Chocolate-Chili Hamantaschen With Dulce de Leche Filling

By Tami Ganeles-Weiser February 27, 2015

Sweet, creamy dulce de leche — a rich Latino caramel — is a wonderful counterpoint to chocolate’s slightly bitter edge. The warmth of ground chilies hits the palate last. This is a great cookie for adventurous eaters. Photograph by Tami Ganeles-Weiser/The Weiser Kitchen.

Makes 36 cookies

For the dough:
3½ cups unbleached, all-purpose flour, plus more for dusting
½ cup unsweetened cocoa powder
2 tablespoons baking powder
½ teaspoon kosher salt
2 teaspoons ground cinnamon, Mexican preferred
½ teaspoon ground guajillo chili powder (or other medium-hot chili)
½ teaspoon ground ancho chili powder (or other relatively mild chili)
¼ teaspoon ground cayenne pepper, optional
2 sticks (1 cup) unsalted butter, room temperature
1¾ cups light brown sugar
3 large eggs
4 ounces dark chocolate (between 68% and 72% cacao), melted in microwave or a double boiler and cooled to room temperature
3 tablespoons Kahlua or other chocolate liqueur
1 tablespoon pure vanilla extract

For the egg wash:
1 egg white
2 teaspoons water

For the filling:
1 cup dulce de leche

For the drizzle:
8 ounces semisweet chocolate, finely chopped (between 58% and 64% cacao)

1) Make the dough: Combine the flour, cocoa powder, baking powder, salt, cinnamon, guajillo and ancho chili powders and cayenne pepper in a mixing bowl, and whisk well to combine. Set aside.

2) In the bowl of a stand mixer fitted with a paddle attachment (or, if you are using a handheld mixer, in a large mixing bowl), combine the butter and light brown sugar, and mix at medium speed for about 2 minutes, until light and fluffy. Scrape down the sides of the bowl with a rubber spatula. Add the eggs, one at a time, and mix after each addition until incorporated. Add the melted dark chocolate, and mix to combine. With the mixer running at low speed, gradually add the flour mixture and mix to form a dough.

3) Shape the dough into 2 flat, round disks, wrap tightly in plastic, and refrigerate for at least 3 hours, until very firm. (This dough can be refrigerated for up to 5 days before rolling and baking.)

4) Preheat the oven to 350° F. Line 2 rimmed baking sheets with parchment paper or nonstick baking mats and set aside. Lightly flour a work surface and a rolling pin.

5) Place 1 disk of dough on the work surface, and roll out until it is between ¼- and ⅛-inch thick. (The second disk should remain refrigerated while you do the first batch.) With a 3-inch cutter, cut out as many rounds as possible and set on the prepared baking sheet, arranging them about 1 inch apart, 12 circles per sheet. Collect scraps, reroll and cut into additional rounds once.

6) Make the egg wash by whisking the egg white and 1 teaspoon of water in a bowl. With a pastry brush, brush the edges of each round of dough with the egg wash.

7) Place 1 heaping teaspoon of dulce de leche in the center of each. Fold up the edges to shape each filled round into a triangle, pinching them to form points, and leaving a small amount of filling exposed at the top. Repeat with the remaining chilled dough and filling. Brush the dough with egg wash.

8) Chill the filled hamantaschen in the refrigerator for 10–15 minutes.

9) Bake for 9–10 minutes, alternating the baking sheets between the oven racks and turning the trays halfway through the baking time. Let cool for 10–12 minutes. Bake the remaining hamantaschen.

10) Meanwhile, melt the semisweet chocolate in the microwave for 2–3 minutes, stirring often. When it is melted, drizzle decoratively over the hamantaschen.

Tami Ganeles-Weiser is a food anthropologist, trained chef, recipe developer, writer and founder of TheWeiserKitchen.

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