1 1/4 cups milk, heated to 115°
1 (1/4-oz.) package active dry yeast
1/3 cup sugar
2 tablespoons unsalted butter, melted, plus 16 tablespoons, softened
1 1/2 teaspoons kosher salt
1 large egg, lightly beaten
4 cups flour
1/2 cup packed light brown sugar
1/3 cup orange zest (from about 4 oranges)
3 cups confectioners’ sugar
1 teaspoon orange extract (not optional)
1 teaspoon vanilla extract
1 tablespoon fresh orange juice
Directions:
Make the dough: Combine the milk and yeast in the bowl of a stand mixer fitted with a hook; let sit until foamy, about 10 minutes. Stir in sugar, melted butter, 1 teaspoon kosher salt, and egg; add flour, and mix on low speed until dough forms. Increase speed to medium-high; knead until smooth, about 8 minutes. Transfer to a large bowl and cover with plastic wrap; let sit until dough doubles in size, about 1 1/2 hours.
Meanwhile, beat softened butter, brown sugar, and zest in a bowl (you’ll need to clean the bowl of your mixer before starting this step) on high speed of a mixer until smooth, about 2 minutes. Add remaining salt, confectioners’ sugar, and extracts; beat until smooth, about 2 minutes. Transfer 1/4 cup of the filling to a bowl; stir in orange juice to make an icing.Set filling and icing aside.
Transfer dough to a work surface; using a rolling pin, roll dough into an 18″ × 10″ rectangle, and spread filling evenly over dough. Lift up bottom edge of dough and roll it into a log; trim ends and cut log into 12 rounds. Transfer rounds cut side up to a greased 9″ × 13″ baking dish; cover with plastic wrap.
Chill 6 hours or overnight.
Heat oven to 375°. Uncover rolls and bake until golden brown, about 25 minutes. Drizzle icing over rolls before serving.