chocolate chip cookie stuffed chocolate hamantaschen

chocolate chip cookie stuffed chocolate hamantaschen |

you may have noticed these triangular stuffed cookies popping up all over pinterest lately. that’s because the jewish holiday of purim is coming up, and these cookies–hamantaschen–are a special purim treat. traditionally, they are made with a basic sugar cookie dough and filled with poppy seed filling or some sort of fruity concoction (my grandmother always made them with prune filling). making hamantaschen before purim is probably one of my strongest childhood memories – every year, a week or two before the holiday, my mom would always make the dough, and then we would get to cut out little circles from it and fill them with various jams, pie fillings, and chocolate chips. now, every year when purim is coming up, i get a little nostalgic for those times.

chocolate chip cookie stuffed chocolate hamantaschen |

lately, a lot of people have started to move away from the traditional hamantaschen recipes in favor of some pretty inspired combinations: lemon poppyseed, pecan pielemon bar, date and almond, and even some savory versions have all been popping up around the blogosphere. so when i started to think about what i’d like to do for hamantaschen this year, i wanted to think of something extra fun and creative. and then it hit me: who doesn’t like cookies stuffed inside other cookies? so i played around with a couple of recipes, and the results were awesome. the chocolate dough is a modified chocolate version of my mother’s recipe, which yields a delicious and slightly crisp but also chewy  sugar cookie, and the chocolate chip cookie dough is a chewy cookie dough from martha, because, well… she knows everything. the final product is crisp on the outside, and chewy on the inside. basically, these are the most fun hamantaschen ever.

chocolate chip cookie stuffed chocolate hamantaschen |

chocolate chip cookie stuffed chocolate hamantaschen
yield: 30-60 hamantaschen, depending on size

chewy chocolate chip cookies inside chocolate sugar cookies: a fun twist on a purim classic!
for the chocolate hamantaschen dough
  • 1 egg
  • 1 egg white
  • ¾ cup sugar
  • ¼ cup plus 2 tablespoons canola oil
  • 3 tablespoons almond milk
  • 2¼ cups all-purpose flour
  • ¼ cup unsweetened cocoa powder
  • 1¾ teaspoons baking powder
for the chocolate chip cookie dough
  • 1 cup plus 2 tablespoons all-purpose flour
  • ¼ teaspoon baking soda
  • ½ cup earth balance, at room temperature
  • ¼ cup sugar
  • ½ cup packed brown sugar
  • ½ teaspoon salt
  • 1 teaspoon vanilla extract
  • 1 egg
  • 1 cup chocolate chips
first, make the chocolate hamantaschen dough
  1. in the bowl of a stand mixer fitted with the paddle attachment, beat the egg, egg white, and sugar on medium speed until combined. add the oil and almond milk and beat until smooth.
  2. in a small bowl, combine the flour, cocoa powder, and baking powder. with the mixer on low speed, gradually add the dry ingredients to the wet ingredients and mix until everything is just combined.
  3. form the dough into a disc and wrap it in plastic wrap. let it chill in the fridge for at least an hour.
meanwhile, make the chocolate chip cookie dough
  1. in a small bowl, combine the flour and baking soda.
  2. again in a stand mixer fitted with the paddle attachment, cream together the earth balance and both sugars on medium speed until the mixture is light and fluffy. add the salt, vanilla, and eggs, and beat until combined. with the mixer on low, slowly add the dry ingredients and mix until everything is combined. stir in the chocolate chips.
then, assemble the hamantaschen
  1. preheat the oven to 350ºf and line a baking sheet with parchment paper.
  2. take about a quarter of the hamantaschen dough and roll it out between two pieces of wax paper to about ¼-inch thickness. use some sort of circular item (a biscuit cutter, a round cookie cutter, a glass) to cut circles out of the dough. top each circle with about a teaspoon of chocolate chip cookie dough.
  3. for each circle, fold up the sides into a triangular shape, and pinch the corners together tightly.
  4. repeat this with the rest of the two doughs, re-rolling the scraps of hamantaschen dough as needed.
  5. bake the hamantaschen on the prepared baking sheet for about 10 minutes, until they are just starting to darken at the corners. the chocolate chip cookie dough should still be a bit soft. let the hamantaschen cool for a few minutes on the baking sheet, then transfer them to a wire rack to cool completely.
i used a 2-inch round biscuit cutter to cut my hamantaschen, and wound up with about 60 of them. they were on the small side, but that's how i like them! but if you like yours on the bigger side, you might want to double the recipe.

chocolate chip cookie stuffed chocolate hamantaschen |

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  1. Elka says

    I was hoping that a doctoral student would know how to write better. My instructors would have docked me. However, the Hamantaschen do look tasty.

    • lisa says

      good thing i’m not planning to submit this post for publication in a scientific journal :) (and since i have published multiple papers in journals already, i’m not too worried about my writing skills). anyway, back to what really matters – i hope you enjoyed this recipe!

  2. Pam says

    I made this this evening with my 12 year old daughter. We prepared it exactly as the recipe instructed. The hamantashen cookie dough was way to dense, bland, and was much lighter in color than the ones pictured. The cookie dough was amazing! Next time we will probably add more sugar and more coco. We were disappointed. We have 40+ hamentashen that no one wants to eat. :(

    • lisa says

      i’m so sorry this recipe didn’t work out for you! if you do try it with different amounts of sugar and/or cocoa, let me know how it turns out. i think the key is to find a dough that is sweet enough for you, but doesn’t overpower the cookie dough, since that is the real star here. i hope you have better results next time!

  3. Clare Yaffe says

    I wish I had seen this earlier…..I just made 200 hamantashen……and that is it till next year!!!

    • lisa says

      earth balance is a buttery spread that is non-dairy and non-hydrogenated. i use it in a lot of recipes because it is free of saturated fat and cholesterol, unlike butter, and it is free of trans fats, unlike margarine. i also use it to make a lot of my recipes non-dairy for kosher purposes. but if you prefer to use real butter, go for it!

    • lisa says

      you can definitely use regular milk. i wouldn’t use sweetened cocoa, because it really has a different flavor and would probably make the dough overly sweet (and it might even change the texture)… but i guess you never know. if you try it, let me know how they turn out!

  4. cookiemonster says

    - Delicious, but only makes about 40 hamentashen :(
    I rolled them out very very thin, and still came out short.
    Next year, I’ll double the recipe.
    (The filling to dough ratio is the perfect right ratio however)

    • lisa says

      i’m glad you liked the recipe! and come to think of it, i guess i did make mine a little on the small side – that explains why i got so many more than you did out of the dough. i’ll note that in the recipe to avoid any confusion. thanks for commenting!

  5. Ariella says

    These came out delicious. I had to substitute oil for the Earth Balance because I’ve never seen such a thing in Israel. The only problem that I had was that the chocolate dough came out way too sticky and soft for folding into cookies even after refrigerating. Adding some more flour did the trick and they came out great! This was a really fun idea, thanks Lisa!