The most delicious Challah with Butternut Squash and Onion Filling for Rosh Hashanah

Ingredients (for a ring mold with a diameter of 10-11 inches):

• 3 1/2 cups + 1 tablespoon (about 17.6 ounces) flour
• 2 teaspoons dry yeast
• 1/2 teaspoon baking powder
• 1/4 cup olive oil
• 3 tablespoons sugar
• 1 teaspoon salt
• 1 cup (8 fluid ounces) water

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(Photo: Daniel Laila)

• 1 butternut squash, peeled and coarsely chopped
• 2 cloves of garlic, peeled
• 1/4 cup olive oil
• 1 large onion, peeled and chopped
• 4 sage leaves, chopped
• 1/4 teaspoon grated nutmeg
• 6 rosemary needles, chopped
• 1 heaping teaspoon salt
• 1 tablespoon sugar or honey

• 3 tablespoons olive oil + 1/2 teaspoon sweet paprika

Preparation:

1. The Dough: Combine all the ingredients in a mixer bowl and mix. Knead for about 6 minutes until the dough is smooth and elastic. Cover the bowl loosely with plastic wrap and let it rise for 8-12 hours in the refrigerator (recommended) or for about 1 to 1.5 hours at room temperature until the volume doubles.
2. Meanwhile, prepare the filling: Steam the butternut squash and garlic cloves in a steaming basket over a pot of water or in the microwave until they soften (about 15 minutes). Remove and coarsely mash the butternut squash and separately mash the garlic.
3. Heat the olive oil in a pan and sauté the onion for about 10 minutes over medium-low heat until golden. Add the spices, sugar (or honey), and mashed garlic and mix. Remove from the heat. Add to the mashed butternut squash and mix. Allow to cool completely (can be prepared up to 3 days in advance and stored in the refrigerator).
4. Grease the baking mold. Lightly flour a work surface and place the dough on it. Roll it out into a sheet about 1/4 to 1/3 inch thick (approximately 16x12 inches). Spread the filling over the dough and roll it into a log. Cut the log lengthwise and twist the two halves so the cut side faces upwards. Twist the two parts together like a braid. Transfer to the mold and pinch the ends together. Cover loosely with plastic wrap and let rise near the warming oven until the dough rises by about 70%.
5. Preheat the oven to 375°F (no need for convection).
6. Bake the challah for about 45 minutes until browned on top. Remove and brush, while hot, with the oil mixed with paprika. Allow to cool and serve warm or at room temperature.