How to Make It
Prepare the Bread: Stir together warm water, active dry yeast, and 1 teaspoon of the granulated sugar in a small bowl. Let stand until foamy, about 5 minutes.
Beat unsalted butter with a heavy-duty electric stand mixer on medium speed until creamy, about 1 minute. Add salt and 1/2 cup of the granulated sugar; beat until light and fluffy, about 3 minutes. Add eggs, 1 at a time, beating well after each addition. Stir in whole milk and yeast mixture. Gradually add 4 1/2 cups of the bread flour, beating on medium-low just until combined.
Turn dough out onto a lightly floured work surface. Knead until smooth and elastic, about 5 minutes, adding up to 1/2 cup flour, in very small amounts, if necessary to keep dough workable. Place dough in a lightly greased bowl, turning to coat all sides. Cover and let stand in a warm place until dough doubles in size, about 1 hour and 30 minutes.
Combine frozen cranberries, orange zest, and remaining 1/4 cup granulated sugar in a medium bowl. Set aside.
Turn dough out onto a lightly floured work surface. Divide dough in half. Roll 1 dough half into a 16- x 10-inch rectangle, and cut into 8 (5- x 4-inch) rectangles. Spoon about 1 tablespoon of the cranberry mixture on each rectangle. Fold rectangles in half over filling so that short sides meet. Then stand, cut side up and folded side down, in a lightly greased 8- x 4-inch loaf pan. Repeat with second dough half and remaining cranberry mixture in a second loaf pan. Cover pans loosely with plastic wrap, and let stand in a warm place until dough doubles in size, about 1 hour.
Preheat oven to 350°F. Remove and discard plastic wrap. Bake in preheated oven until golden brown and a wooden skewer inserted in center comes out clean, about 30 minutes, shielding with aluminum foil after 20 minutes to prevent excess browning, if necessary.
Cool in pans 10 minutes. Transfer from pans to wire rack to cool slightly, at least 10 minutes.
Prepare the Icing: While Bread cools, beat cream cheese, butter, and salt with an electric mixer on medium speed until creamy. Gradually add powdered sugar, beating until combined. Stir in vanilla extract and 1 tablespoon of the orange juice. Stir in up to 1 more tablespoon orange juice, 1 teaspoon at a time, until it’s smooth and creamy.
Drizzle Bread lightly with Icing, and serve with remaining Icing on the side for dipping.