10 Days of Hamantashen, Day 3: Ugly-Delicious S’mores Hamantashen


Italians have a cookie called brutti ma buoni, which means ‘ugly but good’. They are meringues with nuts or chocolate chips folded into them, and they have nothing whatsoever to do with Purim, hamantashen, or Judaism in any way; the only thing they have in common with these Ugly-Delicious S’mores Hamantashen is just that– they are both ugly and delicious. I previously tried a version of S’mores Hamantashen several years ago, and they were tasty, but… so, so ugly. (Also, my photography skills at the time, shall we say, left something to be desired.) I had high hopes that this version based on Uri Scheft’s magical almond shortbread dough would have a different outcome; this is one of the first dough flavors that I tinkered with more extensively than simply adding a spice or mix-in. I hypothesized that substituting brown sugar and a little honey for the white sugar, along with a hefty dose of graham cracker crumbs would yield the familiar flavor I was aiming for. Alas, things did not go exactly according to plan… The first batch was downright ghastly– some of them had more filling on the outside than the inside! But boy were they yummy. The tricky part was that the dough is softer than the other hamantashen doughs because of the honey and wetter sugar, and because the marshmallow fluff filling doesn’t have any structure to keep the cookie dough from collapsing onto itself, they ended up being flattish, twisted, and generally unsightly. Fortunately they were freaking delicious– all graham-y and marshmallow-y, which you might have guessed is what I’m going for here. I almost threw out the rest of that batch of dough and filling because they were too ugly to serve (a baking girl has a reputation to uphold and all), but I figured I could just put out a plate at work and not acknowledge responsibility for them– they’d get eaten after all. But then a happy accident happened– I stuck the second tray of filled and shaped cookies in the fridge while I had to go do some something else, and I kinda forgot it in there. That second tray was very firm from its longer chilling time… and the dough held up much better in the oven!


So that was a big improvement, but I felt like I could do even better– they were almost there. I posited that if I were to add more graham crackers to the dough (I also reduced the initial amount of flour in the recipe to account for the additional dry ingredients from the crumbs), it would help produce a stiffer dough that could hold up to the heat a bit better. This did work, but the trade-off is that the dough is more finicky than the regular almond shortbread, or any other of my variations, for that matter. It needs more babying to prevent sticking and tearing; but I’m here to tell you that it’s 100% worth it, because this dough is utterly graham-tastic! You’ll need to freeze the unbaked cookies for about 15 minutes before baking, which helps them maintain their best shape. That being said, they are still the ugliest hamantashen I’m making this week, as you can see above!

A couple of tips about the marshmallow filling: 1) Do not overfill the hamantashen, tempting as it may be. It does not look like a lot, but it’s just right, as it will expand during baking. 2) Torch the tops of the cookies immediately when they exit the oven. The filling will deflate a bit, but if you toast the marshmallow right away, the tops tend to stay more or less in place.

Start here for the beginning of “10 Days of Hamantashen”. Next up are savory Za’atar Feta Knishentashen!


Ugly-Delicious S’mores Hamantashen
Yields 30-45 cookies

For the graham-almond shortbread (started with the dough from Breaking Breads by Uri Scheft, but somewhat far removed from it now):

  • 2¾ cups (330g) flour all-purpose flour
  • 1 cup + 2 tablespoon (130g) finely ground graham cracker crumbs
  • 50 (½ cup) grams blanched almond flour
  • 1 teaspoon fine salt
  • 230 grams (2 sticks/1 cup/8 ounces) cold unsalted butter
  • 100 grams (scant 1 cup) confectioners’ sugar
  • 3 tablespoons dark brown sugar
  • 1 tablespoon mild honey
  • 1½ large eggs, beaten, at room temperature

For the filling:

  • 2 cups (200g/7 ounces) marshmallow fluff
  • 1 cup (170g) mini chocolate chips

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

Whisk together the all-purpose flour, almond flour, graham crumbs, and salt in a bowl and keep it nearby.

Lay a piece of parchment paper on your work surface and place one 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, brown sugar, and honey 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 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 the parchment paper on your work surface and finish mixing it by hand or with a flexible bench scraper; it will be quite stiff. Transfer the dough to the prepared sheet pan and flatten it out with your hands or a small rolling pin to a thickness of ½-inch. Cover it tightly with a piece of plastic wrap and chill in the refrigerator for at least 6 hours or overnight.


To make the filling:
Combine the marshmallow fluff and mini chocolate chips in a medium bowl and mix together with a wooden spoon until incorporated.

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

Scoop ½ teaspoon of the marshmallow-chocolate chip 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 (they will already do this to some degree).

To create the hamantaschen 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. Transfer the pan in the freezer for 15 minutes to chill the cookies.

Bake the hamantashen for about 12-15 minutes (mine took 13 minutes), or until the corners are lightly golden, rotating the pan halfway through baking. Set the pan on a wire cooling rack and immediately pass a kitchen torch over the exposed the marshmallow filling to toast it. Allow the cookies to cool on the pan for about 10 minutes, then move them directly to the rack.

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


© Dafna Adler & Stellina Sweets, 2020.


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