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While I was coming up with my Apple Cinnamon Spice Hamantaschen recipe, I was thinking about other dough flavors, which lead to a hankering for graham crackers, which lead to thoughts about S’mores, which lead to – why not make a graham cracker hamantaschen dough, fill it with brownies, and top it with a marshmallow!??! … So, um, I did. And you know what? I have no regrets: S’mores Brownie Hamantaschen was thus born on Cinnamon Shtick!

What are Hamantaschen?

They are triangular shaped cookies (or pastry) that are made with a variety of different fillings. Why are they triangular? Long story short, they are traditionally made for the Jewish holiday of Purim — a joyous holiday that commemorates the saving of the Jews from an evil dude named Haman. According to legend, Haman wore a three-cornered hat. (Very fashion-forward for such a hateful man!) Why they decided to shape cookies like his hat is beyond me. All I know is that, made properly, they are delish.

Why S’mores Brownie Hamantaschen?

Um, why not? Hamantaschen come in all sorts of fun flavors. The spirit of them is the shape. The flavor possibilities are unlimited.

How to Make S’mores Brownie Hamantaschen

1. Make the graham cracker hamantaschen dough

I adapted this graham cracker hamantaschen dough from the basic hamantaschen dough in Shannon Sarna’s Modern Jewish Baker. The dough is very simple make. If you cannot find graham cracker crumbs, just buy regular graham crackers. You can turn them into crumbs in your food processor or blender. If you weigh your ingredients, this is really easy because you can weigh out the graham crackers, process or blend them, and then dump them in with the rest of the dry ingredients.

With the dry ingredients whisked together, you cream the butter with the sugar, add the eggs and other liquid ingredients. Marry the dry ingredients into the wet ingredients,. Divide the dough in half and wrap each half of dough in plastic wrap, and flatten them out. Pop them in the refrigerator for at least a couple hours and up to 24 hours.

2. Make the brownie hamantaschen filling

The brownie hamantaschen filling comes together quickly and in one pot. Melt down the marshmallows a bit, then add the butter and chocolate to the pot until everything is melted. Stir in the sugars, then the egg and vanilla. Mix in the flour and salt. Pour the brownie batter into a pastry bag or a ziplock bag and refrigerate. (You can cut the corner off a ziplock bag to use it like a piping bag.) Pop the brownie batter into the refrigerator for at least an hour.

3. Roll out the graham cracker hamantaschen dough

Take one of the dough packages from the refrigerator and roll it out into a circle on top of a lightly floured piece of parchment paper. No need to strive for perfection here. You just want to roll the dough out so it is approximately ¼ of an inch thick. If you roll it too thin, the dough will rip as you remove it from the parchment. Use a round cookie cutter approximately 2½ inches in diameter to cut circles out. Place the circles on parchment lined baking sheets. Gather any dough scraps, form them into a mound, and roll it out again to cut as many circles as you can. Keep repeating until you’ve used all the dough. If the dough becomes too warm and difficult to work with, place it in the refrigerator for 15 minutes.

Once the circles are cut, place them on the prepared baking sheets into the refrigerator. Repeat with the remaining half of dough in the refrigerator.

If you would like a little guidance on the process of rolling and cutting the hamantaschen dough, take a look at my Apple Cinnamon Spice Hamantaschen post.

4. Fill the graham cracker hamantaschen dough with the brownie filling

Pipe approximately 1 teaspoon of the brownie filling into the center of each circle. Do not over fill them! Lightly flour your fingertips and form each circle into triangles by folding up the rounds and pinching them tightly in three corners. (If they are not sticking together, wet your fingertip and rub it on the inside where you are trying to create the point.) You want to make sure that the seams are fully closed so that the filling does not break through the barriers while baking. Place the shaped hamantaschen on the prepared cookie sheets.

Hamantaschen dough cut in circles with brownie batter in piping bag
Pour the brownie batter into a piping bag, closing off the ends with chip clips before putting it into the refrigerator for about 1 hour.
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5. FREEZE the s’mores hamantaschen and then bake

This is such a critical step for success! The hamantaschen will not keep their shape if they enter the oven at room temperature. Pop them in the freezer for 15 minutes. Place a miniature marshmallow in the center of each, and bake. The marshmallow will turn a nice golden brown by the time the hamantaschen are done baking.

S’mores Brownie Hamantaschen ready to go in oven
Before baking, place 1 to 3 miniature marshmallows on the brownie filling. While you can certainly put more on, it may get messy as they melt in the oven.
close up of a few s'mores brownie hamantaschen
Look how beautiful and fun these turn out!

Looking for other hamantaschen flavors? Check out:

a S’mores Brownie Hamantaschen illustrated to be roasting a marshmallow
Even alien hamantaschen enjoy s’mores!

Frequently Asked Questions About Making S'mores Hamantaschen

Can s’mores hamantaschen be made dairy free?

Yes. Substitute vegan butter and non-dairy milk  in the recipe.

Do I have to freeze the s’mores hamantaschen before baking?

Yes. The hamantaschen will not hold their shape if you do not freeze them before baking.

Can I make the s’mores hamantaschen components in advance?

Yes. You can make both the dough and the brownie batter filing up to 24 hours in advance, storing both in the refrigerator.

S’mores Brownie Hamantaschen

5 from 26 votes
Prep Time 30 minutes
Cook Time 9 minutes
Refrigeration time 2 hours 15 minutes
Total Time 2 hours 54 minutes
Servings 40 cookies
Calories 106
Graham cracker cookies filled with fudgy brownies and topped with marshmallows, these are not your Bubbe's hamantaschen!

Ingredients

Graham Cracker Hamantaschen Dough:

  • 165 grams all purpose flour (1¼ cups plus 1 Tablespoon)
  • 170 grams graham cracker crumbs (2 cups)
  • ¼ teaspoon baking powder
  • ¼ teaspoon salt
  • 113 grams unsalted butter at room temperature (8 Tablespoons. or ½ cup)
  • 150 grams sugar (¾ cup)
  • 1 egg at room temperature
  • 1 egg yolk at room temperature
  • 15 grams whole milk (1 Tablespoon)
  • 1 teaspoon vanilla

Brownie Filling:

  • 30 grams miniature marshmallows (½ cup)
  • 57 grams unsalted butter (4 Tablespoons)
  • 57 grams unsweetened chocolate (2 ounces)
  • 50 grams sugar (¼ cup)
  • 55 grams light brown sugar (¼ cup)
  • 1 egg (beaten)
  • ½ teaspoon vanilla
  • 30 grams all purpose flour (2 Tablespoons)
  • teaspoon salt
  • Miniature marshmallows for the tops

Instructions 

  • Hamantaschen Dough. In a bowl, whisk together the flour, graham cracker crumbs (see Notes below), baking powder, and salt. Put aside.
  • In a mixer, cream the butter and sugar together for 2-3 minutes. Add the egg, the egg yolk, milk, and vanilla and beat until all the liquid ingredients are fully incorporated, approximately 2 minutes.
  • With the mixer off, pour the dry ingredients into the mixer bowl over the liquid ingredients. Turn the mixer on the lowest speed and mix just until the dry ingredients are fully incorporated. (Alternatively, you can mix the dry ingredients in by hand using a rubber spatula.) Do not overmix.
  • Place half the dough on top of a large piece of plastic wrap. Using the plastic wrap, shape the dough into a disk, pushing down on it to thin it out. Fully cover the disk of dough in the plastic wrap and place in the refrigerator for at least two hours and for as long as 24 hours. Repeat with the remaining portion of the dough.
  • Line 2 or 3 cookie sheets with parchment paper.
  • Brownie Filling. Place the marshmallows in a 2 quart saucepan over low heat. As they start to melt, stir them and add the butter and chocolate. Stir occasionally until all ingredients are fully melted. Remove from heat. Stir in the sugar and brown sugar. Set aside for a couple of minutes to make sure the mixture cools completely. Add the beaten egg and vanilla. Mix in the flour and salt just until all the flour is fully absorbed. Place batter into a piping bag or wrap in plastic wrap. Refrigerate the brownie batter for at least one hour.
  • Return to Hamantaschen Dough. Take one of the dough disks from the refrigerator and roll out in between two pieces of parchment paper. Roll the dough so that is approximately ¼ of an inch thick. If you roll it too thin, the dough will rip as you remove it from the parchment. Using a round cookie cutter (I use a 2½ inch diameter), cut as many rounds out as you can. You may need to dip your cutter into some flour to avoid it sticking to the dough. Use a metal spatula dipped in flour to release the rounds. Gather the scraps and roll that clump of dough out and cut more rounds. Keep repeating until you have used all the dough. If at any point the dough becomes too sticky or difficult to work with, cover it in plastic wrap and let it cool in the refrigerator for about 15 minutes.
  • Fill each round with approximately 1 teaspoon of the brownie filling. (It is easiest to fill the cookies by using a piping bag. If you do not have a piping bag.) Do not over fill them! Lightly flour your fingertips and form each circle into triangles by folding up the rounds and pinching them tightly in three corners. (If they are not sticking together, wet your fingertip and rub it on the inside where you are trying to create the point.) You want to make sure that the seams are fully closed so that the filling does not break through the barriers while baking. Place the shaped hamantaschen on the prepared cookie sheets.
  • Place the cookie sheets with the shaped hamantaschen in the freezer for 15 minutes. DO NOT SKIP THIS STEP.
  • Preheat oven to 400° F.
  • Repeat steps 7 through 9 with the remaining disk of dough.
  • Place one to three miniature marshmallows in the center of the brownie mixture. Bake the frozen hamantaschen for 9-10 minutes until they are lightly brown around the bottom edges.
  • Cool completely on pan or a wire rack before serving.

Notes

  • For a parve (non-dairy) version, substitute vegan butter and non-dairy milk.
  • For graham cracker crumbs, place graham crackers (depending on the brand, approximately 9-11 sleeves) into a blender or food processor. Blend or pulse until all crackers are broken down into crumbs.
  • You can make the dough the day before and store it in the refrigerator. Make the brownie mixture within an hour or two of when you intend to fill the hamantaschen.
  • You can also roll and shape the hamanteschen and freeze them for up to 3 months. This way you can bake as many as you want right from the freezer. Place the miniature marshmallows on just before baking.
  • Once baked, store at room temperature in a sealed container. They will remain fresh for at least several days.
  • These also freeze beautifully once baked. Defrost at room temperature for 10-15 minutes.
  • When making the brownie batter, it will make your life tons easier to place it into a piping bag. I used clips made for closing bags of chips on the bottom of the piping bag to leave a little space of air where I will cut it just before piping. I used another chip clip on top to keep the pastry bag closed while it rests in the refrigerator. When it is time to fill the hamantaschen, remove the clip from the top of the bag and twist the top of the bag just above to top of the batter, then remove the bottom clip and cut the tip of the bag off. (If the batter is too thick when you remove it from the refrigerator, massage the bag in your hands for a bit before cutting the tip off the bag off. The heat from your hands will get it to a warmer consistency for piping.)
Calories: 106kcal
Course: Dessert
Cuisine: Jewish
Keyword: cookies, Purim

Nutrition

Calories: 106kcal | Carbohydrates: 14g | Protein: 1g | Fat: 5g | Saturated Fat: 3g | Trans Fat: 1g | Cholesterol: 22mg | Sodium: 55mg | Potassium: 32mg | Fiber: 1g | Sugar: 8g | Vitamin A: 125IU | Calcium: 12mg | Iron: 1mg

7 Comments

  1. These were too hard to resist. Made a batch for a group gathering and they disappeared so quickly.

  2. 5 stars
    love the fillings inside, they turn out so good. Thanks for your recipe, we will be making this again.

  3. 5 stars
    What a fun version of a classic hamantaschen cookie! I don’t have unsweetened chocolate. Will semi-sweet chocolate chips work?

    • Rob Finkelstein Reply

      Sure! You might want to decrease the sugar by about 1-2 teaspoons to compensate for the sugar in the chocolate.

        • Rob Finkelstein Reply

          This recipe was written for unsweetened chocolate. You could use bittersweet or even semi-sweet, but I would reduce the sugar a bit if using either. I would not use chocolate chips, but rather good quality chocolate. I have never used cocoa powder instead of chocolate. If anything, I have added a little cocoa powder to enhance the chocolate. You would have to google to see how to substitute cocoa powder for baking chocolate and give it a try. Let me know how it goes!

  4. 5 stars
    What a fun and wonderful dessert. My family loved these and can’t wait til I make them again. Thanks

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