I bet you thought “Milano” was just a random name bestowed by Pepperidge Farm, but the cookies—at least the homemade version—really do have an Italian background. The recipe for the pale, crispy cookie wafers is based on a traditional recipe called ossi dei morti, or “bones of the dead.”
Want to make these in another flavor? Substitute orange, almond, or your favorite extract for the peppermint in the melted chocolate. Or just leave the chocolate plain for the original version.
YIELD: about 18 to 20 sandwich cookies
TOTAL TIME: 2-1/2 hours including resting time
DIFFICULTY: 2
SPECIAL EQUIPMENT: stand mixer, pastry bag (or zip-top bag) with large round piping tip
COOKIES
1-1/4 cups (5-3/8 ounces) unbleached all-purpose flour
1/2 teaspoon baking powder
1/8 teaspoon kosher salt
3 large egg whites
8 tablespoons (4 ounces) chilled unsalted butter, cut into 1/2-inch cubes
1 cup (4 ounces) powdered sugar
1/2 teaspoon vanilla extract
CHOCOLATE FILLING
4 ounces semisweet chocolate, coarsely chopped (a scant ⅔ cup)
1/4 teaspoon peppermint extract
MAKE THE COOKIES:
Preheat the oven to 300°F. Line 2 large baking sheets with parchment paper or Silpat liners.
Whisk the flour, baking powder, and salt together in a medium bowl. Set aside.
Whisk the egg whites by hand in a separate small bowl for about 30 seconds, until bubbly, frothy, and slightly thickened but still liquid.
In the bowl of a stand mixer fitted with the paddle attachment, beat the butter and sugar together starting on low speed until the butter coats the sugar, then on medium speed for about 2 minutes until the butter is pale and creamy. Scrape down the bowl and add the egg whites in thirds on low speed, making sure each addition is fully incorporated before drizzling in more. Scrape the bowl again, add the vanilla, and stir to incorporate. There will still be a few small chunks of butter visible. Add the dry ingredients and stir until combined into a thick, whipped batter.
Fit a pastry bag or gallon-size zip-top bag with a large round piping tip and fill the bag with batter (see How to Fill a Pastry Bag, page 187). Form each cookie directly on a prepared baking sheet by piping a line of batter about 2-1/2 inches long, then reversing directions—still piping—to make a second line, forming a “U” with long edges touching. Space the cookies about 1-1/2 inches apart, since they’ll spread slightly. Because the batter is thicker than a typical frosting or filling, it may take a few tries to get into the rhythm of piping, and you may need to squeeze lower on the bag—closer to the piping tip—than you normally would.
Bake for about 15 to 18 minutes, until the cookies are no longer puffy and glossy and are just turning golden brown at the edges. The cookies will still be a little soft, but they’ll crisp as they cool. Transfer the cookies to a wire cooling rack to cool completely.
FILL THE COOKIES:
When the cookies are cool, melt the chocolate in a small, heavy-bottomed saucepan over low heat, stirring constantly with a silicone spatula until smooth. Remove from the heat and stir in the peppermint extract.
Dip the flat (bottom) side of a cookie in the melted chocolate, or brush on chocolate using a silicone pastry brush; top with another cookie, flat side down, to make a sandwich. Repeat with the remaining cookies. Allow the chocolate to firm up for at least 1 hour before serving the cookies.
Store at room temperature in an airtight container for up to 3 days.