In a bowl, combine warm milk and sugar. Stir in yeast; let sit for 5 minutes until frothy. Add melted butter, eggs, and vanilla; mix well.
Gradually add flour, stirring until sticky dough forms. Knead on a floured surface for about 8 minutes until smooth. Place in an oiled bowl, cover, and let rise for 1 hour until doubled.
Roll out dough into a rectangle. Spread softened butter, sprinkle with sugar, and evenly distribute cherries.
Roll up tightly from one edge, slice into rolls, and place cut-side up in a greased baking dish. Let rise again for 30 minutes.
Preheat oven to 375°F (190°C). Bake for about 25 minutes until golden brown.
For the glaze, whisk together powdered sugar and milk until smooth; drizzle over warm rolls before serving.
