Prepare the Dough:
In a small bowl, combine warm milk and yeast. Let sit for 5–10 minutes until frothy.
In a large mixing bowl, combine sugar, melted butter, salt, and eggs. Add yeast mixture and stir to combine. Gradually mix in flour until a soft dough forms.
Knead the Dough:
Knead the dough on a lightly floured surface for 5–7 minutes until smooth and elastic. Place in a greased bowl, cover, and let rise in a warm place for 1–2 hours, or until doubled in size.
Prepare the Filling:
In a small bowl, mix brown sugar and cinnamon. Spread softened butter over the rolled-out dough, then sprinkle evenly with the cinnamon-sugar mixture.
Roll and Cut:
Roll the dough into a 16x12-inch rectangle. Starting from the long side, roll tightly into a log. Cut into 12 even rolls and place in a greased 9x13-inch baking dish.
Second Rise:
Cover rolls and let rise for 30–45 minutes until puffy.
Bake:
Preheat oven to 350°F (175°C). Bake rolls for 20–25 minutes until golden brown.
Prepare the Glaze:
While rolls are baking, whisk together powdered sugar, milk, and vanilla until smooth. Drizzle over warm rolls after baking.
Serve:
Enjoy warm for the best flavor and texture.