10 Days of Hamantashen, Day 5: Mexican Chocolate Hamantashen


This hamantashen flavor is brought to you by the letters ‘S’ and ‘D’, as in ‘San Diego’. Last winter when I returned from living in Israel sooner than expected, I was lucky to be able to crash in San Diego for a few months with my good friends. I honestly don’t know what I would have done during that time if not for their generosity and openness. One way that I hoped to add value to their home while I was there was cooking as much as possible, especially because they were so busy with full-time work and a toddler. And of course… it was awesome to have people under the same roof to bake for! So naturally when March rolled around, I had to introduce them to hamantashen. I wanted to make a flavor that they would especially appreciate, and since they love Mexican food (plus Mexican cuisine is part of the fabric of San Diego), I settled on Mexican Chocolate Hamantashen. The other reason I liked this route was because I’d made a double batch of cinnamon dough, half of which I used for my Cinnamon Dulce de Leche version. I knew it would be perfect with my favorite brownie filling, to which I added cinnamon and cayenne pepper for that warm spiciness characteristic of Mexican chocolate. They are in fact one of my favorite flavors to date, so I had to include them in the 2020 collection.

Start here for the beginning of “10 Days of Hamantashen”. Next is Mexican Chocolate!


Mexican Chocolate 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. (Dough photos below reflect a double-batch.) I strongly recommend using weight rather than volume to measure ingredients, as the original recipe favors weight.

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

  • 3 cups + 2 tablespoons (400 grams) all-purpose flour
  • ½ cup (50 grams) blanched almond flour
  • 2 teaspoons ground cinnamon
  • 1 teaspoon fine sea salt
  • 16 tablespoons (2 sticks/1 cup/230 grams) cold unsalted butter
  • Scant 1 cup (100 grams) confectioners’ sugar
  • ¼ cup (50 grams) granulated sugar
  • 1½ large eggs, beaten, at room temperature
  • 1 teaspoon pure vanilla extract or vanilla bean paste

For the brownie filling:

  • 1 cup (200g) granulated sugar
  • ¾ cup (63g) dark unsweetened cocoa powder, such as Valrhona
  • 1 tablespoon ground cinnamon, or to taste
  • Scant ½ teaspoon ground cayenne, or to taste
  • ¼ teaspoon kosher salt
  • 7 tablespoons (100g) unsalted butter, melted
  • 1 large egg, at room temperature
  • 1 egg yolk, at room temperature
  • 1 teaspoon pure vanilla extract or vanilla bean paste
  • ¾ cup (90g) all-purpose flour

To make the cinnamon 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, cinnamon, 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. (Pounding the butter keeps it cold, but softens the texture.) 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 vanilla, 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 most of the flour has 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 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 brownie filling:
Whisk together the sugar, cocoa powder, cinnamon, cayenne, and salt in a medium bowl. Pour in the melted butter and mix together with a wooden spoon or stiff whisk until incorporated. Stir in the egg, yolk, and vanilla. Fold in the flour with a rubber spatula; the mixture will be very thick. Refrigerate if not using right away.

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. Remove the brownie filling from the fridge if needed and stir to loosen it.

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 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, keeping the unused dough in the fridge until you’re ready for it.

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 also put any warm dough scraps in the freezer for a few minutes to firm up for easier rolling.)

Scoop ½ teaspoon brownie 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. Press the corners together to seal the edges, leaving the top-center open for the filling to peek out. If the dough cracks on the bottom, gently smooth it back together with your fingers. Place the cookies back on the prepared baking sheet spaced a couple of inches apart. If they are very soft, put the pan in the freezer for 5 minutes.

Bake the hamantashen for about 13-16 minutes, or until the corners are lightly golden, rotating the pan halfway through baking. Set the pan on a wire cooling rack for about 10 minutes, then transfer the cookies directly to the rack to cool completely.

Store the hamantashen in an airtight container for up to 3 days or so.




© Dafna Adler & Stellina Sweets, 2020.

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