In a small bowl, stir together the granulated sugar, brown sugar, and cinnamon until they’re perfectly blended. Set it aside—you’ll come back to this sweet mixture when your dough is ready to roll.

Activate the yeast – In a small bowl, mix the warm water, yeast, and 1 tablespoon of sugar. Cover with a towel and let it sit for about 5 minutes. You’ll know it’s ready when it’s foamy and bubbly.

Mix the base – In the bowl of a stand mixer fitted with a dough hook, combine the melted butter, warm milk, salt, cinnamon, and the remaining 4 tablespoons of sugar. Stir in the yeast mixture.

Add the flour – Start with 1 cup of bread flour and mix until smooth. Then add the remaining flour, ½ cup at a time, until the dough comes together. Knead for 1–2 minutes until soft and slightly tacky, but not sticky.

Let it rise – Cover the bowl with plastic wrap and set it in a warm spot. Let the dough rise for about 20 minutes, until slightly puffy.

Roll and Shape

Prepare your pan – Preheat the oven to 350°F. Butter a pie dish or 9-inch round baking pan.

Roll the dough – Punch down the dough, then roll it out on a lightly floured surface into a rectangle, about 10×12 inches. Don’t stress if it’s not perfect.

Add the filling – Spread the softened butter evenly over the dough. Sprinkle the cinnamon sugar mixture on top, then gently press it down so it sticks.

Second rise – Place the rolls swirl-side up in your prepared pan, leaving a little space between each. Let them rise for about 15 minutes while the oven heats.

While the rolls bake, whisk together the butter, powdered sugar, vanilla, and milk until smooth and spreadable. Adjust the consistency as needed with a touch more milk or sugar.

Spread the frosting over the warm rolls and watch it melt into all the nooks and crannies.