Chocolate Hamantaschen

Hamantaschen are a fairly ubiquitous offering in the many bakeries and delis in New York, and my first experience was with a raspberry jam-filled pastry the size of my hand on the Upper West Side. More traditional fillings might include sweetened ground poppy seeds, cream cheese, fruit compotes or dried fruit and nut mixtures, but there's almost never anything wrong with chocolate. The doughs one might use for hamantaschen are equally as various, from a tender shortcrust pastry, to a yeast or biscuit dough. What is always consistent, however, is the unique conical shape, always parted just enough to reveal a bit of what's inside.

This recipe, from Alice Medrich's Chocolate Holidays produces something more like a cookie than a pastry, golden bite-sized delights. It's a good idea to make the dough the night before and give it a chance to come together in the refrigerator for several hours. The same thing can be done with the filling.

One tip that I learned only after making these, be sure to really pinch the sides together so the cookie will hold its shape and not split open. Pinching helps to keep the almost flourless filling in place, as well. And speaking of the filling, I had far more of it than cookie rounds on which to spread it. So if you're in need of about half a chocolate filling recipe, you'll be in luck with these leftovers.

Chocolate Hamantaschen


1 stick butter
4 ounces unsweetened chocolate, coarsely chopped
3/4 cup sugar
1 teaspoon vanilla extract
1/4 teaspoon salt
2 cold eggs
2 tablespoons all-purpose flour

Melt the butter and chocolate together in a double boiler, stirring frequently. Remove the top of the double boiler and add the sugar, vanilla extract and salt and continue stirring. Add the eggs one at a time, stirring to incorporate each completely before adding the next. Finally, stir in the flour and beat with a wooden spoon by hand for about a minute. The filling will turn glossy and begin to come away from the bowl. Transfer to a small bowl, cover, and refrigerate until needed.

Cookie Dough

2 cups flour
1/2 teaspoon baking powder
1/4 teaspoon salt
1 stick butter, softened but not squishy
1 cup sugar
1 egg
1 1/2 teaspoons vanilla extract

Mix the first three ingredients with a whisk and set aside. In a large bowl using an electric mixer, cream together the butter and sugar for about 3 - 4 minutes, until light and fluffy. Beat in the egg and the vanilla, and then, on low speed, beat in the flour until just incorporated. Form the dough into two bricks, warp with plastic wrap and refrigerate over night.

Oven preheated to 350, remove the dough from the refrigerator and allow to warm until it becomes supple enough to roll out. Roll each brick individually to a thickness of about 1/8". It is easiest to do this between two sheets of wax paper. You may want to turn the dough over a couple of times, keeping it between the two sheets, to ensure that no deep creases form.

Cut cookies out using a 3" round cutter and transfer cookie rounds to a cookie sheet lined with parchment paper. Put a leveled teaspoon of filling in the center of each cookie round, then bring 3 sides of each round up to partially cover the filling. Pinch the sides together. Cookies should be spaced about 1/2" apart on the sheet.

Bake for a total of 22-24 minutes, rotating the pans half-way through baking. Allow to cool completely on racks.

UPDATE: evidently one reader found 1/8" to be too thin to hold in the filling. It worked fine for me, but this reader, before accusing me of disgracing the hamantaschen world (!!) suggests that you tend toward 1/2" to be on the safe side. I say, use your best judgment when rolling the dough out. If the sides seem too thin to hold the filling in, make them thicker.

* * *

Since these cookies make a perfect treat for the holidays, I'm sending this in to Susan of Food Blogga for Eat Christmas Cookies: Season Two. She's posting the recipes as she receives them, so if you need more ideas for your holiday cookie tray, you can find the round-up here.


Esi said…
I really love hamantaschen. My mom used to buy them for breakfasts when I was growing up, but I only ever had fruit filled versions. The chocolate sound nice and decadent for this time of year.
These are so beautiful, Andrea. They weren't ubiquitous where I grew up, so they seems "fancy" to me. :) Thanks for the lovely entry. Cheers!
Olga said…
These look so good! I tried making hamantaschen last year, but the dough recipe was horrible: it completely melted in the oven.

I'm stumble-int this to make later :)
Anonymous said…
These look really good! I was hoping instead of sending them into Susan's blog you would be sending them to me :)
denver native said…
I can almost taste them! Would you call the cup - art deco?
Anonymous said…
I hope you don't mind me adding this recipe for Christmas. :-)
Dana Treat said…
Love the new look! I have never even seen those let alone eat them. You did a great job.
Anonymous said…
These are always so impressive-looking in display cases with all the colors. Thanks for the recipe! Can't go wrong with Alice Medrich.
Andrea said…
Esi, hamantaschen for breakfast sounds excellent. I gave these to one of my professors and he was delighted when they were filled with chocolate instead of prune (which was his initial thought).

Susan, thanks so much! I can't believe you're undertaking all the x-mas cookies again, but I'm glad you are!

Olga, this dough recipe was quite easy to work with. And yummy!

Chrissy, you should be so lucky!

Denver Native, actually the cup is from the Macintosh house in Glasgow. It's one of my favorite Art Nouveau structures!

Health Funds, please do and let me know how they turn out!

Dana, thanks so much! I'm really happy with the new design as well.

Jude, definitely, although given my baking skills I'm sure I could. But I managed to keep it together this time!
Anonymous said…
These are lovely :-)!!!!
Dazy said…
This would be my son's version of Heaven! I think I'd enjoy it, too!
Anonymous said…
Hi, I just found this recipe and want to make the hamantaschen. Can you tell me how many the recipe makes please? Thank you so much. I can't wait to make these.
Andrea said…
Hi Carol,

The book says 3 dozen, but as I said in my write-up I found myself with extra filling and not enough batter, so you might end up with slightly fewer than the full 3 dozen cookies. But that's the figure I'd work off of.
Anonymous said…

I usually buy hamantashen for Purim, however, this year I decided to bake them myself. Your recipe failed me epically. After being in the oven for about 8 minutes, the edges started to fall and the chocolate started spilling out. I had left over chocolate so I decided to try them again, this time making the dough 1/2 thick and a lot bigger. I made about 6 hamantashen this way, and the edges did not fall, and the chocolate did not spill out. I recommend you change the dimensions of the hamantashen dough to 1/2 inch for future customers and reference. You disgraced the hamantaschen world.
Andrea said…
Okay anonymous, thanks for the heads up. I've updated the post to reflect your experience. However, 'customer' implies that someone pays for a service, which in the case of this blog, no one does. Just saying.
Jean said…
I just finished making these today! They were very good! I made some with apricot jelly for a filling, and some with the chocolate filling. Both turned out beautifully! I also decreased the baking time to about 14 minutes total, so as to keep the edges somewhat soft. My only question would be how to keep them nice and puffy, and not as flat like they turned out for me. I think some spreading can be attributed to the jelly though. Should I put more filling in next time?

To the person claiming she was wronged by this recipe- Perhaps you didn't pinch the corners well enough? This turned out very well for me,
Unknown said…
If you freeze cookies before baking, they won't spread as much.

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