Makes: 6 large rolls | Active prep time: 30 minutes | Rest time: 2 hours | Cook time: 40 minutes
1 envelope rapid-rise yeast (0.25 ounce)
1/4 cup warm water
3/4 cup whole milk
1/2 cup softened butter, divided
3 1/2 cups all-purpose flour, divided
1/2 cup sugar
1/3 cup cocoa powder, sifted
1 teaspoon kosher salt
1 egg plus 1 egg yolk
1 teaspoon pure vanilla extract
1/2 cup brown sugar
1 1/2 teaspoons ground cinnamon
1/2 cup semisweet chocolate chips
2 cups powdered sugar, sifted
3 tablespoons heavy whipping cream
1 teaspoon vanilla extract
1. Stir yeast into warm water; let stand 5 minutes or until foaming. Microwave milk and 1/4 cup butter in a liquid measuring cup for 45 seconds or until warm. Add milk mixture and yeast to a large bowl.
2. Add 1 cup flour, sugar, cocoa, salt, egg (plus yolk) and vanilla to bowl; beat until smooth (about 2 minutes).
3. Add remaining flour by the scoopful until a soft dough forms.
4. Turn dough out onto a floured surface; knead about 8 minutes or until soft. Dough will be sticky, so it’s best to use a stand mixer fitted with a bread hook to achieve the best results.
5. Let dough rest on counter; clean out mixing bowl. Dry well; coat inside with nonstick cooking spray to grease. Set dough in the bowl; cover with a clean kitchen towel.
6. Let dough rise about 1 hour or until doubled in size.
7. Sprinkle flour onto counter; turn dough out, rolling gently into a large rectangle about 1/2 inch thick.
8. Spread with remaining softened butter.
9. Combine brown sugar and cinnamon; sprinkle over butter.
10. Sprinkle evenly with chocolate chips.
11. Roll up from long edges like a jelly-roll; cut into 6 large pieces.
12. Arrange rolls, cut sides up, in a greased cast-iron skillet or a 9- x 9-inch baking dish.
13. Cover loosely with plastic wrap; let rise another hour.
14. Preheat oven to 350°F. Remove plastic wrap; bake rolls 35 to 40 minutes or until slightly browned and set, and chocolate is melted.
15. In a small bowl, combine powdered sugar, cream and vanilla; whisk until smooth. Pour over hot rolls; let set. Serve rolls warm. Any leftovers can be stored in an airtight container up to five days.
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