Cinnamon Roll Challah Recipe


(makes 2 loaves)


  • 1 1/3 cup water
  • 1/3 cup canola oil
  • 4 egg yolks
  • 2 tsp salt
  • 4 ¼ cup bread flour
  • ½ cup sugar
  • 1 Tbs instant bread machine yeast
  • For the cinnamon roll filling:
  • 6 tablespoons butter or margarine, softened
  • 1 cup packed brown sugar
  • 4 tablespoons cinnamon


  • 1 egg yolk
  • 1 teaspoon water
  • Cinnamon sugar


Add dry and wet ingredients to a bread machine in the order specified by the manufacturer. Set machine for “dough” cycle.

If not using a bread machine, combine all the ingredients in a large bowl, turn out on to a floured board and knead for 5 minutes. Allow to rise in a large bowl in a dark place, covered with plastic wrap or a towel for 1 ½ hours.

While dough is rising, prepare the cinnamon roll filling by mixing the brown sugar and cinnamon in a small bowl.

When the dough cycle is complete, remove dough from the bread machine and divide into 6 equal portions. On a floured surface, roll three portions into long ropes, and using a rolling pin, roll each portion into a rectangle approximately 12 inches long and 8 inches wide. Spread 1 tablespoon of butter on the surface of each rectangle, and then sprinkle 1/6 of the cinnamon filling evenly over the butter.  From the long edge of the dough, gently, but tightly, roll the dough up to the end. Repeat for all 3 rectangles. Carefully braid each of the rolls together, then place on a greased loaf pan or greased cookie sheet. Repeat with remaining dough.

Cover with a towel and let rise for 30-60 minutes in a draft-free place.

Preheat oven to 350 degrees.

Beat egg yolk and mix in water to prepare the egg wash. Brush over each challah, sprinkle with a generous amount of cinnamon sugar.

Bake challahs for approximately 40 minutes or until golden brown. Remove from pans and allow to cool on a wire rack.

Best served slightly warm.

Mandylicious Challah

Mandy Silverman grew up in St. Louis, went to college in Ann Arbor (Go Blue!), stuffed her first challah in Pennsylvania, and created Mandylicious nearly 4 years ago in Sharon, MA. She is eternally grateful for the every day inspiration and support from her husband and two children. Check out what crazy challah innovations she will come up with next at or follow her @Mandyliciouschallah on Facebook and Instagram.