Chocolate Orange Challah

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Wei and Leili of Yin and Yolk

With this decadent recipe, take your challah to the next level (and the next course) by having it for dessert.

Yields:

1

Ingredients
Dough
3 1/2 tsp.
active dry yeast
1/3 c.
+ 2 tbsp orange juice
Large orange, zested
1/3 c.
olive oil
1/2 c.
honey
2
eggs plus 1 yolk
1 1/2 tsp.
salt
4 1/4 c.
all-purpose flour
1
egg
Filling
4 1/2 oz.
bittersweet chocolate
4 oz.
unsalted butter
1/3 c.
granulated sugar
2 tbsp.
cocoa powder
Directions
  1. Heat or microwave orange juice to room temperature. In
    the bowl of an electric stand mixer, combine yeast and orange juice and
    stir to dissolve, then add honey, zest, oil, and eggs and yolk. In a
    separate bowl, mix together salt and flour, transfer to mixer with hook attachment and knead on medium for 10 to 15 minutes.
  2. Oil a separate bowl and transfer dough to it. Let sit, covered at room temperature, about 1 hour, then refrigerate overnight. 
The next day, gently press down dough and flip over in its bowl, re-cover, and let come back to room temperature.
  3. Meanwhile, make the filling. Melt together butter and chocolate; mix in granulated sugar and cocoa powder until combined. (It should be runny – a little graininess from the sugar is expected.) Let sit at room temperature while you ready dough.
  4. 
 Transfer dough to lightly floured surface and divide into two equal parts. Set one half aside, and gently press or roll the other into a wide rectangle about 15”-x-10” and 1/4” thick. Spread half chocolate filling all the way to the sides of the dough on the right and left, leaving a 1/2″ to 1” space on the top and bottom edges. From the bottom edge closest to you, begin rolling up the dough (like cinnamon rolls). When you get near the end, wet the top 1/2” of dough and spread it thinly across your work surface–this will make it easier to adhere to the other side of the roll. Roll it up and smooth out the edge, then set aside to rest. Repeat with the other half of the dough, and let the two logs rest for another hour, covered loosely by plastic wrap or a dish towel.

  5. Cut each log in half lengthwise. With chocolate
    stripes facing up, make a plus sign
    with two of the logs. Loosely weave the other two logs into this plus sign.
    Then, loosely take both ends of one side of the plus sign and cross them over
    each other. Do this to all sides of the plus sign, then do it again, and again,
    alternating going over and under, until you’re left with almost a round, then
    tuck the ends underneath the loaf. Keep it loose enough for the bread to
    have room to rise in the oven, but not so loose that there are visible spaces between the strands of dough.
  6. Cover with a towel and let sit until puffy, about 2 hours. Brush with egg
    wash and let rise 1 hour more.
  7. Preheat oven to 375 degrees F, then brush loaf again with egg wash before putting into the oven. Bake 35 to 45
    minutes, but check on it around the 25- to 30-minute mark. If it’s getting dark
    too quickly, cover with foil for remainder of cooking time.
  8. When a thermometer reads an internal temperature of 195 degrees F (or
    when it looks bronzed and sounds a bit hollow when you tap on it),
    it’s done. Let cool completely on a wire rack before slicing.