Recipes Desserts Cookies Chocolate Cookie Recipes Chocolate Hamantaschen 5.0 (1) 1 Review 1 Photo These chocolate hamantaschen cookies are soft and cakey and not overly sweet. The chocolate filling is almost like a fudgy brownie. Just the right amount! Submitted by Pam Lolley Updated on February 22, 2023 Tested by Allrecipes Test Kitchen Tested by Allrecipes Test Kitchen The Allrecipes Test Kitchen staff are a team of culinary pros who make and vet recipes using only equipment you'd find in a home kitchen. Staff credentials vary but include training at the Culinary Institute of America; kitchen stints in fine dining restaurants; and countless hours in the test kitchen itself. Meet the Allrecipes Test Kitchen Save Rate Print Share Close Add Photo Prep Time: 45 mins Cook Time: 45 mins Chill Time: 4 hrs 50 mins Total Time: 6 hrs 20 mins Servings: 42 Yield: 42 cookies Jump to Nutrition Facts Cook Mode (Keep screen awake) Ingredients 1x 2x 4x Oops! Something went wrong. Our team is working on it. Original recipe (1X) yields 42 servings Dough: 1 cup unsalted butter, softened ¾ cup white sugar 2 large eggs 1 tablespoon vanilla extract 3 ½ cups all-purpose flour, plus more for dusting 1 tablespoon baking powder ¼ teaspoon kosher salt ⅓ cup whole milk Filling: 3 tablespoons unsalted butter 2 ounces bittersweet chocolate, finely chopped 6 tablespoons white sugar ½ teaspoon vanilla extract ¼ teaspoon kosher salt 1 large egg 1 tablespoon all-purpose flour Directions Prepare dough: Beat butter and sugar at medium speed with a stand mixer fitted with the paddle attachment until combined and creamy, about 1 minute. Dotdash Meredith Food Studios Add eggs, 1 at a time, and beat until just combined after each addition, stopping to scrape down the sides of the bowl as needed; beat in vanilla just until combined, about 30 seconds. Whisk together flour, baking powder, and salt in a medium bowl. Add flour mixture to butter mixture alternately with milk, beating at low speed, until combined, about 1 minute. Dotdash Meredith Food Studios Divide dough in half and shape each into a disk. Wrap each in plastic wrap and chill for at least 4 hours, or overnight. Dotdash Meredith Food Studios Prepare filling: Place butter and chopped chocolate in a small microwave-safe bowl. Melt in microwave on high (100%) power for 1 to 1 1/2 minutes, stirring every 20 seconds, until melted and smooth. Stir in sugar, vanilla, and salt until fully combined (mixture will look grainy). Stir in egg and flour until completely combined and smooth. Chill for 30 minutes. Dotdash Meredith Food Studios Preheat the oven to 350 degrees F (175 degrees C). Line baking sheets with parchment paper. Remove 1 dough disk from the refrigerator and divide in half; cover and keep 1 dough half in refrigerator. Roll dough out on a floured surface until 1/8 inch thick; using a 3-inch round cutter, cut dough into circles (only re-roll scraps once). Dotdash Meredith Food Studios Place dough rounds on prepared baking sheets, about 1 1/2 inches apart. Dotdash Meredith Food Studios Top each dough round in the center with 1 level teaspoon of the chocolate filling (keep filling in refrigerator when not in use). Fold one edge inwards, slightly covering the filling. Fold the next edge slightly overlapping, and then the last, creating a triangle with overlapping sides so you still can see an almond-sized amount of the filling. Press dough down to ensure dough sticks together. Dotdash Meredith Food Studios Chill in a freezer for 10 minutes or in a refrigerator for 30 minutes. Repeat procedure with remaining dough and filling. Bake in the preheated oven in the middle rack, in batches, until lightly browned around bottom edges and bottoms, 12 to 14 minutes. Dotdash Meredith Food Studios Cool completely on wire racks about 10 minutes. Cook's Notes: The dough gets soft really quickly - keep unused dough refrigerated. Don't re-roll scraps but one time as it makes the cookies very tough. It's important to keep your hands clean and free of filling to keep a clean-looking cookie as an end result. These can be kept chilled until ready to bake, or frozen and placed in heavy-duty zip-top bags and baked when ready. I Made It Print Nutrition Facts (per serving) 120 Calories 6g Fat 15g Carbs 2g Protein Show Full Nutrition Label Hide Full Nutrition Label Nutrition Facts Servings Per Recipe 42 Calories 120 % Daily Value * Total Fat 6g 8% Saturated Fat 4g 19% Cholesterol 27mg 9% Sodium 65mg 3% Total Carbohydrate 15g 5% Dietary Fiber 0g 1% Protein 2g 4% Potassium 26mg 1% * Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs. ** Nutrient information is not available for all ingredients. Amount is based on available nutrient data. (-) Information is not currently available for this nutrient. If you are following a medically restrictive diet, please consult your doctor or registered dietitian before preparing this recipe for personal consumption.