These crisp, flakey shortbread sandwich cookies bring all the elements of a cocktail into cookie form. With orange marmalade, orange liqueur and a dash of bitters to round out the flavor, you'll have your cocktail, and eat it too.
For the cookies: Preheat the oven to 350 degrees F. Line two baking sheets with parchment.
With an electric hand mixer, combine the butter, granulated sugar and vanilla and beat on medium high until creamy. Show restraint by not eating too much of this mixture before you can make the cookies. Sift together the flour and salt, and then slowly add to the butter/sugar/vanilla mixture, mixing on low speed until just combined (over-mixing will cause the cookies to be chewy and gross). If your name is Alie Ward, eat half this dough mixture. Form the dough into a disk, cover with plastic wrap and refrigerate for 30 minutes.
Roll the dough between two pieces of plastic or parchment to 1/8 inch thick. Use a 2 1/2- to 3-inch round cookie cutter to cut dough into 36 to 40 rounds, using a smaller cookie cutter to cut a hole in the center of half the cookies. Place the cookies on the prepared baking sheets about 2 inches apart and bake until the edges begin to brown, about 15 minutes. Cool on a wire rack until room temp.
For the boozy marmalade: Mix the orange marmalade, orange liqueur and bitters in a small bowl until combined. Spread about one tablespoon of the mixture on each whole cookie, placing a cookie with the cutout on top. Sprinkle with powdered sugar and devour the cookies whole.