To make the cookie dough: In a stand-up mixer with the paddle attachment, beat the butter and powdered sugar until it is light and fluffy. Add the cocoa powder and beat once more, scraping down the sides as needed. Next, add the egg yolk, vanilla extract, peppermint extract and salt. Add the all-purpose flour and mix just until the batter is mixed and you no longer see speckles of flour. The dough may be a bit crumbly and that’s ok!
Turn the dough out onto a lightly floured surface and divide it into two balls. Flatten those balls into disks and wrap them tightly in plastic wrap. Transfer to them to the fridge to rest for 1 hour.
Preheat oven to 375 degrees F. Remove the first disk of dough from the fridge and roll it out onto a floured work surface and floured rolling pin. The thickness should be about 1/8-inch. Stamp out cookies using a 1 1/2-inch cutter or whatever shape you like. You’ll end up with scraps, recombine them, roll it out and stamp out more cookies. Transfer the cookies to a parchment-lined baking sheet and bake for 7 to 8 minutes. Repeat with the second disk of dough. Remove the cookies from the oven and allow them to cool on the baking sheet for 5 minutes and then transfer to a cooling rack.
To make the chocolate topping: While the cookies are baking and cooling, nestle a stainless steel bowl or glass bowl atop a saucepan filled with a few inches of water. Place the whole contraption over medium-low heat. Add the chocolate to the bowl and slowly melt, stirring occasionally until very glossy and smooth. Stir in the peppermint extract.
Dip the cookies into the chocolate (using a fork) and allow the chocolate to drain off. Transfer to a parchment-lined baking sheet (I used the same parchment I baked the cookies on). Top with a few pinches of crushed candy canes. Repeat until you’ve worked through all of the cookies. Place the baking sheets in the fridge or freezer to set.
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