16 tablespoons 2 sticks unsalted butter cut into 16 pieces, room temperature
¾ cup powdered sugar
1 ½ orange zest
1 large egg (room temp)
1 large egg yolk (room temp)
1 ½ teaspoons vanilla extract
½ teaspoon sea salt
2 cups all purpose flour
For the Ganache
1 cup dark chocolate chips
¾ cup heavy whipping cream
Make sure the butter and eggs are room temperature. In a pinch you can microwave the butter for 5-15 seconds until it’s soft, but not melted. To bring eggs to room temperature-- place both eggs in a medium bowl and cover with slightly warm(not too warm!) water and let sit for 5-10 minutes until there is no chill.
Prepare 2 baking sheets with parchment paper and set aside.
In a stand mixer with the paddle attachment, mix the butter, powdered sugar and orange zest on medium for 4 minutes. Turn the mixer on low and pour in the egg, egg yolk, vanilla and salt. Mix for several minutes. The mixture will look gross but it’s fine! Finally mix in the flour and stir on the lowest setting until the dough forms.
Lay piece of parchment paper on your work surface and dust it generously with flour. Scoop the dough on the parchment, sprinkle with more flour and then roll it to ¼ inch thickness. The dough will be very sticky, so flour the rolling pin as necessary. Transfer the parchment paper with the dough onto a baking sheet and freeze for 30 minutes or refrigerate for 1 hour.
Use a 2 inch cookie cutter and cut as many cookies as efficiently as you can. Roll the scraps and cut any left over. Chill the cookies on a parchment lined baking sheet in the freezer for 15 minutes or in the refrigerator for 30 more minutes.
Preheat the oven to 350ºF.
Bake in the center of the oven for 8-10 minutes (bake time will vary based on the cookie cutter size) Let the cookies cool on the baking sheet for 5 minutes before moving to the cooling rack.
To make the ganache. Set a medium glass bowl over a medium saucepan of simmering (not boiling!) water. Add the chocolate chips to the bowl, stirring continuously. Once the chocolate begins to melt, add in the heavy cream. Whisk furiously until melted and smooth. Remove from heat and stir occasionally to stay fluid. Let the chocolate cool -- but not harden.
Once the cookies and the ganache are cooled, quickly spread a generous amount on half of the cookies and top with another cookie.