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These Chocolate Rugelach are incredibly tender and flaky, thanks to the cream cheese-based dough. These refined sugar-free and gluten-free rugelach are filled with dark chocolate shavings for an irresistible holiday treat.

Chocolate Rugelach (Gluten Free + Refined Sugar Free)

  • Author: Rachel Conners
  • Prep Time: 180 minutes
  • Cook Time: 25 minutes
  • Total Time: 205 minutes
  • Yield: 48 cookies 1x
  • Category: Dessert


  • 1½ cups (144g) almond flour
  • ½ cups (56g) tapioca flour
  • 3 tablespoons coconut sugar
  • ¼ teaspoon salt
  • ½ teaspoon cinnamon
  • ¾ cup unsalted butter (slightly softened, cut into small pieces)
  • 1 (8 oz.) package cream cheese (slightly softened, cut into small pieces)

For the filling

  • 8 oz. dark chocolate (chopped very finely)
  • Milk (to brush on top of cookies)


  1. In a the bowl of a stand mixer, combine the almond flour, tapioca flour, coconut sugar, salt, and cinnamon on low until mixed.
  2. Add in the butter and cream cheese and mix on low speed. The dough will get crumbly and then start to come together. Mix until the dough is just combined – some small bits of butter are okay. This can also be done in a bowl with a pastry cutter and wooden spoon, if you don’t have a stand mixer.
  3. Shape the mixture into a large rectangle. Wrap the dough in plastic wrap and chill for at least 2 hours or up to 1 week.
  4. When ready to prepare the cookies, preheat the oven to 350°F.
  5. Cut dough into 4 equally-sized pieces. Sprinkle your rolling surface with tapioca flour (or in between sheets of parchment paper) and roll out one piece of dough at a time into a 12-inch by 4-inch rectangle. Sprinkle 1/4 of the finely chopped chocolate evenly on the dough and lightly run your rolling pin over the chocolate to press it into dough.
  6. Working from the long end, gently roll the dough into a 12-inch long log. You can use a bench scraper to help you lift and roll the dough more easily. Once it’s all rolled up, make sure the seam is at the bottom. Place in the freezer for 15 minutes to firm up the dough (this will also help you make cleaner cuts. You can also wrap the dough plastic wrap and freeze for up to 3 months at this point).
  7. Remove from the freezer. Brush the dough log with milk. Cut each log into 12 equal pieces, about 1” each. Place upright on lined baking sheets.
  8. Bake each sheet individually for 22-25 minutes or until lightly golden. Cool on wire racks. Store in airtight containers – they also freeze really well.