Place the condensed milk, peppermint extract in the bowl of a mixer.
Add half of the powdered sugar and beat with a mixer on low speed. Gradually add the remaining powdered sugar. Beat until a smooth dough forms.
Sprinkle powdered sugar over a piece of parchment paper, Place the dough on the parchment and sprinkle powdered sugar over the top.
Place another layer of parchment paper over dough.
Roll dough into a 1/2 inch thick circle.
Using a 2 inch round cookie cutter, cut out circles from the dough.
**quick note: if the dough doesn't roll out evenly, place the dough in the freezer for 5 minutes to firm up, then try again.
Transfer the peppermint rounds to a parchment lined baking sheet. Freeze for 10-15 minutes.
Chop chocolate into 1/2 inch pieces. Place in glass bowl, along with shortening.
Pour 2 inches of water in the bottom of a 2" saucepan. Place chocolate bowl over water in saucepan.
Simmer saucepan over a medium flame. Stir continuously until chocolate and shortening has melted.
Using a fork, dip the patties one by one in the chocolate. Place on a piece of parchment lined baking sheet. Add crushed candy canes immediately. Let cool completely.
Store in an air tight container in the refrigerator.