Makes about 2 dozen cookies
For the dough
1 1/4 cups butter, at room temperature
2 cups powdered sugar
1 cup dutch processes cocoa or dark cocoa powder (I used Hershey's Special Dark Cocoa)
1/2 tsp. salt
1 tsp. vanilla
1 3/4 cups flour
For the filling:
5 or 6 peppermint candy canes
3/4 cup butter
1 tsp. vanilla
3 cups powdered sugar
milk or cream as needed (around 1/4 cup)
In a stand mixer, with a cookie paddle attached, cream the butter and sugar together on medium speed until the mixture is light and fluffy, about 2 minutes. Add the cocoa powder, salt, and vanilla and mix until incorporated. Add half of the flour and mix. Add the remaining flour, 1/4 cup at a time until you get a pretty dry dough. Don't be worried if the dough is a bit dry...we want a cookie that doesn't spread when baked and is crispy! Divide the dough in half and pat together to form a disk. Cover the disks in plastic wrap and refrigerate for about 15 minutes.
Preheat your oven to 350 degrees. Remove plastic from one disk and roll your dough out between two pieces of parchment paper or on a lightly floured surface until it is about 1/4 of an inch thick. Use a 2 inch circle cutter to cut out the cookies. Place on a cookie sheet and bake for 8-9 minutes. It's super hard to tell when a near black cookie is done. I baked mine for 10 minutes the first round and they tasted burnt on the bottom, so you'll need to adjust as you go. Repeat with the rest of the dough. Place the cookies on a wire rack to cool.
While the cookies are cooling, prepare the filling. In a food processor or blender process the unwrapped candy canes until you have a very fine candy cane dust. Add the candy cane dust to the bowl of your stand mixer. Add the butter, vanilla, and half of the powdered sugar. Beat on medium-high speed until well combined and fluffy, about 2 minutes, scraping down the sides as needed. Add the remaining cup and a half of powdered sugar and combine. Add milk or cream as needed to get a very thick, but spreadable filling. Put the filling into a pastry bag with a large circle tip.
When the cookies are cooled, match them with a mate according to size. Take one cookie and pipe a circle of filling, about the size of a quarter, in the center on the flat bottom of the cookie. Take the mate and place it on top (flat sides together) and press it until the filling comes to the edge of the cookies. When the filling was squished to the edge of the cookie it was a little under a half inch thick. Repeat with the remaining cookies.
Serve with lots of cold milk.
These are excellent served and eaten cold. I love these straight out of the fridge.
If your world is crazy like mine and 3 hours instead of 15 minutes pass before you get back to baking, let the dough rest at room temperature for 15 to 30 minutes. The butter makes the dough super stiff if it's too cold.