Preheat Oven & Prepare Pan: Preheat your oven to 375°F (190°C). Grease a 9-inch round cake pan.
Make Dough: In a medium bowl, combine the Bisquick mix, milk, 2 tablespoons sugar, and 1 teaspoon vanilla extract. Stir until a soft dough forms.
Roll Out Dough: On a surface dusted with additional Bisquick mix, knead the dough a few times. Roll the dough into a rectangle about 1/4 inch thick.
Add Filling: Brush the dough with melted butter, then sprinkle evenly with a mixture of 1/3 cup granulated sugar and cinnamon.
Roll & Cut: Roll up the dough tightly, starting from the long side. Slice the roll into 1-inch thick pieces.
Arrange in Pan: Place the slices, cut side down, in the prepared pan.
Bake: Bake for 20-25 minutes or until golden brown.
Prepare Glaze: While the rolls are baking, mix powdered sugar, milk, and vanilla extract to make the glaze. Adjust the consistency with more milk or sugar as needed.
Finish & Serve: Drizzle the glaze over warm rolls before serving.