Chocolate-Filled Hamantaschen

Tested & Perfected Recipes

Thes vanilla-scented hamantaschen cookies surround a brownie-like chocolate filling.

hamantaschen

A golden, vanilla-scented sugar cookie surrounds a brownie-like chocolate filling. These delicious hamantaschen — or hat-shaped Purim cookies — are adapted from Alice Medrich’s wonderful cookie book, Chewy Gooey Crispy Crunchy Melt-In-Your-Mouth Cookies. Of course, kids love them.

What you’ll need to make hamantaschen

ingredients-2

They are simple and easy to make; just be sure to plan ahead as the dough needs to rest for a few hours in the fridge.

How to make hamantaschen

Begin by combining the dry ingredients in a bowl.

dry-ingredients

Whisk well.

whisking-dry-ingredients

Cream the butter and sugar.

creaming-butter-and-sugar

Beat in the egg, egg yolk and vanilla.

beating-egg-and-vanilla

Add the flour.

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Mix slowly until the dough comes together.

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Scrape the dough out onto a very lightly floured surface.

dough

Divide the dough in half and form into two 6-inch discs.

discs-of-dough

Wrap in plastic and chill for several hours. Meanwhile, make the filling by melting the butter in the microwave.

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Add the chopped chocolate and stir until melted.

melted-chocolate

Stir in the sugar, vanilla and salt. It will look grainy.

stirring-in-sugar

Add the egg and mix well.

adding-egg

The mixture will look greasy; that’s okay. Add the flour.

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Mix until shiny and smooth.

glossy-chocolate-filling

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.

cutting-cookies

Place the dough circles on lined baking sheets, then spoon a teaspoon of the chocolate filling in the center of each one.

ready-to-pinch

Bring three sides of each cookie partially over the filling and pinch the corners together to form a triangle shape.

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Freeze the unbaked cookies for 10-15 minutes, or until firm. Then bake for about 12 minutes, until lightly golden.

Chocolate-Filled-Hamantaschen-1

Note: Since a few of you had trouble with the dough being crumbly, I added an extra egg yolk to the cookie dough.

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Chocolate-Filled Hamantaschen

Thes vanilla-scented hamantaschen cookies surround a brownie-like chocolate filling.

Servings: 30 cookies
Prep Time: 45 Minutes
Cook Time: 15 Minutes
Total Time: 1 Hour, plus a few hours for the dough to rest

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)
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 stick (1/4 pound) unsalted butter, softened
  • 1 cup sugar
  • 1 large egg
  • 1 large egg yolk
  • 1-1/2 teaspoons vanilla extract

For the Chocolate Filling

  • 3 tablespoons unsalted butter
  • 2 ounces unsweetened chocolate, finely chopped
  • 1/4 cup plus 2 tablespoons sugar
  • 1/2 teaspoon vanilla extract
  • 1/8 teaspoon salt
  • 1 large egg
  • 1 tablespoon all-purpose flour

Instructions

For the Cookie Dough

  1. In medium bowl, whisk together the flour, baking powder and salt.
  2. 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

  1. 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

  1. Preheat oven to 350°F and position racks in upper and lower thirds of the oven. Line two baking sheets with parchment paper.
  2. 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 1/8-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 1/2-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).
  3. 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.
  4. 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.
  5. 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.
  6. 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 until pliable, 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 Edamam

  • 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.

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Reviews & Comments

  • This chocolate filling was DELISH! I paired it with a little cinnamon—C’mon somebody it was amazing! Great recipe! Love your recipes. As a busy school administrator I use your site often and have never been disappointed. Thank you for your work!

    • — Brandy Gratten on March 23, 2019
    • Reply
  • The filling is amazing. I made these with my 6 year old grandson, and he, and all the others loved them. I used an old family dough recipe, orange juice and oil, very sticky but tasty. I added an extra tablespoon of flour to the filling because it was runny and this may have caused the fillings to puff out a bit. Next yer I will use your dough recipe and of course your chocolate filling. Please consider giving weights in the future.
    Thanks so much for this great recipe.

    • — Elliot on March 19, 2019
    • Reply
    • Hi Elliot, how nice that you made these with your grandson! I’ve added the metric measurements for the next time around. 🙂

      • — Jenn on March 21, 2019
      • Reply
  • The chocolate filling spilled out of it causing them to look like blobs. What did I do wrong?

    • — Rachel on March 15, 2019
    • Reply
    • Hi Rachel, Sorry to hear you’re having a problem with the chocolate leaking out! Did you stick to just 1 level teaspoon of the filling for each cookie? If so, it could be that you didn’t pinch the edges tightly enough (so the chocolate “escaped”) or that you didn’t refrigerate the dough for long enough.

      • — Jenn on March 16, 2019
      • Reply
  • Wonderful and fun to make!

    • — Olga on December 21, 2018
    • Reply
  • Hi Jenn,
    Just found your site while searching for a hamantashen recipe that didn’t use yeast.
    I have tried many before but was not happy with the result.
    3 batches of dough (1 at a time) were made today.
    My favorite way of measuring is by using a scale.
    As a practice, I always read and understand a recipe. That’s how I was trained ( professional chef/Baker retired).
    Followed the instructions as written and paying attention to the flour measuring method that you used. After measuring the 1st cup of flour, I weighed it on my scale in grams and oz. Then doubled the result. The weight for 2 cups of flour resulted to 258g (9.1 oz).
    Sugar was 200g for 1 cup
    Eggs at room temperature.
    Butter is also at room temperature weighing 113 g (1/4 lb).
    I use a large plastic bag (orowheat bread bag from Costco and proceeded to add a 1/8 th of a teaspoon of all purpose flour.
    Shaked the bag to distribute the flour then opened the plastic bag to shake out excess flour. Next I placed the dough in the bag and kneaded it. No extra flour needed during the process. Formed a large circle of dough, open bag cut it in half.
    Form 2 circles one at a time. It’s the only time I handled the dough by hand. I didn’t want it to warm up too much or add a lot of extra flour.
    Each of the 3 separate batches of dough came out the same in texture, suppleness.
    I would say at this stage my hands and eyes tell me it’s going to be a good dough to work with.
    It’s now chilling in the refrigerator until tomorrow to allow it to relax.
    Will let you know the next stage.
    Thanks for posting this recipe. So far it looks and feels great. 😊

    • — Monina on May 30, 2018
    • Reply
    • More notes:
      Dough was allowed to rest in the refrigerator over night. Then frozen for 2 days. Can also be frozen for 3 months filled or not. No need to thaw just bake it frozen and add a few minutes more time.
      About 3-4 minutes.
      Followed the softening procedure. Floured the board. Rolled out the dough (do not roll it too thin or it will break during baking). Use parchment paper baking pan.
      Cut out circles of dough and lay it directly on the baking pan. After the pan is filled,
      place the pan in the freezer for 5 to 7 minutes. This helps the dough relax and firm up a little ( since it’s soft).
      Now beat an egg. Take the dough circles out of the freezer. Let it sit out for a minute. Brush the circle dough using a small brush with the beaten egg. Fill the center with any filling. The egg is your glue.
      If it’s a fruit filling make sure it’s not runny.
      It can be made from dried fruits and simmered in juice. Then puréed.
      Nuts and chocolate is also very good.
      Jenn’s chocolate filling is excellent.
      Form the cookie in the pan. Less handling the better. Use a small offset spatula or knife to lift the sides to form the 3 corners and your fingers..
      The spatula helps keep the circles nice and neat.
      Freeze.
      Before baking I brushed the hamantaschen with egg wash.
      The dough is very good.
      The recipe is very good.
      It will go in my pink binder where my 5 star recipe is filed.
      Thanks Jenn for this wonderful recipe.
      PS:
      None of the 48 hamentaschen opened.
      They are perfectly beautiful.

      • — Monina S Naylor on June 3, 2018
      • Reply
      • Hi Jenn,
        This chocolate filling is excellent when making chocolate Rugelach.
        It doesn’t runout.
        When it hardens, just pop it in the microwave for a few seconds until it spreadable again. 10-15 seconds. Check it and stir.

        • — Monina on July 2, 2018
        • Reply
  • I am a baker, but had a terrible time with the dough. It was too sticky to use. I don’t know what I did wrong.

    • — Renee K on February 24, 2018
    • Reply
    • Hi Renee, Sorry you had a problem with this! I’m wondering if maybe the dough needed a bit more flour – did you make any changes to the recipe?

      • — Jenn on February 24, 2018
      • Reply
  • I used Nutella instead of the chocolate filling. My husband (who is highly critical) called them “perfect”. The cookie tastes like shortbread. Thanks for a wonderful recipe!

  • yummy but didn’t hold their shape.

    • Easily the most delicious Hamantaschen I’ve ever had. Recipe is straightforward and pretty easy to prepare. Unfortunately many did collapse and leak, though they were still just as tasty!

    • Mine too! They totally collapsed and oozed together 🙁 It was so disappointing after all that work :/

      • — Deborah on February 26, 2018
      • Reply
  • These are the best Hamantaschen cookies and will be our go-to recipe from now on. Last year, when I made them for the first time, the dough cracked on me as well, but we figured out that I was scooping the flour into a measuring cup instead of spooning it and then leveling it off. My method added more flour than the recipe called for and made the dough dry. This year, I used the recommended spoon/level method and I didn’t have that problem. The brownie in the middle is awesome and my kids can’t stop eating them! Thanks Jenn!

  • Not a good cookie recipe compared to the one we used at our Temple. Dough cracked very easily, even though I followed the directions exactly and refrigerated the dough overnight. Would crack especially bad when I tried shaping into the hats/pockets. Will not be using this recipe again.

  • i made this yesterday and the chocolate all melted away!! why was it so?

    • So sorry you had trouble, Tresa. Can you explain further what happened to the chocolate? Or send me a photo at [email protected]?

  • The cookies are delicious!!! I just have one problem: several of the cookies’ sides did not hold up after baking. I don’t know what I did wrong.

    Thanks,
    Tran

    • Hi Tran, Do you mean they flattened out? Could you send me a photo?

  • Chocolate cookies came out very yummy. After an initial problem with the dough, I let it sit for 4 hours in fridge and was able to roll out as per directions. Mine weren’t as pretty as pictured but delicious. Filling is to die for.

    thanks Jen!

  • Thank you, Jen! This recipe came just in time yesterday as I was planning to bake hamentaschen for a family gathering. I made three different variations and these were the favorite! The brownie filling was delish!

  • Help!
    I’m trying to make dough and it is very very dry. Not forming a ball. Advise as I double checked measurements and not sure what is going on.

    • Hi Jen, Did you add the egg?

    • I am so glad you said that. We are rolling very dry dough as well. Even made it twice to be sure. Something doesn’t seem right.

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