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Home » Blog » Recipes » Breads » Cinnamon Roll Challah
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Cinnamon Roll Challah

jewlish by jamie handwriting text over a table with meal ingredients scatteredJewlish by Jamie • Oct 7, 2019
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This cinnamon roll challah bread is sweet and stringy on the inside with a crisp crust on the outside. Our all-time favorite challah!

This is a fun way to make your challah dough right on your countertops.  But you can use the same filling with any challah dough.  For more incredible challahs, check out our famous Jamie Geller’s Challah or our super-easy No Knead Challah.

When this cinnamon roll challah is in the oven the house will smell amazing. 

Cinnamon Roll Challah

This cinnamon roll challah bread is sweet and stringy on the inside with a crisp crust on the outside. Our all-time favorite challah!
Prep Time 20 minutes mins
Cook Time 30 minutes mins
Total Time 3 hours hrs
Print Recipe Pin Recipe

Servings

6 Servings

Ingredients

  • 3 ½ cups all-purpose flour
  • 2 eggs and 1 more for egg wash
  • 2  ¼ teaspoons active dry yeast 1 packet
  • 3 tablespoons honey
  • ⅓  cup extra virgin olive oil
  • 1 teaspoon salt
  • ⅔  cup warm water
  • ⅓  cup canola oil
  • ¾  cup brown sugar1 ½ teaspoons cinnamon
  • pinch of salt

Instructions

  • For this recipe, we make the dough on the counter because it’s fun and you don’t need to wash a huge bowl afterwards. Place the flour in the center of your table and make a hole in the center like a crater in the top of a pyramid.
  • In the center of the flour, add the eggs, yeast, honey, oil, salt and half of the water. Mix with a fork. Then using a spoon or your hands pull some of the flour from the edges into the center to form a dough. Add the remaining water while there is still a bowl shape in the flour. Mix into a dough and knead for 7 minutes. Cover and allow to rise for 1 hour in a warm place.
  • While the dough is rising, make the filling a medium sized bowl. Add the oil, sugar and cinnamon. Mix.
  • Preheat the oven to 375°F/190°C. Separate the dough into 3 pieces. Roll each one into a square with a rolling pin. It helps to flip the dough and pull the corners with your hands. If you rip the dough, simply patch it with your fingers. Spread the cinnamon-sugar mix on the dough, leaving a 1/2 inch around the edges. Roll each square. Pinch the ends and stretch each strand to about a foot long. Braid them up! Place on a non-stick baking surface and cover for 30 minutes.
  • Gently brush the challah dough with one beaten egg. Bake for 30 minutes. If the top is getting too dark, place a piece of foil on top of the challah in the oven.
Category: RecipesVideosBreads
Cuisine: Jewish
Holidays: New Year'sShabbat
Diets: PareveVegetarian
Styles: Bake
Tags: Challah
jewlish by jamie handwriting text over a table with meal ingredients scattered

About Jewlish by Jamie

Jewlish by Jamie brings you the most delicious Jewish food from around the world. Founded in 2016, Jewlish by Jamie has reached over 200 million people with our original Facebook video series. Fun, easy and authentic cooking is what we’re all about. With every video we share kitchen hacks and quick cooking tips that will make it easy for you to recreate our recipes in your home kitchen.  Now you can take the best of our recipes into your home with our Jewlish by Jamie Cookbook, buy your copy now. 

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Comments

  1. Eric

    Jun 15, 2026 at 12:30 am

    Can it be made with gluten free bread flour?

    Reply
    • Avatar photoTamar Genger MA, RD

      Jun 15, 2026 at 4:59 pm

      I don’t recommend it.

      Reply
  2. Susanna

    Apr 4, 2026 at 7:28 pm

    5 stars
    Super fun recipe!!! I just took my out of the oven and it’s beautiful. I made mine round, so I coiled the braided dough just before baking. It has that lacquered brown crust that is so iconic with challah. Very easy recipe, though I did knead longer than called for because it was very sticky after 7 minutes, so I added about a half cup of flower while kneading. I also added raisins to the cinnamon sugar.

    Reply
  3. Debra

    Feb 18, 2026 at 8:48 am

    Can the dough be made i a bread oven?

    Reply
    • Avatar photoTamar Genger MA, RD

      Feb 24, 2026 at 12:10 pm

      We haven’t tried it but I think so.

      Reply
  4. cindy

    Apr 27, 2022 at 3:40 am

    Can I omit cinnamon and just make regular challah from this recipe?

    Reply
    • Tamar Genger MA, RD

      Apr 28, 2022 at 11:05 am

      We have tons of challah recipes so if you just want a plain one I might suggest one of the others, but you can do it.

      Reply
  5. Tamar Genger MA, RD

    Jul 24, 2020 at 8:04 am

    You can let it go for 2 hours if the temp is a little cooler, not quite the fridge but not too warm.

    Reply
  6. Alanna Wiest

    Jul 23, 2020 at 10:53 pm

    can I let this rise for two hours or will that ruin the recipe?

    Reply
  7. Alanna Wiest

    Jul 23, 2020 at 10:53 pm

    Hi, could I let this rise for two hours or will that ruin the recipe?

    Reply
  8. Tamar Genger MA, RD

    Jun 15, 2020 at 7:01 pm

    Sure

    Reply
  9. Hannah Plotnek

    Jun 15, 2020 at 6:39 pm

    Can you use canola oil instead of olive oil for the first part?

    Reply
  10. Tamar Genger MA, RD

    Jun 14, 2020 at 11:38 am

    I think it should work in a bread maker and it can be halved.

    Reply
  11. Malkie Lipton

    Jun 10, 2020 at 2:29 pm

    Can you substitute chocolate for cinnamon? Not a big cinnamon roll fan. Or tahini and Honey?

    Reply
  12. leslie hoddeson

    Jun 10, 2020 at 2:11 pm

    Can this made in a breadmaker? Also, can it be halved?

    Reply
  13. Sabzie

    Apr 1, 2020 at 8:18 pm

    Made it, and the recipe turned out fantastic…My boyfriend loved it!

    Reply
  14. [email protected]

    Nov 8, 2019 at 8:51 am

    For sephardi Jews this would be mezonot. It sounds like a nice cake. We eat our challa with the fish and salads so sweet just doesn’t make it.

    Reply
  15. Tamar Genger MA, RD

    Feb 17, 2019 at 9:09 am

    It’s best to ask your Rabbi there are different opinions.

    Reply
  16. avigal

    Feb 17, 2019 at 4:09 am

    this recipe is amazing! just not sure what bracha should be recited on the challah? is it mezonot or hamotzi?

    Reply
5 from 1 vote

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