Chocolate Hamantaschen

March 18, 2016

Test Kitchen-Approved

Author Notes:

These are gluten-free and filled with chocolate chips and bittersweet brownie batter. Soft sticky dough like this is best rolled immediately, between parchment and plastic wrap, and then chilled on a cookie sheet for several hours to hydrate and firm the dough before cutting out the cookies! Hint: You don’t need to clear space in the fridge for cookie sheets, just arrange items of similar height together and slide the cookie on top of them.

Alice Medrich

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
In This Recipe


  1. To make the cookie dough, put the oat and rice flours, sugar, salt, and baking soda in the bowl of a food processor fitted with the steel blade. Pulse to blend. Add the butter, cream cheese, egg, and vanilla. Process until well blended: The mixture may come to a ball before it begins to spread out again in the bowl. The dough will be very soft and sticky.
  2. Scrape half of the dough onto a sheet of parchment paper and spread it roughly. Cover with a large sheet of plastic wrap. Use a rolling pin and very gentle pressure to roll and smooth it to an even thickness of 1/8-inch. Slide the dough (including the parchment and the plastic wrap) onto a baking sheet and refrigerate for at least 2 hours, preferably overnight. Repeat with the remaining dough and slide it on top of the first piece.
  3. Meanwhile, to make the filling, melt the butter with the unsweetened chocolate in a stainless steel bowl set directly in a wide skillet of almost simmering water. Stir frequently until the mixture is melted and smooth. Remove the bowl from the skillet. Stir in the sugar, vanilla, and salt. Stir the eggs in one at time. Stir in the rice flour. Stir briskly with a spatula until the mixture is thick and smooth and glossy pulls away from the sides of the bowl. Let cool. Stir in the chocolate chips. Refrigerate until needed.
  4. Position racks in the upper and lower thirds of the oven and preheat the oven to 325° F.
  5. Remove one sheet of dough from the fridge. Flip it parchment side up. Peel off the parchment and place it on the counter next to the dough. Grasp the plastic wrap and flip the dough back onto the parchment. Peel off the plastic wrap. Working quickly, cut out 3-inch or 2 1/2 –inch cookies and place them 1/2 inch apart on the lined pans. (If the dough becomes too soft to handle, slide it onto a pan and return to the fridge to firm up.) For 3-inch cookies, scoop and place a heaping (13-gram) teaspoonful of filling in the center of each cookie; for 2 12-inch cookies use a rounded teaspoon (11 grams). Bring 3 sides of each cookie up to partially cover the filling and press the edges together to seal them—the dough is quite sticky so that the seam will not open up in the oven! If the dough gets too soft to handle, put the pan in the fridge to firm it up. Repeat with the second sheet of dough.
  6. Bake for 20 to 25 minutes, or until the cookies are golden brown. Rotate the pans from top to bottom and front to back about halfway through the baking time to ensure even baking.
  7. While the cookies are baking, press all of the dough scraps together and reroll them between parchment and plastic wrap. Chill until firm enough to cut and fill. Since there is no gluten in the dough, you can reroll scraps as many times as you like without making the cookies tough.
  8. Set the pans, or just the liners on rack to cool. I like to serve them with a little nutmeg grated directly over the top. Cool cookies completely before stacking of storing. Cookies are best on the day they are made, but they keep for 2 to 3 days in an airtight container.

More Great Recipes:
Cookie|Chocolate|Cream Cheese|Oat|Nutmeg|Spring|Dessert

Reviews (2) Questions (2)

2 Reviews

Anita104 March 12, 2017
Could the filling for these be baked on its own?
Heather M. March 24, 2016
While the chocolate filling looks delicious, could you also fill it with the classic jam or poppyseed filling?