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Soft, pillowy, buttery challah dough is stuffed with warm cinnamon sugar and pockets of gooey chocolate, and topped with a light drizzle of glaze.

Chocolate Chip Cinnamon Challah Rolls

Challah dough is stuffed with warm cinnamon sugar and pockets of gooey chocolate, and topped with a light drizzle of glaze
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Prep Time 30 minutes
Cook Time 20 minutes
Course Breakfast
Servings 8

Ingredients
  

  • 1-1/2 packages active dry yeast
  • ½ cup granulated sugar + 1 tbsp
  • ½ cup vegetable oil can also use avocado oil
  • 5 large eggs
  • 1 tablespoon kosher salt
  • 8 cups all-purpose flour

Filling

  • ½ cup packed brown sugar
  • 1 tsp cinnamon
  • 1 cup semi sweet chocolate chips
  • 3 tbsp unsalted butter softened + 1 tbsp melted

Glaze

  • 1 cup powdered sugar
  • 1 tbsp milk

Instructions
 

  • In a large bowl, dissolve yeast and 1 tablespoon sugar into 1¾ cups lukewarm water.
  • Combine the oil and yeast mixture into the bowl of a stand mixer with the hook attachment or a large mixing bowl using a whisk to mix together.
  • Add 1/2 granulated cup sugar and 4 of the eggs (one at a time) to the mixture until well blended
  • Gradually stir in the flour and mix until a smooth dough is formed (about 2-3 minutes). You can also place dough on a floured surface and knead together for 5-6 minutes until smooth.
  • Remove the dough from the mixer and place in a large bowl coated with oil. Cover with plastic wrap, and let rise in a warm place for 1 hour, until almost doubled in size. It may need a bit longer rise time, depending on the temperature of the area the dough is placed.
  • Pre-heat oven to 350 degrees
  • Punch down the dough and roll out on a lightly floured surface into a 15"wide X 10" tall rectangle
  • Spread 3 tbsp softened butter evenly across the dough
  • Sprinkle the the brown sugar and cinnamon on top of the butter
  • Add the chocolate chips, making sure they are evenly spread over the top
  • Starting from the bottom of the dough, tightly roll up into a log shape.
  • Using a sharp knife, cut dough log into 2"slices, and place them flat down into the pan keeping them close together
  • Cover and allow to rise for 30 minutes
  • Sprinkle 1 tbsp melted butter and 1 tbsp granulated sugar across the tops of the rolls
  • Bake at 350 degrees for 16-18 minutes. Remove from the oven just as they start to turn slightly golden brown. Don't leave them in too long or they will lose the soft fluffy texture.
  • Allow to cool for 15 minutes and add the glaze if using
  • Glaze
  • In a small bowl, mix the milk with the powdered sugar until a thick glaze forms and pour on top of the baked rolls.
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