Cinnamon Bun Challah

One of my favorite foods to make (and eat!) is challah.  There are so many variations of this tasty egg bread that it can be made and served sweet or savory.  A few days ago, I decided to aim for the sweet side and made a Cinnamon Bun Challah from my Jewlish Cookbook.  This recipe was a hit among my family and friends–so much so that my mom asked me to make it for her bible study group this weekend!  Check out how to make it below.


Although the recipe doesn’t call for you to put the ingredients in a bowl, I chose to do so because it would make the cleanup less messy.  So I picked the biggest bowl I could find and put in the flour, eggs, yeast, honey, olive oil, salt and half of the water.



I mixed it with a fork for a bit, added the other half of the water, and then used my hands to begin kneading the dough.  Kneading is just a fancy word for stretching and mixing dough with your hands for a few minutes–do not be afraid or turned away by these baking terms.  I found the dough to be a bit watery, so I added extra flour.  Just make sure the dough is not too sticky but not so dry that it doesn’t stay together.


Once you knead the dough for about 5 minutes, place it back in the bowl or on a plate, cover with a towel, and let it rise for about an hour.  I never seem to see my dough “double in size”, as the recipe says it will.  But it will rise a bit.


While it rises, you can make the cinnamon sugar filling.  Take a small bowl and mix together the oil, brown sugar, cinnamon and salt.  The salt felt a little overwhelming to me, so I’d lessen the amount next time.  I also needed to add extra oil because the mixture was too chunky/dry.  Lastly, if you want to add more cinnamon and sugar because you LOVE cinnamon rolls like I do, just do it.


After this mixture is done and the dough has risen, you can now pre-heat the oven and grab your dough to begin the final few steps.  First off, shape your dough into a rough square shape and cut it into three equal sized pieces.


Now take one piece of dough and flatten it into about a 9×9 inch square.


Put 1/3 of the cinnamon on this square and spread it out while leaving about a one inch perimeter of dough cinnamon-free.


Roll up the dough and pinch the ends and edges so the cinnamon doesn’t fall out.  Repeat these steps for the remaining two pieces.  I also squeezed each piece so that the dough sticks together more and stretches out to make for a longer challah bread.


Now it’s time to braid this challah masterpiece, which is where most people get confused.  I forgot to take a video of me braiding but I found a great YouTube video that shows you how to braid a 3-strand challah (LINK HERE).  Only things I would take note from the video is to start the challah braid from the top rather than the middle, as the video shows.  You can pinch together the three strands at the top and then start the braid.  Then, once you finish braiding, take the ends of the strands, pinch them together and push them into the underbelly of the challah so that the ends don’t stick out.  Congrats!  You’re almost done.

Put that beautiful challah on some parchment paper and then on a baking sheet.  Now take an egg, beat it so it’s well mixed, grab a kitchen brush and then liberally apply the egg wash onto the challah.  Make sure you don’t miss any nooks and crannies and the underbelly of the challah.  I threw a few teaspoons of crumbled cinammon sugar on top of the challah too for extra flavor.

Now put the challah in the oven, bake for about 30 minutes and take it out to cool for about 10 minutes (if you can wait that long before diving in to eat it!).  Beteavon!


Ingredients (1 large loaf)


  • 3 1/2 cups all-purpose flour
  • 2 large eggs
  • 2 1/4 teaspoons active dry yeast (1 packet)
  • 3 tablespoons honey
  • 1/2 cup olive oil
  • 1 teaspoon salt
  • 2/3 cup warm water


  • 1/3 cup canola or olive oil
  • 1 cup brown sugar
  • 3 teaspoons cinnamon
  • Pinch of salt


  • 1 egg
  • Cinnamon sugar (optional)


  1. Mix together flour, eggs, yeast, honey, olive oil, salt and half of the water with a fork.  Scrape flour from edges and back into the dough mixture.  Add the other half of the water.
  2. Knead dough with hands for 5 to 10 minutes, or until smooth and not sticky or too dry.
  3. Cover with towel and let dough rise for about an hour.
  4. Make filling while dough is rising.  Mix together brown sugar, canola or olive oil, cinnamon and salt.
  5. Separate dough into three equal pieces.  Use a rolling pin to flatten the first piece of dough into a 9×9 inch square.  Spread 1/3 of the cinnamon mixture on top, leaving 1 inch of space around the edges.  Roll it up and pinch the ends and edges.  Repeat for the remaining two pieces of dough.
  6. Preheat oven to 375F.
  7. Stretch each strand to at least 12 inches in length.  Braid using the 3-strand challah braiding method.
  8. Place braided dough onto a non-stick cookie sheet or onto parchment paper.
  9. Liberally brush with a beaten egg.  Sprinkle cinnamon sugar on top.
  10. Put challah dough into oven and cook for 30 minutes.  If the challah prematurely darkens, place an aluminum foil sheet on top and continue baking for the total 30 minutes.
  11. Remove challah from oven, let cool and enjoy!
Modified from Jewlish Cookbook.

I hope you liked this recipe–look out for the Apple Challah recipe soon!

xoxo Kasia

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