Add 2 tbsp chocolate syrup to a small plate. Add crushed candy canes to another small plate.
Dip the rim of the coffee mug into the syrup, and then the crushed candy canes.
Place the mug under the coffee dispenser. Brew a 2-ounce espresso into the mug.
Add the remaining 2 tbsp chocolate syrup, granulated sugar, and peppermint extract. Stir.
Add the milk to a frother and blend on a latte, steamed milk, setting.
Pour the milk over the chocolate peppermint coffee. Top with whipped cream, more chocolate syrup, crushed candy canes, and add one whole candy cane. Enjoy!