For the Cookie Dough:
1/2 cup butter, room temperature
2/3 cup sugar
1 tsp. vanilla
1 cup all-purpose flour
1/3 cup dutch process cocoa
1/2 tsp. salt
1 cup powdered sugar
1 cup semi-sweet chocolate chips
2 large candy canes, crushed
1/2 cup dark chocolate chips (or dark chocolate bar, broken into chunks)
In a stand mixer (or by hand in a large bowl) cream together butter, sugar, egg, and vanilla.
Add flour, cocoa, and salt to butter and mix until just combined.
Cover dough with plastic wrap and chill for 30 minutes to an hour.
When dough has chilled, shape it into 1 inch balls. I like to use a small cookie scoop to make sure they're all evenly sized.
Roll each ball in powdered sugar until it's lightly coated. Place 1 inch apart on a lightly greased or parchment-lined cookie sheet.
Lightly press down on each cookie with your thumb to make an indent.
Bake cookies at 350 for 9 minutes.
Remove cookies from oven and let cool on a wire rack until they're cool to the touch, about 30 minutes. If the indents in the cookies puff up in the oven, gently push them back down with the back of a spoon.
Melt semi sweet chocolate in a double boiler (or in the microwave, just be careful to stir frequently so chocolate doesn't burn) until it's smooth.
Spoon a dollop of semi-sweet chocolate into the center of each cookie.
Sprinkle a few pieces of crushed candy cane on top of the chocolate cookie centers while the chocolate is still warm. Let chocolate set for 30 minutes to an hour.
Melt dark chocolate over a double boiler (or in the microwave) until smooth.
Place melted dark chocolate in a pastry bag with a small tip. (You could also put it in a plastic bag and snip a small piece of the corner off).
Pipe dark chocolate over cookies in a zig-zag motion. Let set until chocolate has cooled and serve!
Store cookies in an airtight container on the counter for up to a week.