Make the dough

• In a large mixing bowl, cream the butter and powdered sugar just until well combined.
• Add the vanilla and mix just until combined.
• Add the flour and salt and mix just until the dough comes together; it will be soft and sticky.

Chill the dough

• Transfer the dough to plastic wrap, flatten into a rectangle and refrigerate.

Preheat the oven

• Preheat the oven to 325 °F and line two baking sheets with parchment paper.

Roll and cut the cookies

• On a floured surface, roll the dough about ¼-inch thick; if using an embossed rolling pin, stop just before ¼-inch and make the last pass with the embossed pin.
• Cut out cookies with a 2–2½ inch cookie cutter, then cut out the center with a smaller circle.
• If the dough is very soft, freeze it for a few minutes before transferring the cookies to the baking sheets; re-roll the scraps and repeat.

Chill the cookies

• Chill the cut cookies in the fridge.

Bake

• Bake for 12–14 minutes until very lightly browned on the bottoms; if your oven runs hot, stack another sheet pan underneath and bake a few minutes longer.

Cool the cookies

• Let the cookies cool on the baking sheet for 5 minutes, then transfer to a cooling rack to cool completely.
• Keep the parchment paper used for baking.

Melt the chocolate

• Melt the chocolate in a double boiler or in the microwave in 30-second intervals, stirring between each, until fully melted.
• Transfer the melted chocolate to a piping bag.

Coat the cookie bases

• On the reserved parchment paper, pipe chocolate into a circle using the imprint of each cookie as a guide.
• Place a cookie on top and move it around so the entire bottom is coated.

Add the stripes and set

• Pipe four stripes of chocolate over the top of each cookie.
• Refrigerate until the chocolate is set.