Cinnamon Roll Challah

Recipe provided by Amy Kritzer Becker

Watch the video to learn how to prepare this recipe.

Skill level: Intermediate
Yield: 1 loaf
Nutritional Information per serving: Serving size 1 of 16 servings; Calories 359; Total Fat 10 g; Saturated Fat 1 g; Carbohydrates 62 g; Dietary Fiber 2 g; Sugar 30 g; Protein 7 g; Cholesterol 35 mg; Sodium 211 mg
Total time: 4 hr 35 min (includes resting, rising, and cooling)
Active time: 50 min

Imagine the sweet swirl of cinnamon rolls meets the soft, braided beauty of traditional challahperfect for Rosh Hashanah! This stunning round loaf symbolizes life's sweet cycle, wrapped with gooey cinnamon filling and coiled around a ramekin of irresistible honey glaze dip. It's your showstopping centerpiece that bakes up golden, aromatic, and begging to be torn into for a New Year filled with joy and flavor!

Dough Ingredients:

1 packet (2 1/4 teaspoons) active dry yeast
1/2 cup granulated sugar
1/4 cup vegetable oil, plus extra for greasing the bowl
1/4 cup honey (see Cook's Note)
3 large eggs plus 1 additional yolk
1 1/2 teaspoons kosher salt
4 1/2 to 5 1/2 cups bread flour

Filling Ingredients:

1/3 cup canola oil, plus extra to grease the ramekin
1 cup packed brown sugar
1 tablespoon ground cinnamon
1/8 teaspoon kosher salt

Honey Glaze Dip:

2 tablespoons honey
1/2 cup confectioners' sugar
1 to 2 tablespoons almond milk
2 tablespoons pomegranate arils, for garnish

Instructions:

For the dough: Combine the yeast with 1 tablespoon of the granulated sugar in a large bowl or mixer bowl and add 3/4 cup warm water (approximately 100F) to activate. Let the mixture sit until it becomes foamy, about 10 minutes. If it doesn't foam, the yeast may be inactive or the water temperature incorrect; try again with fresh yeast and water.
Whisk in the vegetable oil, honey, 3 whole eggs, and the remaining sugar into the yeast mixture. Then add salt and about half of the flour, mixing into a rough dough with a wooden spoon or dough hook. Knead for about 10 minutes until smooth, adding more flour as needed until the dough feels soft, smooth, and slightly tacky but not sticky. You may not use all the flour.
Grease a clean bowl and place the dough inside. Cover and allow the dough to rise in a warm spot until doubled, around 2 hours.
For the filling: In a medium bowl, whisk together canola oil, brown sugar, cinnamon, and salt.
Divide the dough evenly into 3 portions. Set two pieces aside. Roll out one piece into a 1/4-inch thick rectangle about 13 by 18 inches. If the dough resists stretching, let it rest momentarily to relax the gluten. If sticky, dust lightly with flour. Spread about one-third of the filling evenly over the surface, leaving a 1/2-inch border. Roll it jelly-roll style from the long edge into a long rope. Repeat with the remaining dough and filling. Braid the three ropes together into a challah braid.
Lightly oil the outside of an 8-ounce (or smaller) ramekin and set it on a parchment-lined baking sheet. Coil the braided challah around the ramekin and connect the ends securely. Cover and let rise until the challah looks airy and puffy, about 45 to 60 minutes.
Position an oven rack in the center and heat the oven to 350F.
Beat the remaining egg yolk with 1 1/2 teaspoons water in a small bowl, then brush it generously over the challah. Bake for about 35 minutes until golden brown. Allow to cool slightly.
For the honey glaze dip: While the challah bakes, mix honey and confectioners' sugar with just enough almond milk to create a thick glaze that coats the back of a spoon.
Pour the glaze into the ramekin, sprinkle the challah with pomegranate seeds, and serve.

Cook's tip: When measuring honey, if you measure the oil first using the same cup, the honey will slide out easily!