Chocolate-Filled Hamantaschen
This post may contain affiliate links. Read my full disclosure policy. Thes vanilla-scented hamantaschen cookies surround a brownie-like chocolate filling. “Pure ambrosia. Delicious, delicate cookie and the filling is like the food of the gods, especially when warm.” What You’ll Need To Make Chocolate-Filled Hamantaschen All-Purpose Flour: Provides structure for both the cookie dough and the filling. Measure by spooning it into the measuring cup and leveling it off to ensure accuracy. Baking Powder: Helps the dough rise slightly and become light. Butter: Adds richness and tenderness to the dough and melts with the chocolate to create a smooth filling. Sugar: Sweetens the dough and helps achieve a tender texture. Additionally, it helps to sweeten the filling and balance the bitterness of the unsweetened chocolate. Egg: Binds the ingredients together, adds moisture to the cookie dough, and helps to set the filling as it bakes. Egg Yolk: Adds richness to the dough and contributes to a tender texture. Vanilla Extract: Enhances the flavor of both the dough and the filling with its aromatic richness. Unsweetened Chocolate: Provides a deep chocolate flavor. Jump to the printable recipe for precise measurements All-Purpose Flour: Provides structure for both the cookie dough and the filling. Measure by spooning it into the measuring cup and leveling it off to ensure accuracy. Baking Powder: Helps the dough rise slightly and become light. Butter: Adds richness and tenderness to the dough and melts with the chocolate to create a smooth filling. Sugar: Sweetens the dough and helps achieve a tender texture. Additionally, it helps to sweeten the filling and balance the bitterness of the unsweetened chocolate. Egg: Binds the ingredients together, adds moisture to the cookie dough, and helps to set the filling as it bakes. Egg Yolk: Adds richness to the dough and contributes to a tender texture. Vanilla Extract: Enhances the flavor of both the dough and the filling with its aromatic richness. Unsweetened Chocolate: Provides a deep chocolate flavor. Jump to the printable recipe for precise measurements Step-By-Step Instructions Begin by combining the dry ingredients in a bowl. Whisk well. Cream the butter and sugar. Beat in the egg, egg yolk and vanilla. Add the flour. Mix slowly until the dough comes together. Scrape the dough out onto a very lightly floured surface. Divide the dough in half and form into two 6-inch discs. Wrap in plastic and chill for several hours. Meanwhile, make the filling by melting the butter in the microwave. Add the chopped chocolate and stir until melted. Stir in the sugar, vanilla and salt. It will look grainy. Add the egg and mix well. The mixture will look greasy; that’s okay. Add the flour. Mix until shiny and smooth. Remove the dough from the fridge and let sit out at room temperature until supple enough to roll, about 15 minutes. On a very lightly floured work surface, roll about 1/8-inch thick. Use a cookie cutter or glass to cut out 3-inch circles. Re-roll and re-cut the dough as necessary. Place the dough circles on lined baking sheets, then spoon a teaspoon of the chocolate filling in the center of each one. Bring three sides of each cookie partially over the filling and pinch the corners together to form a triangle shape. Freeze the unbaked cookies for 10-15 minutes, or until firm. Then bake for about 12 minutes, until lightly golden. You May Also Like RecipeComments (37)Add Comment Recipe Comments (37) Add Comment Ingredients For the Cookie Dough 2 cups all-purpose flour, spooned into measuring cup and leveled-off with a knife, plus more for rolling the dough (see note) ½ teaspoon baking powder ¼ teaspoon salt 1 stick (¼ pound) unsalted butter, softened 1 cup sugar 1 large egg 1 large egg yolk 1½ teaspoons vanilla extract 2 cups all-purpose flour, spooned into measuring cup and leveled-off with a knife, plus more for rolling the dough (see note) ½ teaspoon baking powder ¼ teaspoon salt 1 stick (¼ pound) unsalted butter, softened 1 cup sugar 1 large egg 1 large egg yolk 1½ teaspoons vanilla extract For the Chocolate Filling 3 tablespoons unsalted butter 2 ounces unsweetened chocolate, finely chopped ¼ cup plus 2 tablespoons sugar ½ teaspoon vanilla extract ⅛ teaspoon salt 1 large egg 1 tablespoon all-purpose flour 3 tablespoons unsalted butter 2 ounces unsweetened chocolate, finely chopped ¼ cup plus 2 tablespoons sugar ½ teaspoon vanilla extract ⅛ teaspoon salt 1 large egg 1 tablespoon all-purpose flour Instructions For the Cookie Dough In medium bowl, whisk together the flour, baking powder and salt. In the bowl of an electric mixer, beat the butter and sugar until light and fluffy, about 3 minutes. Scrape down the sides of the bowl with a rubber spatula, then beat in the egg, egg yolk, and vanilla. On low speed, beat in the flour mixture until just incorporated, scraping down the sides of the bowl as necessary. Scrape the dough onto a very lightly floured surface (just a few pinches of flour) and knead with your hands a few times until smooth. Divide the dough into 2 pieces and form each into a 6-inch disc. Wrap each disc in plastic wrap and refrigerate until firm enough to roll, a few hours or overnight. In medium bowl, whisk together the flour, baking powder and salt. In the bowl of an electric mixer, beat the butter and sugar until light and fluffy, about 3 minutes. Scrape down the sides of the bowl with a rubber spatula, then beat in the egg, egg yolk, and vanilla. On low speed, beat in the flour mixture until just incorporated, scraping down the sides of the bowl as necessary. Scrape the dough onto a very lightly floured surface (just a few pinches of flour) and knead with your hands a few times until smooth. Divide the dough into 2 pieces and form each into a 6-inch disc. Wrap each disc in plastic wrap and refrigerate until firm enough to roll, a few hours or overnight. For the Chocolate Filling Place the butter in a medium microwave-safe bowl. Microwave on high until melted, about one minute. Add the chopped chocolate and stir until the mixture is completely melted and smooth (zap again in the microwave for 20 seconds if necessary). Stir in the sugar, vanilla and salt. The mixture will look grainy -- that's okay. Add the egg and stir until incorporated. Stir in the flour and beat with a spoon until the mixture is smooth, about 30 seconds. Cover and refrigerate until ready to use. Place the butter in a medium microwave-safe bowl. Microwave on high until melted, about one minute. Add the chopped chocolate and stir until the mixture is completely melted and smooth (zap again in the microwave for 20 seconds if necessary). Stir in the sugar, vanilla and salt. The mixture will look grainy -- that's okay. Add the egg and stir until incorporated. Stir in the flour and beat with a spoon until the mixture is smooth, about 30 seconds. Cover and refrigerate until ready to use. To Assemble Preheat oven to 350°F and position racks in upper and lower thirds of the oven. Line two baking sheets with parchment paper. Remove 1 disc of dough from the refrigerator and let sit at room temperature until supple enough to roll, about 15 minutes. Place the dough on a very lightly floured work surface and knead with your hands a few times to soften it up. It will continue to soften as you work with it. Roll to about ⅛-inch thick, turning and dusting with more pinches of flour as necessary. (Take care not to use too much flour, and don't worry if the dough starts to crack at the edges; just cut the cookies from the inside area. When you re-roll the scraps, the dough will be softer and less prone to cracking.) Using a cookie cutter or glass, cut out 3-inch circles and place them about ½-inch apart on the prepared pans. Re-roll and re-cut any excess dough. Scoop and place a level teaspoon of the chocolate filling in the center of each cookie (do not overfill). Bring 3 sides of each cookie up to partially cover the filling, then firmly pinch the edges of the cookie to seal the corners and form a triangle. Place the unbaked hamantaschen in the freezer for 10-15 minutes to firm up (if your pans don't fit in your freezer, you can place them in the fridge for 30 minutes). Bake for 12 minutes, turning the pans halfway through baking, until lightly golden around the edges. Let cool on the pan for a few minutes, then transfer to a rack to cool completely. Repeat with the remaining dough until all of the cookies are baked. Note: It is very important to use the spoon and level method for measuring the flour for this recipe, or your dough will be dry. Use a large spoon to lightly spoon the flour into the measuring cup until it is slightly overflowing, then use the flat side of a knife to level it off so that it's even with the top of the measuring cup. Do not tap the cup, as this causes the flour to settle in and become more dense. Note: The cookies are best on the day they are made but will keep for a few days in an airtight container. Cool the cookies completely before stacking or storing. Freezer-Friendly Instructions: The Dough can be Frozen for up to 3 Months: Shape the dough into 2 discs, wrap each securely in plastic wrap, and place them in a sealable bag. When ready to bake, remove the disks from the freezer, thaw the dough for 1 to 2 days in the fridge, and then proceed with recipe. To Freeze After Baking: Let the hamantaschen cool completely and store in an airtight container separating layers with parchment paper or aluminum foil. Before serving, remove the cookies from the container and let them come to room temperature. Preheat oven to 350°F and position racks in upper and lower thirds of the oven. Line two baking sheets with parchment paper. Remove 1 disc of dough from the refrigerator and let sit at room temperature until supple enough to roll, about 15 minutes. Place the dough on a very lightly floured work surface and knead with your hands a few times to soften it up. It will continue to soften as you work with it. Roll to about ⅛-inch thick, turning and dusting with more pinches of flour as necessary. (Take care not to use too much flour, and don't worry if the dough starts to crack at the edges; just cut the cookies from the inside area. When you re-roll the scraps, the dough will be softer and less prone to cracking.) Using a cookie cutter or glass, cut out 3-inch circles and place them about ½-inch apart on the prepared pans. Re-roll and re-cut any excess dough. Scoop and place a level teaspoon of the chocolate filling in the center of each cookie (do not overfill). Bring 3 sides of each cookie up to partially cover the filling, then firmly pinch the edges of the cookie to seal the corners and form a triangle. Place the unbaked hamantaschen in the freezer for 10-15 minutes to firm up (if your pans don't fit in your freezer, you can place them in the fridge for 30 minutes). Bake for 12 minutes, turning the pans halfway through baking, until lightly golden around the edges. Let cool on the pan for a few minutes, then transfer to a rack to cool completely. Repeat with the remaining dough until all of the cookies are baked. Note: It is very important to use the spoon and level method for measuring the flour for this recipe, or your dough will be dry. Use a large spoon to lightly spoon the flour into the measuring cup until it is slightly overflowing, then use the flat side of a knife to level it off so that it's even with the top of the measuring cup. Do not tap the cup, as this causes the flour to settle in and become more dense. Note: The cookies are best on the day they are made but will keep for a few days in an airtight container. Cool the cookies completely before stacking or storing. Freezer-Friendly Instructions: The Dough can be Frozen for up to 3 Months: Shape the dough into 2 discs, wrap each securely in plastic wrap, and place them in a sealable bag. When ready to bake, remove the disks from the freezer, thaw the dough for 1 to 2 days in the fridge, and then proceed with recipe. To Freeze After Baking: Let the hamantaschen cool completely and store in an airtight container separating layers with parchment paper or aluminum foil. Before serving, remove the cookies from the container and let them come to room temperature. Nutrition Information Powered by Per serving (30 servings) Serving size: 1 cookie Calories: 119 Fat: 6g Saturated fat: 3g Carbohydrates: 16g Sugar: 9g Fiber: 1g Protein: 2g Sodium: 41mg Cholesterol: 24mg Per serving (30 servings) Serving size: 1 cookie Calories: 119 Fat: 6g Saturated fat: 3g Carbohydrates: 16g Sugar: 9g Fiber: 1g Protein: 2g Sodium: 41mg Cholesterol: 24mg This website is written and produced for informational purposes only. I am not a certified nutritionist and the nutritional data on this site has not been evaluated or approved by a nutritionist or the Food and Drug Administration. Nutritional information is offered as a courtesy and should not be construed as a guarantee. The data is calculated through an online nutritional calculator, Edamam.com. Although I do my best to provide accurate nutritional information, these figures should be considered estimates only. Varying factors such as product types or brands purchased, natural fluctuations in fresh produce, and the way ingredients are processed change the effective nutritional information in any given recipe. Furthermore, different online calculators provide different results depending on their own nutrition fact sources and algorithms. To obtain the most accurate nutritional information in a given recipe, you should calculate the nutritional information with the actual ingredients used in your recipe, using your preferred nutrition calculator. See more recipes: Cookies & CandyFreezer-FriendlyHolidaysMake-AheadJewish Cookies & Candy Freezer-Friendly Holidays Make-Ahead Jewish