chocolate chip cookie stuffed chocolate hamantaschen

chocolate chip cookie stuffed chocolate hamantaschen | withloveandcupcakes.com

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 | withloveandcupcakes.com

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 | withloveandcupcakes.com

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!
ingredients
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
instructions
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.
notes
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 | withloveandcupcakes.com

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Comments

  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!

      • Tara says

        I had the same problem and added an extra quarter cup of flour to stiffen the dough. Worked perfectly! But my question is – how did you get the outer shell to come out so dark? Maybe it was the brand of cocoa?

        • says

          i think you’re right – different brands of cocoa will have slightly different coloring. i didn’t do anything special color-wise – they just sort of came out as you see them here. glad you got to make these!

  6. Sheryl Hausman says

    Adina-
    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.

    • Rachel says

      Andrew, there’s no charge for the benefit of reading this (or other blogs) and there’s no requirement to comment. People posting their recipes are giving them to us as a gift. I find it really impolite to critique someone’s writing or style. If you had trouble with the recipe, or had a question, then that’s one thing. But if people only have not nice things to say then don’t say anything at all!

  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!

  16. says

    Love your writing style , Love the recipe , love the simplicity of both…. The wonders of childhood revisited ;-) … Follow your dreams or relax and enjoy a fascinating hobby….I have fiends who have left 9-5 jobs to beome chefs and fodie bloggers …Most people do not realize that Professional Firefighters are a very large segment of the frustrated chef population … Do You Girl!

  17. Rachel says

    Lisa, did you use natural or Dutch cocoa in the dough? I’m guessing natural since you used baking powder. I only have Dutch so I’m thinking of adding a 1/2 teaspoon of baking soda, what do you think?

  18. Sheila says

    My experience was the same as Pam’s. I followed the recipe exactly and the outer dough looked great until I baked it, when it faded a great deal and was nowhere near as dark as in the pictures (it was dark like the pictures before I baked it). Not surprising given its light color once baked, the outside didn’t taste like chocolate at all, and didn’t hold up to the standard of sugar cookies in our house. It was like wrapping a chocolate-chip cookie in a very, very bland sugar cookie. I’m throwing the whole batch out. The idea is a great one, though! It would probably taste better with butter instead of oil, a lot more cocoa , and a dash of salt, but I haven’t done the experiments to try it.

  19. Rebecca Sherman says

    Made these today with a friend, she had no cocoa, so we used hot cocoa mix and put a little less sugar in the batter. I figured that swap was the reason that the outer shell was so light compared to your picture, but now I’m not so sure. Regardless, they came out TASTY and we had enough cookie dough to make a very small tray of cookie bars. Thanks for the recipe, looking forward to surprising my daughters with a really yummy treat.

  20. Sheryl Cohn says

    Lisa….gave these a try. Pinched up the edges to make “triangle”, even wet a bit to help with the edges sticking, but when they baked most came apart. Was the dough too dry? Any special secrets to keeping Haman’s hat together?? Thanks……Sheryl

    • says

      your dough was probably a little too dry… there’s no real way of knowing why – it could be the moisture level in your kitchen, or maybe it was an issue with measurement. your idea of wetting the edges with a little water should have helped, but another issue could have been that you may have overfilled your hamantaschen – then the filling expanded while baking, pushing the edges out too much. next time, i’d try putting a little less filling in each cookie.

  21. gena says

    So, here I am with cookie dough made & hamantashen dough rolled out but I can’t get it off the wax paper. Too sticky. Major fail. SO disappointed ;( Any way I can still salvage this?

    • says

      oh, no – sorry to hear! i’d try sprinkling the wax paper with plenty of flour before rolling. if the dough is still too wet, you can try putting it back into your mixer and adding flour to it, 1/4 cup at a time, until it reaches a better consistency.

  22. says

    I had a lot of trouble with the dough. It came out way too dry, so I had to add water just to be able to roll it. Maybe next time I’ll use my regular hamentashen dough recipe, add some cocoa and make the filling. Great idea, though!

  23. Sarah B. says

    Made these with my daughter, and they came out great! We made them dairy (using milk and butter). The only other change I made was to add a pinch of salt to the chocolate dough. Great recipe! Great idea! Thank you for sharing it!

  24. says

    Mine turned out great. I was having problems with them sticking, so I dusted the wax paper with a bit of cocoa–more chocolate is never wrong–and I made them a bit thicker. I used Hershey’s Dark cocoa, and I used butter in the chocolate chip dough. I also filled some of the cookies with Nutella.

  25. Lisa says

    I don’t have parchment paper in the house. Can I bake them just on a baking sheet? Should I spray it with cooking spray first?

  26. says

    This was my very first time ever to make Hamentaschen. I wanted to make a less-traditional variety to take for our congregational Purim celebration, and this one looked just perfect.

    This recipe turned out very well, in spite of the fact that I had to improvise on the chocolate dough because I had no milk, dairy or otherwise. I used coffee. The cocoa I had on hand was Hershey’s Special Dark, which I have never used before. I have read online that it tends to be a little drier than some cocoas. I believe it! I had to add almost half a cup of water to the dough just to get it to finish mixing.

    Rolling the dough between wax paper did not work well for me–my dough was way too sticky! I switched to parchment paper, and the dough cutouts peeled right up.

    My husband and I prefer a sweeter cookie. After tasting my first few trial cookies, he suggested that I sprinkle the next tray of cookies with granulated sugar before baking. I decided instead to lay the cutout circles onto a plate of sugar, so that sugar would coat the entire outside. Let me tell you, it made the cookies SO much easier to handle and shape into the triangles. They look kind of sparkly, and are just sweet enough for our taste.

    This is a great recipe. Thanks for posing it!

  27. says

    Hey Lisa,
    I’m a thirty something Israeli filmmaker turned baker (kind of…) and I love your blog.
    Just wanted to say “Kol Ha Kavod” on the good work and the beautiful pictures. I’ve shared your “Oznei Haman” recipe with my friends out here in Israel, so I’m glad to inform you that your sweets have made it to the holy land :)

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