1. 1. Prepare Your Work Surface and Oven: Preheat your oven to 375 F (190 C). Lightly grease a baking sheet or line it with parchment paper for easy cleanup. This prevents sticking and ensures even baking.

2. 2. Unroll the Crescent Dough: Carefully unroll the crescent roll dough onto your prepared baking sheet or a clean, lightly floured surface. Do not separate the individual triangles. You want to keep it as one large rectangle. If there are perforations, gently pinch them together to form a solid sheet.

3. 3. Create the Berry Filling: In a small bowl, combine the mashed raspberries, granulated sugar, melted butter, and ground cinnamon. Stir these ingredients together until they are well combined and form a thick, spreadable mixture. The sugar will help draw out the raspberry juices, creating a lovely sweet and tart filling.

4. 4. Spread the Filling Evenly: Using a spoon or an offset spatula, spread the raspberry mixture evenly over the entire surface of the crescent roll dough, leaving a small border (about 1/2 inch) along one of the longer edges. This border will help seal the roll later.

5. 5. Roll Up the Dough: Starting from the long edge opposite the border you left, carefully and tightly roll the dough into a log. Take your time to ensure it’s rolled snugly, which helps the rolls hold their shape during baking.

6. 6. Slice the Sweet Rolls: Using a sharp knife or a piece of unflavored dental floss, cut the log into 8-10 even slices, about 1 to 1 1/2 inches thick. Place these slices cut-side up on your prepared baking sheet, leaving a little space between each one for expansion.

7. 7. Bake Until Golden: Bake for 12-15 minutes, or until the rolls are golden brown and cooked through. Keep an eye on them, as oven temperatures can vary. The edges should be nicely browned, and the centers should feel set.

8. 8. Prepare and Drizzle the Glaze: While the rolls are cooling slightly, whisk together the powdered sugar, milk, and vanilla extract in a small bowl until smooth and pourable. If the glaze is too thick, add a tiny bit more milk; if too thin, add a little more powdered sugar. Drizzle the warm rolls generously with the glaze before serving.