10 Days of Hamantashen, Day 1: Oreo Hamantashen

This is momentous. I’ve been planning 10 Days of Hamantashen for a couple of years, and I’m over the moon at finally finishing to write up that many dough and filling variations! If I have to pick a single Jewish cookie as my favorite, I would probably have to choose hamantashen. Thanks to Uri Scheft’s magical and infinitely adaptable almond shortbread recipe, I’ve been able to create so many flavors, so every year it’s been fun to try something new. I’ve never been a fan of the traditional poppyseed filling, and I find basic jams usually boring, so I’m excited to share some creative and quirky versions that I hope you will enjoy. There will be chocolaty, non-chocolaty, sweet & salty, savory, you name it. The other discovery that revolutionized my hamantashen was Molly Yeh’s knishentashen. That’s right, I’m talking about a marriage of hamantashen and knishes, two iconic Jewish foods that are perfect in and of themselves, but unexpectedly even more than the sum of their parts. Molly is utterly brilliant, and these have now become a staple of my hamantashen repertoire with my own filling flavors.

I honestly want to eat hamantashen all year long, but I end up only making them once per year, and I think that’s what keeps them feeling special every time. (P.S. For the past couple of years I haven’t managed to post a recipe before the actual holiday, so yay for that too!) I’ll be posting a new recipe every day between now and Purim, and I could not be more excited to share these with you– hamantashen have become such a source of joy every March, and I hope you enjoy making them too. If you want to take a peek at any of my past ones, they are linked here:

This recipe pays homage to one of my favorite baking ingredients: black cocoa powder. There are also crushed Oreo cookies in the dough, but the majority of the Oreo flavor comes from the black cocoa, especially in the brownie filling. The dough tasted fairly lightly of cocoa, so I bumped up the cocoa powder from 1 to 2 tablespoons, reducing the flour accordingly (the dough will be a touch darker than pictured here).

Next up for “10 Days of Hamantashen” is Cinnamon Dulce de Leche!

Oreo Hamantashen
Yields 30-40 cookies

This recipe doubles very well if you want to avoid splitting beaten eggs and/or have lots of dough for multiple fillings. I strongly recommend using weight rather than volume to measure ingredients.

For the almond shortbread (adapted from Breaking Breads by Uri Scheft):

  • 360 grams (3 cups) all-purpose flour
  • 50 (½ cup) grams blanched almond flour
  • ¼ cup (35g) Oreo crumbs (from crushed cookies, including the cream centers)
  • 2 tablespoons black cocoa powder
  • 1 teaspoon fine salt
  • 225 grams (2 sticks/1 cup/8 ounces) cold unsalted butter
  • 100 grams (scant 1 cup) confectioners’ sugar
  • ¼ cup (50 grams) granulated sugar
  • 1½ large eggs, beaten, at room temperature
  • 1 teaspoon pure vanilla extract

For the Oreo filling:

  • 1 cup (200g) granulated sugar
  • ¾ cup (60g) black cocoa powder
  • ¼ teaspoon kosher salt
  • 7 tablespoons (100g) unsalted butter, melted
  • 1 large egg
  • 1 egg yolk
  • 1 teaspoon pure vanilla extract
  • ¾ cup (90g) all-purpose flour

To make the almond shortbread dough:
Line a rimmed quarter- or half-sheet pan with a piece of parchment paper and set aside.

Whisk together the all-purpose flour, almond flour, Oreo crumbs, black cocoa powder, and salt in a bowl and keep it nearby.

Lay a piece of parchment paper on your work surface and place 1 stick of butter on top. Smash the butter with a rolling pin several times to soften it, then transfer it to the bowl of a stand mixer fitted with the paddle attachment. Repeat with the remaining stick of butter.

Add the confectioners’ sugar and granulated sugar to the bowl. Mix on low just until the loose sugar is incorporated. Scrape down the bowl and the beater, and mix again for about 30 seconds on medium-low speed. You want the butter to still be cold, and you’re mixing minimally here to avoid aerating the butter.

Pour in the beaten eggs and paddle on low speed until the mixture looks like wet scrambled eggs– the butter chunks should all be coated in egg liberally.

Add the dry ingredients to the bowl (gradually if making a double batch) and mix on low speed until the flour has just been incorporated; it’s helpful to stop and scrape down the bowl and beater midway through.

Turn the dough out onto a clean work surface and finish bringing it together by hand or with a flexible bench scraper. Roll it out to about ½” thick and transfer it to the prepared half-sheet pan. (It will not fill the pan.) Cover it tightly with a piece of plastic wrap and chill in the refrigerator for at least 1 hour (or until firm), or overnight.

To make the Oreo filling:
Whisk together the sugar, black cocoa, and salt in a medium bowl. Pour in the melted butter and mix together with a wooden spoon until incorporated. Stir in the egg, yolk, and vanilla. Fold in the flour with a rubber spatula; the mixture will be very thick and nearly black in color.

To assemble & bake the hamantashen:
When you’re ready to roll and cut the dough, preheat the oven to 350°F and place a rack in the center position. Line a rimless cookie sheet with parchment paper. Remove the dough from the fridge and let it soften for 5-10 minutes.

On a lightly floured work surface, roll the dough out to a thickness of about ⅛”, flouring and moving the dough around as needed to avoid sticking to the work surface and rolling pin. (I didn’t find it to be exceptionally sticky to begin with.) If making a double-batch, work with half of the dough at a time.

Cut out circles with a 3″ round cutter and transfer them to the prepared cookie sheet. Try to cut them out as closely as possible to avoid having a lot of scraps. Re-roll the scraps and repeat until you’ve filled the cookie sheet. If the dough has warmed up and softened too much, place the pan in the freezer for 5 minutes to chill the dough circles. (You can put any warm dough scraps in the freezer for a few minutes to firm up.)

Drop ½ teaspoon chocolate filling in the center of each circle; a spring-loaded melon-baller yields a perfectly-sized portion. Do not be tempted to put in more filling– the cookies will spill over or open up in the oven.

To create the hamantashen triangle shape, use your fingers to curve up the edges of each circle to meet at three points. Gently press the corners together to seal the edges together, leaving the top open for the filling to peek out. Place them on the prepared baking sheet. If the cookies are very soft, put the pan in the freezer for 5 minutes.

Bake the hamantashen for about 15-16 minutes, or until the filling is puffed and the cookies are firm, rotating the pan halfway through baking. Set the pan on a wire cooling rack to cool completely.

Store the cookies in an airtight container at room temperature for up to 2-3 days.

© Dafna Adler & Stellina Sweets, 2020.

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