Preheat oven to 350F, with racks in upper and lower thirds.
In a bowl mix together flour, cocoa powder, cinnamon and salt. Set aside. In a larger bowl, using an electric mixer, beat 1 cup each of butter and sugar on medium high until light and fluffy. Add egg and vanilla mixing well. With mixer on low slowly add in flour mixture and beat to combine.
Place 1/2 cup sugar, sanding sugar or crushed candy canes on a plate. Roll your cookie dough into 1 inch balls and then roll them in sugar to coat. Place balls 1 inch apart on parchment lined baking sheets. Bake 4 minutes then remove sheets from oven and with a melon baller or under side of a round 1/2 teaspoon make an indentation in the centre of each cookie.
Put cookies back in oven and bake until they are set but still look moist (another 4 minutes). Let cool on wire racks.
In a microwaveable bowl microwave your chocolate and 1/4 cup butter in 10 second increments, stirring each time until melted. Stir in peppermint extract. Let cool until thickened. At this point you can either spoon the chocolate into the cookie indentations or put the chocolate into a plastic locking bag, snip hole in one corner and pipe chocolate into indentations.
Should last up to a week in an airtight container and makes approximately 4 dozen.