Chocolate Cinnamon Roll Challah

Chocolate cinnamon roll challah crumb

The Magical Combination Of Chocolate, Cinnamon Roll & Challah

The one thing I love about developing sourdough recipe is that I can experiment with every crazy ideas I have in mind. And the best thing is, they usually turn out pretty darn good every single time. 🤩 Ever since I entered the world of rich and spongy enriched dough, I have been trying to make one every chance I get. In case you are new here (Hello and welcome 👋🏻), I have been obsessed with sourdough challah. There is something about the texture of challah that makes it so special and addictive. 😜 It is lightly sweetened, with a dark, shiny crust and a firm but light, buttery and tender texture. After my first try on sourdough challah, I created another challah inspired sourdough recipe. Check out my Matcha babkallah recipe for more challah goodness. Given my previous successful attempts on sourdough challah, it’s time to step it up a notch by combining 3 of my favorite foods – Chocolate, cinnamon rolls and challah. Hence, the birth of this amazing Chocolate Cinnamon Roll Challah recipe!

Chocolate cinnamon roll challah

Yudane Method 💦

This Chocolate Cinnamon Roll Challah have the texture that resemble most Japanese bread – super soft and fluffy. As I learned more about sourdough baking over the past year, I came across the Yudane Method. Yudane method is the secret to make a soft and fluffy Japanese style bread. In order to bake using this method, you simply mix an equal portion of flour and boiling water. The effect of adding boiling water to flour is that it gelatinises the starch. The gelatinised starch will allow the starch to absorb more water, and thus enhancing the sweetness of the bread.

chocolate cinnamon roll challah

Yudane method is in fact similar to the Tangzhong method I used in my sourdough shokupan recipe. Unlike the 1:1 flour-to-water ratio in Yudane method, the Tangzhong mixture is made by heating up a mixture of flour and water in the ratio of 1:5 to 65°C.

For more sourdough recipe using Yudane method, check out my vegan sourdough shokupan and sourdough cinnamon roll recipe.

Take a look at my other recipes using yudane

Stiff Levain

In this recipe, I used a 50% hydration lievito madre as the stiff levain. Using a stiff levain is crucial in this recipe because the tanginess in sourdough starter does not go well with matcha flavor. You can of course convert your 100% hydration sourdough starter to a 50% hydration starter if you don’t have lievito madre. You can learn how to convert your starter by following the recipe below. If you are using lievito madre, remember to refresh at least 3 times (4 hours apart) before using it. You will need 180g of lievito madre for this recipe.


As for the filling, you can use your usual cinnamon roll fillings. The fillings I used here is similar to the one used in my Double Chocolate Babka Rolls recipe. The night before making this challah, soak 1/2 cup of raisins in rum. In the morning, drain the raisins and melt 1/2 cup of chopped chocolates together with 1/4 cup of tahini. Now, for the fun part. Roll your dough into a long rectangle, evenly spread the chocolate mixture, sprinkle rum soaked raisin and cinnamon on top. Then, roll the dough tightly like you do when making cinnamon rolls. And there you have it! 🙌🏻

Baking Schedule

4pm: Prepare Levain
8pm: Mix the dough
8:30pm: Retard in fridge
Next day
8:30am: Shape and braid the challah. Proceed to final proof
12:30pm: BAKE!

Chocolate Cinnamon Roll Challah

Recipe by Angie @ The Floral VeganCourse: SourdoughCuisine: JewishDifficulty: Medium


Prep time


Cooking time



Combining 3 of my favorite foods – Chocolate, cinnamon rolls and challah into one bread! 😋



  • Mix all the ingredients of the stiff levain and leave it to rise until doubled or even tripled. It usually takes 3-4 hours at 82°F (28°C).
  • While you are waiting for the stiff levain to rise, add 100g boiling water to 100g bread flour. Leave it aside to cool completely.
  • Once the levain is ready to use, place all of the ingredients (except oil) into the bowl of your stand mixer. Using the hook attachment, knead for about 5 minutes until the dough comes together and forms a dough ball.
  • Gradually add in oil and continue knead for 10 – 15 more minutes or until reach window pane stage. 
  • Shape the dough into a ball and place in a bowl. Cover and leave the dough in the fridge for 8 to 12 hours.
  • In a small bowl, soak the raisins in 1/2 cup of water and 1/2 cup of rum.
  • The next morning, drain the raisins. Then, melt the chocolate chips using the double broiler method. Mix the melted chocolate with almond butter. Leave it aside to cool for a bit.
  • Now, transfer the dough to a clean floured surface then divide into 6 equal portions. Form each portion into a ball. Let the dough rest for 15 mins.
  • Roll each dough into a rectangle. Gently spread the filling evenly on the dough, leaving a 1/2-inch border around the edges.
  • Using floured fingertips, carefully roll the long side of the dough. Once you get to the end, roll the dough so that the seam side is facing down.
  • Braid the challah. I followed the instructions in this video.
  • Carefully transfer the challah onto a lined baking tray. Brush with “egg” wash.
  • Mark with a pencil about 1.5 cm away from the original size of the dough on both sides.  Let it proof at a warm place until the dough rise double in size or when it reaches the mark.  Mine took approximately 4 hours at 82°F (28°C).
  • Preheat oven at 350°F (175°C). Brush with egg wash again.
  • Bake in a preheated oven for about 35-40 minutes, or until golden brown. Rotate the tray halfway to ensure the challah is evenly baked.
  • Remove challah from oven and let them cool on rack completely.



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