Name: Chocolate-Dipped Cinnamon Alfajores
Cook time: P0Y0M0DT0H50M0.000S
Total time: P0Y0M0DT3H5M0.000S
Yield: about 25 sandwich cookies
Cuisine: middle-eastern
Ingredients: 1 stick (8 tablespoons) unsalted butter, at room temperature; 1/3 cup sugar; 1 tablespoon brandy; 1 tablespoon pure vanilla extract; 2 large egg yolks; 1 cup all-purpose flour, plus more for rolling (see Cook's Note); 3/4 cup cornstarch; 2 teaspoons ground cinnamon; 1 teaspoon baking powder; 1/2 teaspoon baking soda; Kosher salt; About 3/4 cup dulce de leche (from a 13.4-ounce can; see Cook's Note); 10 ounces bittersweet chocolate chips (about 2 cups)

Directions

Special equipment:

1 1/2-inch cookie cutter

Beat the butter and sugar in a large bowl with an electric mixer on medium-high speed, scraping down the sides of the bowl once or twice, until light and fluffy, about 3 minutes. Add the brandy, vanilla and egg yolks and beat, scraping the bowl, until everything is completely combined and there are no visible streaks of egg yolk.
Sift the flour, cornstarch, cinnamon, baking powder, baking soda and 3/4 teaspoon salt over the butter mixture. Reduce the speed to low and mix, scraping the bowl once or twice, until combined, about 30 seconds. Turn out onto a sheet of plastic wrap and shape into a disk. Wrap and refrigerate until firm, at least 1 hour.
Line 2 rimmed baking sheets with parchment.
Let the dough sit at room temperature until it’s just pliable but still cold, about 10 minutes. Dust the dough with flour and roll out into a 12-inch circle (about an 1/8 inch thick) on a lightly floured surface. Use a 1 1/2-inch round cookie cutter to stamp out the dough, re-rolling the scraps as you go. You should have 48 to 50 pieces total. Arrange them 1/4 inch apart on the prepared baking sheets. (This dough does not spread so they can be baked in 1 batch if arranged very close together on the 2 baking sheets.) Refrigerate until firm, about 15 minutes.
Position racks in the upper and lower thirds of the oven and preheat to 350 degrees F.
Bake, rotating the baking sheets from back to front and top to bottom halfway through, until the cookies are just beginning to brown very lightly on the bottom, 16 to 18 minutes. (Even if they don’t take on much color, it's important to not overbake them as the cookies should be very light and tender rather than thin and crisp when cooled.) Let the cookies cool for 10 minutes on the baking sheets, then transfer to a cooling rack to cool completely. (Save one of the parchment-lined baking sheets for when you dip the cookies.)
Spread half of the cookies with a 1 heaping teaspoon dulce du leche. Top each with one of the remaining cookies, gently pressing down on the dulce du leche so it spreads between the cookies and out to the edges.
Microwave the chocolate chips in a medium microwave-safe bowl in 30-second intervals, stirring between each, until melted and smooth. Let cool for about 5 minutes.
Working with 1 or 2 cookies at a time, gently drop them into the melted chocolate. Use 2 forks to gently turn to coat, then lift them out and let some of the excess chocolate drip back into the bowl; place on the reserved baking sheet. Refrigerate until the chocolate is firm, about 30 minutes. Serve the cookies at room temperature.

Cook’s Note

When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.) Make sure to use the thicker, spreadable dulce de leche found in cans, from brands such as Nestle or J. Hungerford Smith (both of which are available in most supermarkets).

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