2 (1/4-oz.) envelopes active dry yeast
1/3 cup plus 1/2 cup sugar, divided
1/2 cup warm milk (100°)
4 1/2 cups all-purpose flour, divided
2 teaspoons kosher salt
1 1/2 cups soft butter, divided
3 large eggs, at room temperature
1 (4-oz.) bittersweet chocolate baking bar, finely chopped
EASY VANILLA GLAZE
Whisk together 2 cups powdered sugar, 3 TBSP milk, ½ tsp vanilla extract, and a dash of table salt. Whisk in up to 1 tbsp milk, ½ tsp at a time until consistency is reached. makes 1½ cups.
- Combine milk, yeast, and 1/3 cup sugar in bowl of a stand mixer; let stand 5 minutes or until foamy. Gradually add 1 cup flour, beating at low speed until blended; scrape down sides. Add salt and 1 cup butter; beat at low speed until smooth. Add eggs, 1 at a time, beating until incorporated after each addition and scraping sides of bowl as needed. Gradually add remaining 3 1/2 cups flour, beating until blended. Increase speed to medium, and beat until dough forms a ball and begins to pull away from sides. Beat dough 2 more minutes or until smooth and elastic. Turn dough out onto a lightly floured surface, and knead 3 minutes.
- Place dough in a large greased bowl, turning to grease top. Cover with plastic wrap, and let rise in a warm place (80° to 85°), free from drafts, 1 hour or until doubled in bulk. Punch dough down, and turn out onto lightly floured parchment paper. Roll dough into a 12- x 18-inch rectangle.
- Brush 6 Tbsp. soft butter over dough; sprinkle with chocolate and 1/2 cup sugar. Roll up dough, jelly-roll fashion, starting at 1 long side. Press edge to seal, and place dough, seam side down, on parchment paper.
- Transfer parchment paper with dough onto a baking sheet. Shape rolled dough into a ring, pressing ends together to seal. Cut ring at 2-inch intervals, from outer edge up to (but not through) inside edge. Gently pull and twist cut pieces to show filling. Cover dough.
- Let rise in a warm place (80° to 85°), free from drafts, 1 hour or until doubled in bulk. Preheat oven to 350°. Uncover dough. Melt remaining 2 Tbsp. butter; brush over dough. Bake 30 to 40 minutes or until golden. Cool on pan 10 minutes. Drizzle Easy Vanilla Glaze over warm bread.