Warm milk, sugar, and active dry yeast in a small bowl until frothy, about 5 minutes.

In a large bowl, whisk flour, sugar, and salt; add eggs, melted butter, and yeast mixture. Stir, then knead until smooth and elastic, about 5–7 minutes.

Place dough in a greased bowl, cover with a clean towel, and set in a warm spot. Let rise until doubled in size, about 1 hour.

Lightly flour your work surface and rolling pin; roll dough into a 12×16-inch rectangle, about ¼-inch thick.

In a bowl, toss cranberries, orange zest, brown sugar, cinnamon, and softened butter until well combined.

Spread the cranberry-orange filling evenly over the dough, then tightly roll from the long edge. Slice into twelve 1½-inch rolls.

Arrange rolls in a greased 9×13-inch pan, cover and let rise in a warm spot until puffy, about 30 minutes.

Preheat oven to 350°F. Bake for 25–30 minutes, until rolls turn golden brown and the filling bubbles at the edges.

Combine powdered sugar, fresh orange juice, and vanilla extract in a bowl; whisk until smooth, creamy, and pourable, about 1–2 minutes.

Drizzle the warm rolls generously with glaze, serve immediately for the best texture and flavor.