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Baked wreath of cinnamon challah bread on a metal pan with white parchment paper.

Cinnamon Sugar Challah

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A fantastic twist on the traditional challah bread with a cinnamon sugar filling. 

  • Total Time: 3 hours
  • Yield: 2 medium braids

Ingredients

Units

For the bread:

  • 7 1/2 to 8 cups all-purpose flour
  • 2 1/2 cups warm water
  • 2 tablespoons active dry yeast
  • 1/3 cup + 1 tablespoon sugar
  • 3 large eggs, at room temperature
  • 1/2 cup vegetable oil
  • 2 teaspoons salt

For the filling:

  • 3 tablespoons heavy cream
  • 4 tablespoons sugar
  • 1 1/2 teaspoons ground cinnamon

Instructions

For the bread:

  1. In a large bowl or the work bowl of a stand mixer, place 6 cups of the flour amount.
  2. Make a well in the center with your hand, pour ½ cup of the water amount, and sprinkle yeast and 1 tablespoon of sugar over the water. Stir the water gently to dissolve the yeast (some of the flour will be incorporated) and let stand for 10 minutes.
  3. Add the remaining sugar and water, eggs, oil and salt and mix with a wooden spoon or the paddle attachment until a shaggy mass is formed. 
  4. If using a stand mixer, knead for 6 or 7 minutes, adding more flour if needed, 1 tablespoon at a time to form a smooth and springy but not dry dough.
  5. If kneading by hand, turn the dough onto a floured surface and knead for 8-10 minutes, adding more flour, 1 tablespoon at a time if needed, to form a smooth and springy but not dry dough.
  6. Place the dough in a greased, deep container. Turn over to coat with oil, cover with film and let rise in a warm, draft-free area until doubled, about 2 to 2 ½ hours. Don't let it rise more than doubled.
  7. Gently deflate the dough down, cover again and let rise until almost doubled about 1 hour.
  8. Deflate the dough again gently.
  9. For the filling, mix the sugar and cinnamon in a small bowl. 
  10. Turn the dough onto a lightly floured work surface and divide it into 2 equal portions. Roll each piece into a rectangle. Brush with half the cream. Sprinkle with half the cinnamon sugar. Repeat with the remaining rectangle.
  11. Roll up like you would cinnamon rolls, starting at the long edge. Transfer the rolls to a greased parchment paper that will fit the baking tray. (You can use two papers and baking trays, or keep half of the dough in the refrigerator while you roll and let the other rise. When ready to bake the first one, take the second piece of dough out, roll, fill and let rise. Bake one at a time).
  12. Cut the roll in two, exposing the filling. Put the ropes side by side and pinch the edges together on one end. Twist the two halves together carefully. Pinch the other end. Bring the two ends together to form a rope. Transfer the parchment paper carefully to the baking tray.
  13. Cover loosely with some foil or parchment paper and let rise until it's spongy but not quite doubled about 45 minutes.
  14. Preheat oven to 350ºF / 180ºC for about 20 minutes before baking.
  15. Bake for 40 to 45 minutes, until the sugar has caramelized, the bread is deeply golden and the bottom sounds hollow when tapped.
  16. Let cool on a wire rack before slicing.

Notes

  • Omit the filling and you have a fantastic challah bread. 
  • Use a different spice instead of or in addition to the ground cinnamon.
  • Author: Paula Montenegro
  • Prep Time: 20 minutes
  • Rising times: 2 hours
  • Cook Time: 40 minutes
  • Category: Bread
  • Method: Baking
  • Cuisine: International