring to a wire rack to cool completely. Repeat until all the cookies are baked, alternating between cookie sheets each batch.

Then, Decorate Them:

1. Prep Your Decorating Station. While the cookies bake, set out a few sheets of parchment paper (or re-use the ones from baking the cookies after you’re done baking).
2. Melt The Chocolate. When all the cookies are baked and cooled, gently melt the chocolate chips in a medium microwave-safe bowl in 20-30 second increments until smooth and glossy. In another small bowl, melt the white chocolate chips and oil together.
3. Dip & Sprinkle. Dip the top of the cookies halfway into the chocolate, using the side of the bowl to scrape off some of the excess chocolate on the bottom half, then place on the parchment lined sheets to set. Sprinkle the chocolate dipped half with crushed candy cane.
4. Drizzle with melted white chocolate (use a fork to drizzle, or add the melted white chocolate mixture to a piping bag, snip off a tiny corner at the end, and drizzle). Let the cookies set completely. Store the finished cookies in an airtight container at room temperature 2 days, in the refrigerator 3-4 days, or in the freezer up to 2 months.