To learn more about this recipe, see our related story, Smooth Operator, in our National edition.
Recipe adapted from Maura Kilpatrick, Sofra, Boston, MA
Yield: 30 cookies
Cook Time: 20 minutes
1 cup (10 ounces) pitted Medjool dates, roughly chopped
8 ounces almond paste, broken up into pieces
1½ teaspoons cinnamon
1 tablespoon orange juice
1 tablespoon grated orange zest
1 teaspoon instant espresso dissolved in 2 tablespoons water
1¾ cups all-purpose flour, plus more to work with
½ cup plus 2 tablespoons confectioners' sugar
½ teaspoon salt
2 sticks (8 ounces) butter, cold and cut into small cubes
¼ cup milk
2 tablespoons olive oil
1. Prepare the filling: In a medium bowl, combine all of the filling ingredients and fold together until moistened. Transfer the mixture to a food processor and pulse until smooth. Place the filling in a covered container and refrigerate until chilled. The filling can be made 4 to 5 days in advance.
2. Prepare the dough: In the bowl of a standing mixer, combine the flour, ¼ cup plus 2 tablespoons of the confectioners' sugar and the salt. Add the butter. Using a paddle attachment, mix on low speed until the butter is in tiny pieces.
3. In a small bowl, combine the milk and olive oil; add to the dough. Continue to mix on low speed until the dough comes together completely. Transfer the dough to a floured work surface and knead into a rectangle. Divide the dough in half, wrap each half in plastic wrap and chill for at least 30 minutes, up to 4 days.
4. Remove the dough and filling from the refrigerator and set aside to come to room temperature. Lightly flour a nonstick mat or piece of parchment paper and roll one of the dough halves into a 16-by-8-inch rectangle, with the long side closest to you. Refrigerate for 15 to 20 minutes, then spread an even layer of the prepared date filling over the dough, leaving a 1½-inch edge clear on the side farthest from you. Brush the uncovered edge with water. Starting with the side, gently begin to roll the dough away from you into a cylinder, sealing well at the edge. Roll gently to thin the log out slightly. Repeat the process with the other half of the dough. Chill the logs for 30 minutes or overnight.
5. Preheat oven to 325°. Slice the logs on a slight diagonal to ½ inch thickness. Place on a parchment-lined baking sheet and bake for 25 minutes. The cookies should remain white. Remove from the oven and let cool completely. Dust the cookies generously with powdered sugar and serve.