Add the milk, starter, egg, sugar, flour, and salt to a mixer bowl. Mix on low speed until there are no dry spots left. After about 3 minutes, add the softened butter a little at a time.

Keep mixing until the dough looks smooth and well combined.

Move the dough to a clean bowl. Cover it and let it rest for 30 minutes. Do 2 sets of stretch-and-folds, with 30 minutes between each.

Let the dough rise at room temperature until it’s about 50% bigger and feels airy and gassy. This usually takes 6–8 hours depending on your room temperature. (Optional: After the first rise, refrigerate the dough for 8–24 hours. This makes shaping easier and helps create cleaner layers.)

To make the filling, combine cranberries, sugar, orange zest, and orange juice in a saucepan over medium heat.

Stir occasionally and cook until the berries burst and the mixture thickens enough to coat a spoon, about 6–10 minutes. Remove from heat, add the butter, stir until melted, then blend until smooth. Let it cool completely.

To make the glaze, whisk together the powdered sugar, melted butter, orange zest, orange juice, vanilla, and enough milk to get a thick but pourable texture. Set aside.

Spread the cranberry-orange filling evenly over the dough, leaving a small border if the dough feels soft. Roll it up tightly from the long side and pinch the seam to seal. Place it seam-side down.

Starting about 1.5 inches (4 cm) from one end, cut the rolled dough lengthwise into 3 long strips, keeping the top end attached. Braid the three strips loosely, alternating the outer pieces over the middle. It’s okay if some filling comes out.

Transfer the braid onto a sheet of parchment paper. Shape it into a circle and pinch the ends together to close. Cover loosely with parchment or lightly oiled plastic wrap, and let it rise in a warm place until puffy and very light, about 1½–4 hours.

Preheat the oven to 375°F (190°C). Place a cast-iron pan or Dutch oven inside while it heats up. Carefully lift the parchment with the wreath and place both into the hot pan. Bake for 22–25 minutes, until deep golden brown and the center reaches about 200°F (93°C). Let it cool for about 10 minutes.

Drizzle or spoon the glaze over the warm wreath. Slice and serve.