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Brownie-Filled (& Gluten-Free) Hamantaschen

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Depending on who you ask, hamantaschen are made either with a flaky pastry or a simple sugar cookie dough. Either way, they're not usually gluten-free nor are they normally filled with chocolate chip brownie batter!

Chocolate Hamantaschen
Chocolate Hamantaschen

This year, I’ve opted to throw tradition to the wind on both accounts: gluten-free (but delicious) sugar cookie dough made with a little cream cheese and oat flour—for lovely notes of caramel flavor and a golden brown crunch at the edges. And stuffed with lots of chocolate.


Both the dough and filling are soft, so the cookies relax into a lovely low-profile shape in the oven: They might not stand at attention quite like your bubbie’s, but they are beautiful and delicious and new.

Feel free to reinstate a little tradition by swapping in your favorite poppy seed, prune, or apricot filling (or any other) in lieu of my chocolate chip brownie batter. I’m crazy about poppy seeds myself, and daydreaming about a filling made of spiced figs, too!

The Best Strategies for Rolling Out Pie Crust and Cookie Dough
The Best Strategies for Rolling Out Pie Crust and Cookie Dough

The recipe includes a great technique for making cutout cookies, and in particular for working with a soft sticky dough such as this one:


Rather than making the dough, then chilling, then rolling out, only to find that it is too soft to cut and must be chilled again, I roll the soft sticky stuff out immediately between parchment and plastic wrap (so easy), then chill the rolled-out dough long enough to rest and hydrate and become firm enough to cut out my cookies and to transfer them to the baking sheet.

If at any time the dough gets too soft to handle, I slip it into the fridge for a few minutes. This means no floury mess on the counter from rolling out dough, no unwanted addition of flour to the dough, less frustration, and more steps than can be done ahead.

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Chocolate Hamantaschen

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Makes 20 to 24 three-inch cookies or 24 to 30 two and a half-inch cookies

For the dough:

  • 1 3/8 cups (140 grams) oat flour
  • 3/8 cup (56 grams) rice flour
  • 3/4 cup (150 grams) sugar
  • 1/4 teaspoon salt
  • 1/8 teaspoon baking soda
  • 7 tablespoons (100 grams) unsalted butter, softened
  • 3 tablespoons (40 grams) cream cheese
  • 1 large egg
  • 1 teaspoon pure vanilla extract

For the filling:

  • 6 tablespoons (85 grams) unsalted butter
  • 4 ounces (115 grams) unsweetened chocolate, coarsely chopped
  • 3/4 cup (150 grams) sugar
  • 1 teaspoon pure vanilla extract
  • 1/4 teaspoon salt
  • 2 large eggs, cold
  • 2 tablespoons (20 grams) white rice flour
  • 2/3 cup (115 grams) semisweet chocolate chips
  • 1 whole (or partial) nutmeg, optional, for topping
Go to Recipe

What's your favorite filling with hamantaschen? Tell us in the comments below!

Tags: hamantaschen, purim, jewish, jewish holidays