Dulce de leche, a rich and creamy South American caramel made from cooked milk, is the star of these deceptively simple sandwich cookies. Spicing the buttery cookies with cinnamon was a delicious start, and adding anise to the mix took the cookies over the top. The anise enhanced the flavor of the warm cinnamon, and both complemented the milky caramel filling—so much so that we decided to add both spices to the dulce de leche as well. Slow cooking milk for homemade dulce de leche can take a gruelingly long time, so to keep our cookies simple we turned to store-bought and doctored it with a tablespoon of butter for added richness. Melting the butter before adding it to the caramel allowed us to briefly cook the spices in it to bloom their flavor, and the melted butter easily blended into the filling. This made for a fragrant cookie, but we wanted the warm spice flavor to be even more prominent, so we took the cinnamon out of the dough and instead rolled the cookies in cinnamon sugar before baking. Not only did this ensure unmistakable cinnamon flavor in every bite, but the sugary coating—along with the rich amber hue of the filling—made for an attractive presentation.
Ingredients
- 2 cups (10 ounces) all-purpose flour
- 1 teaspoon baking soda
- ½ teaspoon salt
- ½ teaspoon ground anise
- 16 tablespoons unsalted butter, softened
- 1 cup (7 ounces) sugar, plus ½ cup for rolling
- 1 large egg
- 1 teaspoon vanilla extract
- 1 teaspoon ground cinnamon
- 1 tablespoon unsalted butter
- ½ teaspoon ground cinnamon
- ½ teaspoon ground anise
- 1½ cups dulce de leche
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For the Cookies
- Adjust oven rack to middle position and heat oven to 350 degrees. Line baking sheet with parchment paper. Whisk flour, baking soda, salt, and anise together in bowl.
- Using stand mixer fitted with paddle, beat butter and 1 cup sugar on medium-high speed until pale and fluffy, about 3 minutes. Add egg and vanilla and beat until combined. Reduce speed to low and add flour mixture in 3 additions until just combined, scraping down bowl as needed.
- Combine cinnamon and remaining ½ cup sugar in shallow dish. Working with 2 teaspoons dough at a time, roll into 16 balls and space them 2 inches apart on prepared sheet. Bake until edges are firm, 10 to 12 minutes, rotating sheet halfway through baking. Let cookies cool on sheet for 1 minute, place in cinnamon sugar, and turn to coat evenly; transfer cookies to wire rack. Repeat twice more with remaining dough. Let cookies cool completely. For the Filling
- Melt butter in small saucepan over medium heat. Whisk in cinnamon and anise and cook until fragrant, about 1 minute. Off heat, stir in dulce de leche until incorporated. Spread 1½ teaspoons filling over bottom of half of cookies, then top with remaining cookies, pressing lightly to adhere, before serving.
