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Irish Cream Brownie Hamantashen

Every year after the holidays, I think things are going to quiet down on the baking front… but then there are fresh, bright, citrusy delights to make in January… then luxurious, chocolaty things in February… and surely in March I can take a breather, right?? Of course not, silly— it’s hamantashen season!! This is one of my favorite baking seasons because I have a possibly-overboard amount of fun thinking up new flavors. Which tends to lead to multiple variations and dozens upon dozens of cookies to share; rarely will I make a plain dough with traditional fruit or poppy filling! This, let’s say, “enthusiastic” quantity was slightly problematic during quarantine, since I was left unsupervised with waaayyy too many hamantashen before I could safely get them out the door to friends. Fortunately this year I’m able to take them to work, plus I ran a bake sale to raise money for Ukraine, so this feels like extra positive work. Also, it’s particularly apropos at this moment because the holiday of Purim is all about celebrating triumph over adversity.

Also! My other favorite reason to bake in March is of course St. Patrick’s Day! And this year these two celebratory occasions happen to fall on the same day, which I cannot recall happening in my lifetime. So naturally there had to be a hybrid dessert, which is where these Irish Cream Brownie Hamantashen come in!

I knew that I wanted to incorporate chocolate and Bailey’s Irish Cream in some way, preferably in both the dough and filling, which worked out deliciously well. I used my regular almond shortbread dough based on Uri Scheft’s amazing dough from Breaking Breads, into which I mixed Bailey’s, micro chocolate chips, and crushed green sprinkles. Guittard makes these tiny, tiny chips, which can be ordered online, or if you don’t want to do that, you can try chopping up regular/mini chips or pulsing them in a food processor so that they’re small enough to be incorporated pretty smoothly into the dough rather than being lumpy. As for the sprinkles, something unexpected and funny happened here– I was envisioning a golden dough with light and dark green flecks, similar to my multi-colored Confetti Cheesecake Hamantashen. But when I mixed the sprinkles into the dough, the crushed dust turned the dough green! I didn’t dislike it per se, it just wasn’t what I had expected, resembling mint chocolate chip ice cream. 😂 I think whether or not this happens with your dough depends on the brand of sprinkles that you use. These green ones were purchased from a different source than my regular rainbow sprinkles, which do not bleed. If you prefer the dough to be green and your sprinkles don’t do the trick, feel free to add a couple of drops of green gel food coloring to your dough, but be careful not to overmix. Personally I think the golden-hued dough with green bits would be really pretty, so I may play around with these further. At any rate, it doesn’t affect the flavor of the cookies, and there’s no mint or anything else “green” in the dough.

For the filling, I used my favorite hamantashen brownie mixture from some past flavors, which I amped up with Irish cream liqueur. You can also drizzle a little chocolate ganache on top of the baked hamantashen, but I thought that might be a little overkill for an already highly nontraditional flavor! Instead I sprinkled a little more of the crushed sprinkles over the brownie peeking out of the centers just before baking.

I hope you have a lot of fun with these Irish-themed hamantashen– Happy Purim and St. Patrick’s Day!

Irish Cream Brownie 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):

  • 75g grams (6 tablespoons) green sprinkles, divided (I like using half-and-half light and dark green shades)
  • 400 grams (3 cups + 2 tablespoons) all-purpose flour
  • 50 grams (½ cup) blanched almond flour
  • 65g (⅓ cup) micro chocolate chips, or crushed chocolate chips
  • 1 teaspoon fine salt
  • 225 grams (2 sticks/1 cup/8 ounces) cold unsalted butter
  • 100 grams (scant 1 cup) confectioners’ sugar
  • 50 grams (¼ cup) granulated sugar
  • 1½ large eggs, beaten, at room temperature
  • 1 teaspoon Irish cream liqueur, such as Bailey’s
  • ½ 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
  • 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
  • 2 tablespoons Irish cream liqueur, such as Bailey’s
  • ¾ cup (90g) all-purpose flour

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

Place the green sprinkles in a plastic ziplock bag and smash them into different sized pieces with a meat mallet or other hammer-like utensil. I like to have some “dust” and a few intact pieces, with mostly small in-between bits.

Whisk together the all-purpose flour, almond flour, 65g (about 5 tablespoons) of the crushed sprinkles, the tiny chocolate chips, and the 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, Irish cream liqueur, 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 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, 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, Irish cream liqueur, 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 hamantaschen:
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, cut off pieces of dough as needed with a sharp knife or bench scraper. Repeat the process until all the dough has been rolled out.

Cut out circles with a 3″ round biscuit or cookie 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.)

Scoop or spoon about ½ teaspoon brownie filling in the center of each circle; a spring-loaded melon-baller yields a perfectly-sized portion when filled with a rounded scoop. Do not be tempted to put in more filling– it will cause the cookies to open up in the oven.

To create the hamantaschen 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, leaving the top open for the filling to peek out. Sprinkle a pinch of the remaining crushed green sprinkles over the tops of the cookies. Place them on the prepared baking sheet. If the cookies are very soft, put the pan in the freezer for 10-15 minutes.

Bake the hamantaschen for 8 minutes, then rotate the pan 180° and bake for another 6-8 minutes until the corners are lightly golden. Set the pan on a wire cooling rack to cool completely.

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

© Dafna Adler & Stellina Sweets, 2022. 

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© Dafna Adler & Stellina Sweets, 2022. Unauthorized use and/or duplication of this material without express and written permission from this blog’s author/owner is strictly prohibited. This includes recipes, photos, and all other original content. Excerpts and links may be used, provided that full and clear credit is given to Dafna Adler and Stellina Sweets with appropriate and specific direction to the original content.

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