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Mix warm milk, yeast, and 1 teaspoon sugar. Let sit 5–10 minutes until foamy.
Add flour, salt, remaining sugar, eggs, vanilla, and yeast mixture. Knead in butter and continue kneading for 8–10 minutes until smooth and elastic. Cover and let rise until doubled, about 1–1½ hours.
Mix all caramel sauce ingredients together and spread evenly into a greased 9x13 baking dish.
Combine filling ingredients until crumbly.
Roll dough into a 12x18-inch rectangle. Brush lightly with melted butter, then spread filling evenly over the dough.
Roll tightly from the long side and cut into 12 rolls. Place into the caramel-lined baking dish.
Pour ⅛ cup heavy cream between the rolls.
Cover and let rise 30–45 minutes until puffy.
Bake at 350°F for 25–30 minutes or until golden brown.
Beat frosting ingredients together until smooth and spread over warm cinnamon!