Line two large baking sheets with parchment paper and set them aside.
Add the softened butter and granulated sugar to the bowl of a stand mixer fitted with the paddle attachment. Beat on medium speed for 1-2 minutes, or until the mixture is light and fluffy.
Next, add the egg and vanilla. Mix to combine.
With the mixer on low speed, slowly add the flour. Mix just until the dough comes together into a ball around the paddle.
Scoop out 2 tablespoon-sized portions and roll them into smooth balls.
Place the balls on the parchment-lined baking sheets, making sure to place them at least 2 inches apart.
Press each ball down to form a 1/2-inch thick disc.
Transfer the cookie dough to the fridge to chill for 15 minutes.
While the dough chills preheat the oven to 350 degrees F.
Bake the cookies for 10-11 minutes or just until they are beginning to turn golden brown on the bottom.
Remove the cookies from the oven and allow them to cool completely before topping them with the ganache.
To make the ganache, add the chopped chocolate and heavy cream to a heat-safe bowl. Microwave for 1 minute and then whisk until smooth. If the chocolate hasn’t fully melted, microwave for an additional 15 seconds.
Dip each shortbread cookie into the ganache and top with crushed candy canes. Make sure to add the candy canes before the chocolate sets.
Transfer the cookies back to the fridge and chill until the ganache is set, about 20 minutes.
Enjoy immediately or store in an airtight container in the fridge for up to 3 days.