In a medium bowl, combine ½ cup of softened unsalted butter, ¼ cup of granulated sugar, and 1 tablespoon of cinnamon. Mix until creamy and smooth. Set aside.

Preheat your oven to 375°F (190°C) and prepare a baking sheet lined with parchment paper.

Unwrap the refrigerated crescent dough and separate it into 8 wedges.

Spread the cinnamon butter mixture evenly over each wedge from the wide end to the point.

Starting from the wide end, roll each wedge tightly towards the point and place seam-side down on the baking sheet.

(Optional) Chill the assembled rolls in the refrigerator for at least 15 minutes.

Bake the rolls for 10-12 minutes until golden brown and puffed up.

While the rolls cool, whisk together 1 cup of powdered sugar, 2 tablespoons of milk, and ½ teaspoon of vanilla extract until smooth.

Drizzle the icing over warm rolls before serving.