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Cream together softened butter and powdered sugar until light and fluffy.
Beat in milk and peppermint extract until well combined. Stir in salt.
In a separate bowl, whisk together flour, baking powder, and baking soda.
Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Dough will be stiff.
Divide dough in half, flatten each half into a disc, wrap in plastic wrap, and chill for at least 1 hour.
Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
On a lightly floured surface, roll out one disc of dough to about ⅛-inch thickness.
Cut out cookie shapes using a small round cookie cutter or a sharp knife.
Carefully transfer cookies to the prepared baking sheets.
Bake for 10-12 minutes, or until edges are lightly golden. Do not overbake.
Let cookies cool on baking sheets for a few minutes before transferring to a wire rack to cool completely.
Melt chocolate chips and shortening together in a microwave-safe bowl in 30-second intervals, stirring in between, until smooth.
Dip each cooled cookie halfway into the melted chocolate, letting excess drip off.
Place chocolate-dipped cookies back on the parchment-lined baking sheets to set.
For extra crispness, these cookies are freezer-ready! Store in an airtight container in the freezer.