Chocolate-Cinnamon "Babkallah"
['1/2 cup whole milk', '1 1/4 ounces. envelope active dry yeast', '4 large egg yolks', '1 teaspoon vanilla extract', '1/2 cup (1 stick) unsalted butter, melted, cooled, plus more', '1/3 cup granulated sugar', '1 teaspoon kosher salt', '3 cups all-purpose flour, plus more', '6 ounces bittersweet chocolate, finely chopped', '1/3 cup (packed) light brown sugar', '1 1/2 teaspoons ground cinnamon', 'All-purpose flour (for surface)', '1/4 cup (1/2 stick) unsalted butter, room temperature', '1 large egg yolk', 'Granulated sugar (for sprinkling)']
Heat milk in a small saucepan until warm. Transfer to a large bowl and whisk in yeast; let sit until foamy, 5-10 minutes.
Whisk in egg yolks, vanilla, and 1/2 cup butter. Add sugar, salt, and 3 cups flour; mix until a shaggy dough forms. Knead dough on a lightly floured surface until supple, smooth, and no longer shiny, 5-10 minutes. Transfer to a large buttered bowl. Cover and let sit in a warm place until doubled in size, 1 1/2-2 1/2 hours.
Mix chocolate, brown sugar, and cinnamon in a small bowl. Turn out dough onto a lightly floured surface; divide into three portions. Shape each into a 12"-long rope. Roll out each rope to a 12x6" rectangle about 1/8" thick. Brush with butter and top with chocolate mixture, pressing gently. Roll up to form a log; pinch seam to seal.
Place logs, seam side down, side by side on a parchment-lined baking sheet. Pinch logs together at one end; braid, then pinch ends together and tuck under. Cover loosely and let sit in a warm place until 1 1/2 times larger, 1-2 hours.
Preheat oven to 350°. Beat egg yolk with 1 tablespoon water in a small bowl. Brush dough with egg wash; sprinkle with granulated sugar. Bake until top is golden brown and "Babkallah" sounds hollow when bottom is tapped, 35-45 minutes. Let cool on a wire rack.
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