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 (or butter), 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 egg, 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!

      • Marjorie Strom says

        I wanted to ask the same question. The answer was obvious by the place in the recipe, but please – if it is not essential to how the recipe turns out, always use generic names and do not be overspecific! “Butter or shortning” tells us all we need to know. Same goes for almond milk — incredibly expensive. If you don’t have a reason that it has to be non-dairy, there’s no reason not to use good old-fashioned milk.

        • says

          thanks for the feedback, marjorie! i use non-dairy ingredients for kosher purposes, so there’s definitely a reason for it for me and many readers. plus, a lot of blog readers like to see allergen-free recipes. and, i believe it’s dishonest to readers to write up a recipe that’s different from the one i actually made – so if i made a recipe non-dairy, i’ll write it up as non-dairy. but, people are always welcome to adjust recipes to their own financial and/or dietary needs, and i’m always here to give tips on how to do that if people have questions. enjoy!

    • 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!

  6. Sheryl Hausman says

    Thank you so much for this! I am famous for my hamantashen and I already use a chocolate dough recipe. I make chocolate mint with chopped up york peppermint patties in the middle and they are always a hit! My son has a nut allergy but I would also try heath bar in the middle. I always make a new filling every year (I make about 200 hamantashen a year) for all of our friends and family and this is definitely it for this year!

  7. Aliza says

    Just made these, and they’re delicious! I would probably add a little more sugar or vanilla to the chocolate hamentash dough to make it a drop sweeter, but I love how different they are and how the cookie dough stays soft and chewy… Thanks for enhancing our Purim! :)

  8. Cyndi says

    I am loving the thread and all the comments! Have been home sick for a few days but reading your responses really brings a smile to my face, thanks tizku limitzvot!

  9. says

    Probably a dumb question, but what is Earth Balance? I want to make these instead of our traditional Hamantashen this year, but I don’t know what that is!

    • 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!

  10. Erica says

    I love the idea for the recipe. I agree about the above though, I tried the recipe and I found the flavor a bit lacking. I swirled it with a traditional humantashen recipe and it was a really nice balance to add a bit extra sweetness and aesthetically looked great too (marble style). It did not overpower the cookie dough but complemented it quite well.

    • says

      that sounds great – thanks for sharing! it’s really a personal preference thing – i like the outer dough to be a bit milder to let the cookie dough really shine, but your way sounds amazing too!

  11. says

    Wow wow so creative I’m an obsessed baker foodie crazy girl gonna try this … Was nice to see s/o substitute the milk for me and kosherize it:)!

  12. Emmy says

    Hi Lisa!

    I made these yummy hamentashen and everyone at home is enjoying them, so thank you!
    I have so much left over filling though, any tips of what I can add to it to turn it into regular cookies?

    • says

      i’m so glad you are enjoying them! the filling will actually bake into perfect cookies as-is – just drop mounds of it onto a cookie sheet and bake at 350 for 8-10 minutes.

  13. gena says

    My kids posted this recipe to their FB page, citing it as looking very yummy. I agree. They both live out of state & I thought I’d surprise them with this for their Shaloch Manos. If I make the dough today, will it stay well in the fridge until Sunday when I plan to bake?

  14. Andrew says

    Funny – my reaction to this article was similar to the others. Maybe a good recipe, but this “scholar” has the writing skills of a third grader. Wow. Just wow.

  15. Cyndi says

    With all due respect, we received a gift, in the form of an eclectic twist on the ever-so-expected hamantaschen recipe and we chose to focus, instead, on the writing skills of the benefactor? We need more love, more cookies, more unity and less of these remarks which serve no one. Peace, Love, Shabbat Shalom!