In the bowl of a stand mixer fitted with the paddle attachment, stir together warm milk and yeast. Let stand until mixture is foamy, about 5 minutes. Add 2 eggs, ½ cup melted butter, and vanilla, mixing until combined. Add flour, ¼ cup granulated sugar, and salt; beat at low speed until well combined, about 1 minute.
Switch to the dough hook attachment, and beat at low speed until smooth, about 4 minutes. Add dates, cranberries, and orange zest, beating for 2 minutes or until incorporated.
On a lightly floured surface, turn out dough, and shape into a smooth round.
Spray a large bowl with cooking spray. Place dough in bowl, turning to grease top. Cover and let rise in a warm, draft-free place (75°) until doubled in size, about 1½ hours.
Preheat oven to 350°. Line a large rimmed baking sheet with parchment paper.
On a lightly floured surface, turn out dough, and knead until smooth and elastic, about 8 minutes. Divide dough into thirds. Roll one third of dough into a 20-inch-long rope. Repeat with remaining 2 pieces of dough. Braid dough, and place on prepared pan.
In a small bowl, whisk together 1 tablespoon water and remaining 1 egg. Brush top of dough with egg wash. Sprinkle remaining 2 teaspoons granulated sugar.
Bake until top is golden and an instant-read thermometer inserted near the center registers 190°, 45 to 50 minutes, covering with foil halfway through baking to prevent excess browning. Let cool in pan for 15 minutes. Remove from pan, and let cool completely on a wire rack.
For glaze: In a small bowl, mix together confectioners’ sugar, orange zest, and orange juice until smooth. Drizzle over cooked bread before serving.
Recipe by Taste of the South at https://tasteofthesouthmagazine.com/breakfast-brioche-braid/