Triple Chocolate Challah Bread

How to Make a Triple Chocolate Challah Bread on Steroids

Nathan Hawkes Nathan Hawkes Mar 07, 2024

This isn't just chocolate challah bread, it's chocolate challah bread on steroids.It's not just braided bread, it's chocolate bread with a fudgy chocolate filling and chocolate frosting.  It's moist and tender.

And when you scroll down, you can see how you can make this with our most popular white bread mix.

Last week, our most popular feature was cherry-filled braided bread. So this week, we brought you a chocolate version--a triple chocolate version.  If you love chocolate, this will blast the cherry version out of the running, not that the cherry version isn't very good.

Key Factors For Success

See the Cherry Braided Bread. This includes step-by-step directions both for filling your bread and braiding the bread dough.

braided bread

Key #1

This is a picture of the cherry bread, Each of the three braids is filled with a cherry pastry filling. The chocolate version has a chocolate filling and a chocolate frosting. They're both rich and fudgy, made with cream cheese. 

Three pieces of dough are rolled out into into a flat rectangle about 1/4-inch thick as if you were making cinnamon rolls. Instead of sprinkling sugar and cinnamon over the flat bread and rolling in pinwheel fashion, chocolate filling is smeared over it like in this cherry picture.  

filled dough braid

Once rolled, the ends and the long seam are pinched together to create a rope with enclosed filling. Do this three times to create three ropes.

Key #2

The second key is the braid.

The ends of the three braids are pinched together to start the braid. Continue the braid as in the earlier image and then, at the end, pinch all three ropes together to complete the loaf.

starting the braid

You can push the ends or pat the sides to adjust the shape of the loaf to make it more cylindrical.  Place it on a prepared baking sheet and cover it with plastic or place the pan with a loaf into a proofing bag and let it rise until doubled. 

This is what the loaf looks like before going in the oven. Notice how large it is on an 11x17-inch pan.

braided bread ready for the oven

You can use different breads and different fillings to make a collection braided breads. Pastry fillings work well with these breads.

Chocolate Braided Bread Recipe

This is scrumptious. Braiding bread is not complicated; it just looks impressive. 

We made this bread from scratch, not from a mix. After these scratch directions, we'll include directions to make this bread using a bread machine mix. 

Again, to see how to fill the braids and then braid the dough, see above and the Cherry Braided Bread.



  • 3 to 3 1/2 cups bread flour
  • 1 packet instant active dry yeast
  • 3/4 cup water, heated to 110 degrees
  • 1/3 cup brown sugar
  • 1/3 cup cocoa
  • 4 tablespoons butter
  • 1/2 teaspoon salt
  • 1 large egg at room temperature


For the filling:

  • 5 ounces cream cheese
  • 1 ounce semi-sweet baking chocolate, melted
  • 3 tablespoons granulated sugar
  • 2 tablespoons all-purpose flour
  • 1 egg yolk
  • 1/2 teaspoon vanilla extract
  • 1/8 teaspoon nutmeg



  1. Mix about one cup of the flour, the yeast, and the heated water until smooth. This will hydrate the instant yeast. If you are using other than instant yeast, hydrate the yeast separately.
  2. Add the brown sugar, cocoa, butter, salt, and egg and mix. Add enough of the remaining bread flour to make a soft but not tacky dough. Knead until the gluten is developed, about four minutes with a stand-type mixer at medium speed. Set the dough in a greased bowl, cover, and let it stand until doubled, about one hour.
  3. To make the filling, beat the cream cheese until soft and smooth. Add the melted chocolate while it is still hot and mix until smooth. Add the sugar, flour, egg yolk, vanilla, and nutmeg and mix until smooth.
  4. Once the dough has risen, use a knife to divide the dough into three equal pieces, as above. Roll the dough pieces with a rolling pin to rectangles 15 inches by 5 inches. Spread one-third of the filling down the center of each leaving a one-inch border with no filling. Roll the rectangle into fifteen-inch long ropes with the filling inside. Pinch any seams together and roll the ropes with your hands on the counter until smooth.
  5. Braid the three ropes as if you were braiding pigtails. (Some people find it easier to create a symmetrical shape if they start braiding from the center.) When you get to the ends, wet them, pinch them together, and tuck them under. You should have a neat, symmetrical loaf when you are through. You can shape the loaf somewhat with your hands. If you don’t like how the loaf looks, simply pull the braids apart and start again.
  6. Prepare a large baking sheet by greasing it and sprinkling it with cornmeal. Place the loaf on the pan, cover the loaf, and let it rise until doubled, about one hour.
  7. Preheat the oven to 350 degrees. Bake the bread for 20 minutes then cover the bread with a large sheet of aluminum foil and bake for another ten to fifteen minutes to until done. The bread should “thump” when tapped on the bottom and the interior of the loaf should register 190 degrees with an insta-read thermometer. Let the bread cool on a wire rack.
  8. While the bread is cooling, make the glaze. With a hand-held mixer, beat one ounce cream cheese with one teaspoon vanilla. Add 1 1/2 cups powdered sugar and 2 tablespoons cocoa with enough warm water to make a glaze of drizzling consistency. Drizzle the chocolate glaze generously over the bread.

Baker’s notes: To quickly bring an egg to room temperature, place it in a cup of warm water.

To make this with a bread mix

Choose a bread mix. Country Farm White Bread is a good, basic mix.You will want to add cocoa and a sweetner.  The resulting dough will be dry and need some extra water.

  1. Empty the mix into a mixing bowl. Add 1/3 cup good quality cocoa and 1/3 cup brown sugar to the other dry ingredients.  Add the yeast. With a whisk, thoroughly blend these new ingredients and  the ingredients from the mix together..
  2. You are now ready to make the dough. You can do so with your bread machine or with your stand-type mixer. If you are going to use your bread machine, set the control on the dough cycle, cycle 8 on most machines. If you are going to use your stand-type mixer, equip it with a dough hook.
  3. Place the dry ingredients (including the yeast) into the bowl of your stand-type mixer or the bread machine pan. Add the water directed by the instructions with your bread mix. Add an extra tablespoon of extra water (to compensate for the extra dry ingredients).
  4. Begin mixing. Soon the ingredients combined with water will form a dough ball.  Stop the machine to check the dough ball.
  5. The dough ball should be soft and sticky. By poking the dough ball with your finger, you should easily form a quarter inch dent.  The dough should be sticky, a wet soft dough ball. If not, you'll need to drizzle in some extra water. (You'll likely need to add more water. Add it carefully. It's easier to add more water than correct your dough if you've added too much water.)
  6. Cover the dough with plastic wrap or place the pan with the dough in a proofing bag. Let it rest in a warm place, covered, for about 60 minutes.

You are now ready to divide, fill, and braid the dough. follow the instructions set forth here and on the cherry braided page.

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