Makes about 2 dozen cookies.
Note: This dough must be prepared in advance. Candied orange peel can be found in the baking aisle of most supermarkets. Substitute the freshly grated peel of 1 orange for candied orange peel. Espresso powder, such as the Medaglia D’oro brand, can be found in the coffee aisle of most supermarkets. From Elizabeth Davis of Wayzata.
• 1/2 c. (1 stick) butter, at room temperature
• 1/4 c. granulated sugar
• 1/4 c. packed light brown sugar
• 1/4 tsp. baking soda
• 1 egg
• 1 tsp. vanilla extract
• 1/2 tsp. salt
• 1 3/4 c. flour, plus extra for rolling dough
For fig filling:
• 1 c. diced dried figs
• 1/2 c. finely chopped pitted dates
• 1/2 c. freshly squeezed orange juice
• 1/3 c. diced candied orange peel (or freshly grated peel from 1 orange; see Note)
• 2 tbsp. granulated sugar
• 1/4 tsp. ground cinnamon
• 1/3 c. finely chopped walnuts
• 1 c. dark chocolate chips
For mocha ganache:
• 1 c. dark chocolate chips, divided
• 1/2 c. heavy cream
• 1 tsp. espresso powder
To prepare dough: In a bowl of an electric mixer on medium-high speed, beat butter for 1 minute. Add granulated sugar, brown sugar and baking soda, and beat until light and fluffy, about 2 minutes. Add egg, vanilla extract and salt and mix until thoroughly incorporated. Reduce speed to low and slowly add flour, mixing until just combined. Divide dough in half, form each half into small rectangles, wrap each rectangle in plastic wrap and refrigerate at least 3 hours.
To prepare fig filling: In a small saucepan over medium-high heat, combine figs, dates, orange juice, candied orange peel (or freshly grated orange peel), sugar and cinnamon. Bring to a boil, then reduce heat to medium-low and simmer until mixture is soft and thick, about 5 to 8 minutes. Remove from heat and stir in walnuts. Set aside to cool to room temperature. Once cooled, stir in chocolate chips.
To assemble cookies: Preheat oven to 375 degrees and line baking sheets with parchment paper.
Remove dough from refrigerator and allow it to rest for 10 minutes.
On a lightly floured work surface using a lightly floured rolling pin, roll one of the rectangles into a 10- by- 8-inch rectangle.
Cut each rectangle into two 10- by 4-inch strips. Portion 1/4 of the filling down the center of each strip. Lift one long side of the dough up and over the filling, and repeat with the opposite side to enclose the filling (fold dough as if folding a business-size letter). Pinch the 2 sides together at the edges. Carefully transfer the roll to the prepared baking sheet, placing them seam side down. Repeat with second strip of dough, then repeat entire process with second rectangle.
Bake until lightly browned, about 12 minutes. Remove from oven, cool for 2 minutes, then slice each strip into 1-inch pieces, cutting diagonally. Transfer cookies to a wire rack to cool completely.
To prepare mocha ganache: Place chocolate chips in a medium bowl. In a small saucepan over medium heat, bring cream to a boil and stir in powdered espresso. Pour cream mixture over 3/4 cup chocolate chips and stir until smooth, adding more chips, if necessary, to reach desired consistency Allow ganache to cool until it has thickened but remains liquid. Using a spoon, pour ganache over cookies, allowing ganache to drip down sides. Place on a wire rack for ganache to set.