Chocolate-Filled Hamantaschen

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

Chocolate-filled hamantaschen on a lined baking sheet.

Picture a buttery sugar cookie. Now add to that a fudgy brownie. Adapted from Alice Medrich’s wonderful cookie book, Chewy Gooey Crispy Crunchy Melt-In-Your-Mouth Cookies, these delicious chocolate-filled hamantaschen kind of bring those two goodies together in a hat-shaped Purim cookie. Of course, kids love them.

“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

Hamantaschen ingredients including egg, baking powder, and butter.
  • 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 in a bowl of unmixed dry ingredients.

Whisk well.

Whisk in a bowl of dry ingredients.

Cream the butter and sugar.

Stand mixer creaming butter and sugar.

Beat in the egg, egg yolk and vanilla.

Egg and vanilla added to a stand mixer with a butter and sugar mixture.

Add the flour.

Flour added to a stand mixer with a butter mixture.

Mix slowly until the dough comes together.

Dough in a stand mixer.

Scrape the dough out onto a very lightly floured surface.

Ball of dough on a countertop.

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

Two discs of dough.

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

Bowl of melted butter with chocolate.

Add the chopped chocolate and stir until melted.

Spoon in a bowl of melted chocolate.

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

Spoon stirring sugar into a bowl of chocolate.

Add the egg and mix well.

Egg in a bowl of chocolate.

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

Flour in a bowl of melted chocolate with egg.

Mix until shiny and smooth.

Bowl of 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.

Wine glass cutting circles from rolled dough.

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

Circles of dough topped with dollops of chocolate.

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

Person pinching dough into a triangle around chocolate.

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

Chocolate-filled hamantaschen on a lined baking sheet.

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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 to chill the dough


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

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


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 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).
  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 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

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  • 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, 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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  • Pure ambrosia. Delicious, delicate cookie and the filling is like the food of the gods, especially when warm. Warning to all chefs: I used up all my brownie filling greedily for the first disc of dough. You might want to double the brownie recipe! It won’t go to waste regardless of what you do with it.

    • — Lauren on March 5, 2023
    • Reply
  • This is how I did it and what the results were – half the recipe was made after the dough was in the fridge for a few hours and it was a bit messy to work with but the filling was delicious. I had better luck with the second half which I refrigerated for three days, rolled to a 1/4 inch thickness, cut to 3inches round and then used the rolling pin to make the circles bigger to about 4 1/2 to 5 inches. This allowed me to put a heaping teaspoon of the filling in the cookie dough and after folding into a triangle I pushed one ghiradelli’s semi-sweet chocolate chip in the center of the filling. Cause, after all, the filling is the star of this cookie. The dough was much easier to work with and the cookies came out looking like Jenn’s picture.

  • I was wondering how far in advance I can make the filling. Thanks

    • Hi Samantha, I think a day or two in advance should work. Hope you enjoy!

  • I am very disappointed. I made a double batch of this recipe based on all the great reviews and the dough is unmanageable. It is not what I would call “dry” but it cracks and does not hold together AT ALL when I try to fold the hamentashen into triangles. I have to forgo the entire batch and just use it for straight sugar cookies or something else, that is how unworkable it is. I bake a lot and have never had this happen! What did I do wrong?

    • Hi Cindy, I’m sorry you had such a problem with the dough! If it was not holding together, it sounds like it was too dry. Did you make any adjustments to the recipe? did you add both the egg and the egg white? Last, Did you use the spoon and level method to measure the flour? Even a few extra ounces can make a big difference.

  • Excellent filling. Tastes like fudge brownie. I used chocolate chips in the past. This is more homogeneous. The chips didn’t flow and melt. I would use it again.

    • — Karen Fenichel
    • Reply
  • They tasted amazing BUT even with the extra yolk, the dough was so crumbly it was almost impossible to handle. I managed in the end, but some of the hamantaschen opened during baking and some did not look great. Otherwise, delicious!

  • Made these yesterday. As a couple of reviewers mentioned, they didn’t hold their shape. That said, they were delicious, and I will use that chocolate filling over and over! I did use some apricot jam in some of them using the same dough, and they were really delicious as well!

  • 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
    • 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.

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

  • The chocolate filling spilled out of it causing them to look like blobs. What did I do wrong?

    • 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.

  • Wonderful and fun to make!

  • 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. 😊

    • 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.
      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.
      None of the 48 hamentaschen opened.
      They are perfectly beautiful.

      • — Monina S Naylor
      • 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.

  • 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.

    • 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?

  • 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 :/

  • 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?

  • 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.


    • 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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