• Leanne Maala - For Micah Siva

Cinnamon Roll Challah

Updated: May 15

Homemade Cinnamon Roll Challah that’ll make you feel like you’re at a Sunday morning brunch!

If you love the taste of cinnamon rolls and you love Challah bread, then you will absolutely adore this recipe. It has all that sweet cinnamon goodness but in a wonderfully soft, dense baked loaf that pairs well with everything (I like mine with cream cheese frosting!)

Bake up this light and fluffy Cinnamon Roll Challah bread recipe- your kitchen smelling absolutely amazing’s a pretty neat bonus too.

Scroll down below for the full recipe! 📝


Cinnamon Roll Challah

Author: Micah Siva

Makes 2 medium sized challahs (in 8 or 9 inch skillets)


  • 1 package instant yeast

  • 1 tbsp sugar

  • 1 ½ cup lukewarm water, divided

  • 3 large egg yolks, egg whites reserved for brushing on top

  • ¼ cup maple syrup or honey

  • ¼ cup butter, melted

  • 1 tbsp vanilla extract

  • 2 tsp sea salt

  • 4 ½ -5 cups all purpose flour

  • 2 tbsp coarse sanding sugar, to sprinkle before baking 


  • ¼ cup butter, softened

  • ¼ cup brown sugar

  • 2 tbsp tahini

  • 1 tbsp cinnamon

Egg wash:

  • 1 egg, whisked

  • Coarse sugar


  1. Combine yeast, sugar, and ½ cup water in a bowl of a stand mixer. Let sit for 5-10 minutes, or until the yeast starts to foam or “bloom”. **if the yeast does not bloom, you may need to get fresher yeast**

  2. Add remaining water, egg, egg yolks, honey, oil and salt, mixing on low to combine. Replace the paddle for the dough hook.

  3. Add flour, one cup at a time, mix on low using the dough hook. Knead the dough until smooth and no longer sticky, adding more flour as needed. Transfer to a clean, oiled bowl. Cover with a clean, damp towel, and let rise until doubled in size, about 1 hour.

  4. Preheat the oven to 350F. Line a baking tray with parchment paper, or grease a 9-inch cast iron pan.

  5. Punch down dough to remove any air bubbles, and transfer to a floured surface.

  6. Cut into 6 even pieces. Roll each piece into a rope, approximately 12 inches long. Cover with a damp cloth and let rest for 10-15 minutes.

  7. Meanwhile, make the filling: combine the butter, sugar, tahini and cinnamon. 

  8. Flatten the dough strands with your fingers, place a line of filling in the center, and pinch to seal. Braid the ropes into 2 braids of 3 strands each. Coil into a circle, and pinch together.

  9. Make the egg wash: whisk together egg and water. Brush with egg wash, and top with coarse sugar (optional)

  10. Bake in a cast iron pan or baking tray for 40 minutes, turning the tray halfway through and brushing with additional egg wash.

  11. Serve with optional cream cheese frosting.

Note: make the second half of dough into regular braid if you don't have two skillets

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