- Finely chopped chocolate (both semisweet and bittersweet) may be replaced with chocolate chips.
- You may have some leftover dulce de leche—refrigerate it in an airtight container or zipper-lock back and reserve for another use.
- Even though the cookies are refrigerated to set the chocolate, they should be served at room temperature.
- For the Cookies:
- 1 tablespoon brandy or cognac
- 2 teaspoons instant coffee
- 3/4 teaspoon almond extract
- 1/2 teaspoon pure vanilla extract
- 6 ounces (12 tablespoons) unsalted butter, softened
- 2/3 cup sugar
- 1/2 cup confectioners’ sugar
- 1/2 teaspoon finely grated orange zest
- 2 large eggs, at room temperature
- 4 teaspoons honey
- 1 cup all-purpose flour, plus additional for shaping dough
- 1 cup cake flour
- 2 tablespoons cocoa powder
- 1 teaspoon baking powder
- 1/4 teaspoon salt
- For the Filling:
- 2 (13.4-ounce) cans dulce de leche (see notes)
- For the Coating:
- 12 ounces semisweet chocolate, finely chopped (See Notes)
- 4 ounces bittersweet chocolate (60% cacao), finely chopped (See Notes)
- 2 tablespoons vegetable shortening
For the Cookies: In small bowl, combine brandy, coffee, almond extract, and vanilla. Set aside.
Beat butter, sugar, confectioners’ sugar, and orange zest on medium speed until light and fluffy, about 2 minutes. Add eggs, one at a time, beating well after each addition. Add honey and coffee mixture and beat just until combined, scraping sides and bottom of bowl with rubber spatula as needed.
Sift flour, cake flour, cocoa powder, baking powder, and salt over butter mixture and combine with rubber spatula until dough comes together. Press plastic wrap directly onto dough and refrigerate for 30 minutes.
Adjust oven rack to middle position and preheat oven to 350°F. Line 2 rimmed baking sheets with parchment paper.
Once chilled, lightly coat fingers with flour and scoop 1-tablespoon portions of dough onto prepared baking sheets and pat down to about 2 1/2 inches in diameter (thickness will be about 1/4 inch).
Bake cookies—one sheet at a time—until cookies are set and appear dry on the surface, 7 to 9 minutes. Transfer sheets to cooling rack and cool cookies until cool enough to handle, about 5 minutes. Transfer cookies directly to cooling rack and cool completely, about 15 minutes.
For the Filling: Once cooled, spread half the cookies with 1 heaping tablespoon dulce de leche. Cover with remaining cookies.
For the Coating: Melt semisweet and bittersweet chocolate and shortening in large metal bowl set over pot of simmering water (bottom of bowl should not make contact with surface of water). Stir with rubber spatula until chocolate is smooth and melted. Alternatively, combine chocolate and shortening in large bowl and microwave 1 to 2 minutes until mixture is smooth, stopping microwave every 20 seconds to stir.
Line 2 baking sheets with parchment paper.
Carefully drop one sandwich cookie into the melted chocolate. With soup spoons, gently turn cookie to coat. Transfer cookie to prepared baking sheet and repeat with remaining cookies.
Transfer cookies to refrigerator and chill until set, 15 to 30 minutes.
2 rimmed baking sheets, parchment paper, electric mixer, rubber spatula, sifter, plastic wrap, cooling rack, large saucepan, large metal bowl or large microwave-safe bowl, 2 soup spoons