Adapted from Bon Appetite

*You can replace the soy milk with almond milk and the coconut oil with vegetable oil, but do keep in mind you will lose some of the richness from the dough. Alternatively, you can replace the soy milk with whole dairy milk and the coconut oil with butter, in which case the chocolate Challah will be super rich!


  • 240ml (1 cup) soy milk
  • 14g (5 teaspoons) active dry yeast
  • 8 egg yolks
  • 2 teaspoon vanilla extract
  • 240ml coconut oil, melted, cooled
  • 175g (⅔ cup) granulated sugar
  • 2 teaspoon salt
  • 750g (6 cups) plain (all-purpose) flour, plus more for dusting

Filling and Assembly

  • 350g (12 ounces) bittersweet chocolate, broken up into small squares
  • 135g (⅔ cup packed) light brown sugar
  • 1 tablespoon ground cinnamon
  • 120ml (½ cup) coconut oil, melted, cooled
  • 1 large egg yolk
  • Granulated sugar (for sprinkling)

For the Dough:

Heat soy milk in a small saucepan until warm. Transfer milk to the bowl of a stand mixer fitted with the dough hook, sprinkle in the yeast and let sit until foamy, 5–10 minutes.

To the bowl add in egg yolks, vanilla, and 240ml (1 cup) coconut oil. Add sugar, salt, and flour; turn on the mixer to its lowest setting and let it knead the dough until supple and smooth 5-10 minutes.

Alternatively, you can do this by hand.

Transfer to a large oiled bowl. Cover and let sit in a warm place until doubled in size, 1½–2½ hours.

To fill and assemble:

In the bowl of a food processor, place the chocolate, brown sugar, and cinnamon, process until the chocolate is pulverized and the biggest pieces are no larger than the size of a pea. Divide the chocolate mixture evenly between 6 bowls, about ½ cup (just under 100g) of mixture per bowl. Set aside.

Turn out dough onto a lightly floured surface; divide into 6 portions. Shape each into a 12”-long rope. Roll out each rope to a 12×6” rectangle about ⅛” thick. Brush with coconut oil and top with chocolate mixture, pressing gently. Roll up to form a log; pinch seam to seal. Repeat with the remaining 5 portions of dough.

Place t3 logs, seam side down, side by side on a parchment-lined baking sheet. Pinch logs together at one end; braid, then pinch ends together and tuck under. Cover loosely and let sit in a warm place until 1½ times larger, 1–2 hours.

Preheat oven to 180℃ (350℉). Beat egg yolk with 1 tablespoon of water in a small bowl. Brush dough with egg wash; sprinkle with granulated sugar. Bake until the top is golden brown and Chocolate Challah sounds hollow when the bottom is tapped, 35–45 minutes. Let cool on a wire rack.