Pre-heat oven to 400° F.
Add candy canes to a large plastic bag and use a rolling pin or a thick glass bottle and gently roll over bag to crush candy canes into small pieces. Add to a bowl and set aside.
In a large bowl, use a hand mixer and mix soft butter, 1/2 cup of confectioner's sugar, and peppermint extract together.
Add flour and mix well with a spoon or spatula until a shaggy dough forms. Add 1/4 cup of crushed candy cane pieces and continue to mix well until a well combined, pilable dough forms. This may take a few minutes, just keep mixing.
Use your hands to roll out small dough balls and place on an ungreased baking sheet. You may need to use your hands to squeeze the dough a bit to make it more moldable. Repeat with all dough for about 24 cookies.
Bake for 10-12 minutes.
Meanwhile, add the remaining confectioners sugar to a wide shallow bowl or plate and the remaining peppermint pieces to another.
Once the cookies are done, remove them from the oven and let them cool for 2-3 minutes (make sure that you can pick them up without them falling apart. If they do start to crumble, let them cool longer). Roll each cookie in the confectioner's sugar and add to a plate. At this point, the sugar may not fully coat the cookie. Let them cool more and then give them a second roll.
After the second coat in sugar, roll top of the balls in candy cane pieces.
Enjoy!